Name: 924-88-9|Diisopropyl succinate|98%
Brand: Ambeed
SKU: A136412
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1
[ 924-88-9 ]
[ 6609-56-9 ]
[ 119273-54-0 ]

Yield	Reaction Conditions	Operation in experiment
400 mg (2.4%)	With potassium tert-butylate;	EXAMPLE 2 3,6-Bis(2'-methoxyphenyl)-2,5-dihydropyrrolo(3,4-c)-pyrrole-1,4-dione 12.51 g (93.95 mmol) of 2-methoxybenzonitrile, 10.75 g of potassium tert-butylate and 9.57 g (46.8 mmol) of <strong>[924-88-9]diisopropyl succinate</strong> are reacted analogously to the directions in Chem. Ber. 120, 1075-1078 (1987) and the mixture is worked up. Yield 400 mg (2.4%) of dark red iridescent crystals. Melting point 336-337 C. (dec. from toluene).

Reference： [1]Angewandte Chemie,1989,vol. 101,p. 497 - 499
[2]Patent: US5354869,1994,A

2
[ 924-88-9 ]
[ 704864-71-1 ]

Reference： [1]Tetrahedron Letters,1984,vol. 25,p. 669 - 670

3
[ 543-20-4 ]
[ 67-63-0 ]
[ 924-88-9 ]

Reference： [1]Synthesis,1987,p. 59

4
[ 924-88-9 ]
[ 623-00-7 ]
[ 84632-54-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tert-Amyl alcohol; sodium; iron(III) chloride; at 85 - 95℃; for 12h;	In 100mLSodium (2.01 g, 87 mmol) was added to the two-necked flaskAdd to stirred ferric chloride (10 mg),2-methyl-2-butanol (50 ml) as a solution,Heat to reflux until sodium is completely consumed.Then the solution is cooled to 85C,Then compound 1 (9.09 g, 58 mmol) was added.Diisopropyl succinate (5.27 g, 26 mmol), the mixture was stirred at 95C for 12 hours,After cooling to 50 C.The reaction was quenched by the addition of glacial acetic acid (5 ml) in a solution of methanol (30 ml).The mixture was stirred at 50 C for 30 minutes.The resulting dark brown mixture was then poured into methanol (100 ml).Then filter operation,Collect the precipitate,Wash with 3 parts water and methanolVacuum drying overnight to obtain dark red/purple powder 2 (yield 9.38g, producedThe rate is 82%).
81.5%	With sodium tert-pentoxide; at 20 - 100℃; for 4h;Neat (no solvent);	2-kilo mole of a nitrile of the formula R-CN, WHEREIN R has the meaning indicated in Table 1, and 3960 g of sodium TERT-AMYLATE ARE placed at 20-25 C in a 10000 ml paddle drier (TURBUDRYT), Drais Mannheim Germany). The mixture is heated under nitrogen to the temperature indicated in Table 1. As soon as this temperature has been reached, 2626 ML of <strong>[924-88-9]di-isopropyl succinate</strong> are added by means of a metering pump over the period of time also indicated in Table 1 and with continuous stirring. The indicated temperature is maintained and the alcohol mixture formed is allowed to distil off. When the addition is complete, the reaction mixture is kept at the same temperature for 2 hours and hydrolysed and worked up as in Example 2 to give the pigments of the formula XXII wherein R has the meaning given in Table 1, in the indicated yield.
71.6%	With sodium; In tert-Amyl alcohol; at 90℃; for 12h;Inert atmosphere;	Sodium (4.6 g, 0.2 mol) was cut into pieces and slowly added to 100 mL anhydrous tert-amyl alcohol in a two-neck flask. After stirring for 3 h, 4-bromobenzonitrile (18.2 g, 0.1 mol) was added to the flask and 8 mL <strong>[924-88-9]diisopropyl succinate</strong> dissolved in 30 mL anhydrous tert-amyl alcohol was dropwise added to the reaction mixture under N2 atmosphere. Then the mixture was stirred for 12 h at 90 C, upon cooling the mixture was washed with acetic acid and water. After vacuum drying, 11.5 g red solid was obtained. Yield: 71.6%. The product was used without further purification.

65%	With iron(III) chloride; sodium; In tert-Amyl alcohol; at 50 - 90℃;	Sodium (2.3g, 100mmol) dissolved in 50mL t-amyl alcohol at about 90C over 1h with catalytic amount of FeCl3. The solution was cooled to 50C, 4-bromobenzonitrile was added, and the mixture was heated to 90C, then diisopropylsuccinate (5.05g, 25mmol) in 20mL t-amyl alcohol was added drop-wisely over 2h. Subsequently, the resulting suspension was stirred for 3h at 120C, the reaction mixture was then cooled to 50C. Glacial acetic acid was slowly added and refluxed for 30min, 100mL methanol and water (1/2) were added, the mixture was refluxed for another 2h. After filtration and dry, a bluish-red solid was obtained. (7g, yield: 65%). (The decomposition temperature of compound 1 was proved to be greater than 400C according to TGA results, which were consistent with reported literature.) [11].
65%		Sodium (2.30 g, 100 mmol) was dissolved in 50 mL t-amylalcohol at about 90 C over 1 h with a catalytic amount of FeCl3. Thesolutionwas cooled to 50 C, then 4-bromobenzonitrile was added,and the mixture was heated to 90 C, then <strong>[924-88-9]diisopropyl succinate</strong>(5.05 g, 25 mmol) in 20 mL t-amyl alcoholwas added dropwise over2 h. Subsequently, the resulting suspension was kept for 3 h at120 C, the reaction mixturewas then cooled to 50 C. Glacial aceticacid was slowly added and refluxed briefly, 100 mL methanol and water (1/2) were added, the mixture was refluxed for 3 h. Afterfilteration and dry, bluish-red solid was obtained (7.00 g, 65%).
58%		Compound 3 was prepared according to the literature procedure [8a], with some modifications. Sodium (0.758 g, 32.96 mmol) was dissolved in tert-amyl alcohol (40 mL) under argon atmosphere at 80 C with a catalytic amount of anhydrous FeCl3. After the addition of 4-bromo-benzonitrile (3.00 g, 16.48 mmol) at room temperature, the reaction mixture was heated at 95 C and then a solution of <strong>[924-88-9]di-isopropyl succinate</strong> (1.667 g, 8.24 mmol) in t-AmOH (10 mL) was added dropwise in 7 h. The resulting red suspension was stirred at 95 C for 17 h, cooled to 60 C and then a solution of water (100 mL) and acetic acid (7 mL) was slowly added. The mixture was filtered and the cake was washed with water and methanol until the mother liquor are colorless. The product was dried under vacuum at 60 C for 24 h to give 3 (2.138 g, yield: 58%) as dark-red pigment. EA (calculated): C (48.46), H (2.26), N (6.28)/(found): C(48.23), H (2.09), N (6.32). 1H NMR ((CD3)2SO, 400 MHz), delta (ppm): 8.40 (4H, d, J = 8.1 Hz), 7.82 (4H, d, J = 8.1 Hz). 13C chemical shifts were not determined due to a very low solubility of the sample. IR (KBr), cm-1: 3434, 3131, 3075, 3025, 2969, 2829, 1636, 1600, 1552, 1490, 1437, 1390, 1317, 1275, 1191, 1135, 1071, 1029, 1006, 833, 816, 746, 69, 620, 469.
50%	With potassium tert-butylate; In tert-Amyl alcohol; at 95℃; for 4.42h;Reflux;	In a 100 ml three-neck round bottom flask, 5.46 g (30 mmol) of p-bromobenzonitrile, 20 ml of t-amyl alcohol,5.05 g (45 mmol) of potassium t-butoxideWas added and heated to 95 C with stirring. To this mixture,t-amyl alcohol A solution obtained by dissolving 2.73 g (13.5 mmol) of <strong>[924-88-9]diisopropyl succinate</strong> in 3 mL was added dropwise over 25 minutes.After the dropwise addition, the reaction mixture was heated to reflux for 4 hours and then cooled to 50 C .Water (15 ml) and methanol (15 ml) were added to the mixture and stirred for 30 minutes, and the precipitate was filtered. The obtained red powder was washed with 50% aqueous methanol and water, and vacuum-dried at 80 C to obtain 3.0 g (yield 50%) of Compound 1 as a red powder.
		87 g of tert-amyl alcohol are reacted under inert gas with 11.1 g of sodium at1300C (bath temperature) to form sodium tert-amylate. A mixture, heated to 60C, of 47.2 g of 4-bromobenzonitrile, 23.6 g of <strong>[924-88-9]succinic acid diisopropyl ester</strong> and 54.5 g of tert-amyl alcohol is <n="35"/>then metered in over 2 hours, the internal temperature being lowered to 85C. Then a further 8.2 g of <strong>[924-88-9]succinic acid diisopropyl ester</strong> are subsequently metered in over 3 hours. The resulting suspension is stirred for a further 18 hours and is then cooled to 45C. The suspension is then metered into a mixture, previously prepared and cooled to -100C, of 100 g of methanol, 200 g of ice/water, 23 g of a 10 % aqueous suspension of the product according to Example 2 of EP 0485337 and 25.4 g of sulfuric acid over 30 minutes, the temperature being maintained between -9C and -2C by jacket cooling and by adding, in portions, a further 370 g of ice. After the addition is complete, the reaction vessel is rinsed with 15 g of tert-amyl alcohol and this mixture is added to the protonation mixture. Stirring is then carried out for a further 2.5 hours at -2C to complete the reaction, and the red suspension is divided into two portions of equal size.Example 6A: The first half of the suspension according to Example 6 is filtered and the filter cake is washed first with 500 g of water and then with 1200 g of methanol and finally with 5000 g of water again until the washings are colourless and salt-free and it is then dried for 18 hours at 800C / 104 Pa. There are obtained 25.5 g of a finely divided pigment of the main formula The analytical data correspond to those of Example 1.Example 6B: The second half of the suspension according to Example 6 is filtered in analogous manner to Example 6A but is washed at 00C, the respective wash solutions also having been previously cooled to 00C. After drying there are obtained 25.5 g of a finely divided pigment of the main formula The analytical data correspond to those of Example 1.
	With tert-Amyl alcohol; sodium tert-pentoxide; at 90 - 100℃; for 4h;Molecular sieve; Inert atmosphere;	200 parts of tert-amyl alcohol dehydrated by molecular sieve under nitrogen atmosphere and 140 parts of sodium tert-amyl alkoxide were added to a stainless steel reaction vessel equipped with a reflux pipe, and the mixture was heated to 100 C. with stirring, and the alcoholate solution . Meanwhile, a glass flask was charged with 88 parts of <strong>[924-88-9]diisopropyl succinate</strong> and 153.6 parts of 4-bromobenzonitrile, and heated to 90 C. with stirring to dissolve them, to prepare a solution of these mixtures. The heated solution of this mixture was slowly added dropwise at a constant rate over 2 hours to the alcoholate solution heated to 100 C. with vigorous stirring. After completion of the dropwise addition, heating and stirring was continued at 90 C. for 2 hours to obtain an alkali metal salt of a diketopyrrolopyrrole compound. Further, 600 parts of methanol, 600 parts of water and 304 parts of acetic acid were added to a reaction vessel equipped with a glass jacket and cooled to -10 C. While cooling the cooled mixture with a high-speed stirred disperser at 4000 rpm, the alkali metal salt solution of the diketopyrrolopyrrole compound obtained above cooled to 75 C. was added thereto little by little did. At this time, while cooling, while maintaining the temperature of the mixture consisting of methanol, acetic acid, and water always at a temperature of -5 C. or less, the rate at which the alkali metal salt of the diketopyrrolopyrrole compound at 75 C. is added Was added little by little over approximately 120 minutes while adjusting. After addition of the alkali metal salt, red crystals precipitated and a red suspension was formed. Subsequently, the obtained red suspension was washed with an ultrafiltration device at 5 C. and filtered to obtain a water paste of a diketopyrrolopyrrole pigment represented by the formula (1). Subsequently, the water paste of the resulting diketopyrrolopyrrole pigment was dried at 80 C. for 24 hours and pulverized to obtain 150.2 parts of pigment A1.
	With sodium tert-pentoxide; at 100℃; for 2.5h;Inert atmosphere;	In a 2 L glass flask equipped with a reflux condenser,Under a nitrogen atmosphere,600 parts of tert-amyl alcohol,110 parts of sodium-tert-pentoxide,100 parts of 4-bromobenzonitrile was added,The mixture was heated to 100 C. with stirring,To prepare mixed solution 1.On the other hand, in a 500 ml glass flask,100 parts of tert-amyl alcohol,60 parts of <strong>[924-88-9]diisopropyl succinate</strong> was added,The mixture was heated to 90 C. with stirring,To prepare mixed solution 2.after that,The mixed solution 1 heated to 100 C. was vigorously stirred,The mixed solution 2 heated to 90 C. was slowly added dropwise to the mixed solution 1 over a period of 30 minutes at a constant rate.After completion of the dropwise addition,100 C for 2 hours,Heating stirring was continued,An alkali metal salt solution of a diketopyrrolopyrrole pigment was obtained.The obtained alkali metal salt solution of the diketopyrrolopyrrole pigment was spontaneously allowed to cool to 70 C.,It was filtered with a Nutsche.The filtrate was poured into 1500 parts of water,After stirring at 85 C. for 2 hours,Filtration with Nutsche,Washing with water was repeated until the pH of the filtrate became 8 or less.after that,Dried at 90 C. for 20 hours,And pulverized to obtain 92 parts of the compound (P) having the following structure.
112 g	With sodium tert-pentoxide; In tert-Amyl alcohol; at 85 - 100℃; for 15h;Inert atmosphere;	Into a 500 mL three-necked flask under a nitrogen atmosphere, 176.3 g of anhydrous tert-amyl alcohol (2.0 mol) and 114.7 g of sodium tert-amyl alkoxide (1.1 mol) were charged, and the internal temperature was raised to 100 C. while stirring to react to prepare an alcoholate solution. In a separate 500 mL three-necked flask, 84.9 g of <strong>[924-88-9]diisopropyl succinate</strong> (0.4 mol) and 145.6 g of 4-bromobenzonitrile (0.8 mol) were charged and the internal temperature was raised to 85 C. with stirring To prepare a mixed solution.While the internal temperature of the three-necked flask containing the alcoholate solution was adjusted to 100 C., the above mixed solution was added dropwise over 3 hours with stirring. After completion of the dropwise addition, the mixture was heated and stirred at an internal temperature of 90 C. for 12 hours to obtain a suspension. In another 500 mL three-necked flask, 640 g of methanol (20.0 mol), 720 g of water (40.0 mol) and 300 g of acetic acid (10.0 mol) were charged and stirred while cooling the internal temperature to -10 C. To obtain a mixture. While stirring at high speed while keeping the inner temperature of the above-mentioned mixture in a three-necked flask at -5 C. or lower, the above suspension was added dropwise over 3 hours. After completion of the dropwise addition, the mixture was further stirred for 7 hours, and then the reaction solution was washed and filtrated until coloring of the filtrate and precipitation of salt disappeared. The collected filtrate was dried at 80 C. for 24 hours, and the obtained solid was pulverized to obtain 112 g of a diketopyrrolopyrrole pigment (S-1) having a bromine group represented by the general formula (2).
	With sodium tert-pentoxide; In tert-Amyl alcohol; at 90 - 100℃; for 4h;Inert atmosphere; Molecular sieve;	In a stainless steel reaction vessel equipped with a reflux pipe,Under a nitrogen atmosphere,200 parts of tert-amyl alcohol dehydrated by molecular sieve,And 140 parts of sodium-tert-amyl alkoxide were added,The mixture was heated to 100 C. with stirring,Alcoholate solution was prepared.On the other hand,In a glass flask,88 parts of <strong>[924-88-9]diisopropyl succinate</strong>,153.6 parts of 4-bromobenzonitrile was added,And heated to 90 C. with stirring to dissolve,A solution of these mixtures was prepared.The heated solution of this mixture was added dropwise,To the alcoholate solution heated to 100 C.,With vigorous stirring,Was slowly added dropwise over a period of 2 hours at a constant rate.After completion of the dropwise addition,90 C. for 2 hours,Heating stirring was continued,An alkali metal salt of a diketopyrrolopyrrole compound was obtained.further,In a reaction vessel equipped with a glass jacket,600 parts of methanol, 600 parts of water,And 304 parts of acetic acid were added,It was cooled to -10 C.This cooled mixture was added dropwise,Using a high speed stirred disperser,While rotating a shear disk having a diameter of 8 cm at 4000 rpm,In this,The alkali metal salt solution of the diketopyrrolopyrrole compound obtained above, which was cooled to 75 C.,Was added little by little.On this occasion,methanol,Acetic acid,And water is always maintained at a temperature of -5 C. or less,While cooling, the amount of the alkali metal salt of the diketopyrrolopyrrole compound at 75 C. was adjusted while adjusting the rate of addition, little by little over approximately 120 minutes. After addition of the alkali metal salt, red crystals precipitated and a red suspension was formed. Subsequently, the obtained red suspension was washed with an ultrafiltration device at 5 C. and then filtered to obtain a red paste. This paste was redispersed in 3500 parts of methanol cooled to 0 C. to prepare a suspension having a methanol concentration of about 90%, and stirred at 5 C. for 3 hours to effect particle size regulation accompanied by crystal transition and washing. Subsequently, the diketopyrrolopyrrole-based compound was filtered off with an ultrafiltration machine, and the obtained water paste of the diketopyrrolopyrrole compound was dried at 80 C. for 24 hours and pulverized to obtain diketopyrrolo represented by the formula (1) 150.8 parts of a pyrrole pigment was obtained.
		In a stainless steel reaction vessel equipped with a reflux tube, under a nitrogen atmosphere,200 parts of tert-amyl alcohol dehydrated by molecular sieve, and sodium-tert-Amyl alkoxideAdd 140 parts,The mixture was heated to 100 C. with stirring to prepare an alcoholate solution. On the other hand, 88 parts of <strong>[924-88-9]diisopropyl succinate</strong> and 153.6 parts of 4-bromobenzonitrile were added to a glass flask and heated to 90 C. with stirring to dissolve, thereby preparing a solution of these mixtures. A heated solution of this mixture was slowly dropped into the above-mentioned alcoholate solution heated to 100 C. at a constant rate over 2 hours while stirring vigorously. After completion of the dropwise addition, heating and stirring were continued at 90 C. for 2 hours to obtain an alkali metal salt of a diketopyrrolopyrrole-based compound. Further, 600 parts of methanol, 600 parts of water and 304 parts of acetic acid were added to a reaction vessel equipped with a glass jacket, and cooled to -10 C. The cooled mixture was cooled to 75 C. while rotating a shear disk having a diameter of 8 cm at 4000 rpm using a high-speed stirring disperser, and the alkali metal salt of the diketopyrrolopyrrole compound obtained earlier was cooled to 75 C. The solution was added in small portions.At this time, the rate of addition of the alkali metal salt of the diketopyrrolopyrrole-based compound at 75 C. is kept so that the temperature of the mixture of methanol, acetic acid, and water is always kept at -5 C. or lower. Was adjusted in small portions over approximately 120 minutes.After the addition of the alkali metal salt, red crystals precipitated, and a red suspension was formed. Subsequently, the obtained red suspension was washed with an ultrafiltration device at 5 C.A red paste was obtained by filtration. This paste was redispersed in 3500 parts of methanol cooled to 0 C. to form a suspension having a methanol concentration of about 90%, and the mixture was stirred at 5 C. for 3 hours to perform particle sizing with crystal transition and washing. Subsequently, the aqueous paste of the diketopyrrolopyrrole-based compound obtained by filtration with an ultrafilter is dried at 80 C. for 24 hours and pulverized to obtain a brominated diketo compound represented by the formula (4). 150.8 parts of a pyrrolopyrrole pigment were obtained.
	With sodium tert-pentoxide; at 90 - 100℃; for 2.5h;Inert atmosphere;	In a 2 L glass flask equipped with a reflux tube, under a nitrogen atmosphere,600 parts by weight of tert-amyl alcohol, 110 parts by weight of sodium-tert-pentoxide,100 parts by mass of 4-bromobenzonitrile was added, and the mixture was heated to 100 C. with stirring to prepare a mixed solution 1.Separately, a mixed solution 2 was prepared by adding 100 parts by mass of tert-amyl alcohol and 60 parts by mass of <strong>[924-88-9]diisopropyl succinate</strong> to a 500 ml glass flask, and heating the mixture to 90 C. with stirring.Thereafter, the mixed solution 1 heated to 100 C. was vigorously stirred, and the mixed solution 2 heated to 90 C. was slowly added dropwise to the mixed solution 1 at a constant rate over 30 minutes. After completion of the dropwise addition, heating and stirring were continued at 100 C. for 2 hours to obtain an alkali metal salt solution of the following compound (11). The resulting alkali metal salt solution of compound (11) was allowed to cool to 70 C.And filtered. The filtrate remaining on the filter paper was poured into 1500 parts by mass of water, stirred at 85 C. for 2 hours, filtered with Nutsche, and repeatedly washed with water until the pH of the filtrate became 8 or less. Thereafter, the mixture was dried and ground at 90 C. for 20 hours to obtain 92 parts by mass of the following compound (11).
	With sodium tert-pentoxide; In tert-Amyl alcohol; at 90 - 100℃; for 4h;Inert atmosphere; Molecular sieve;	In a stainless steel reaction vessel equipped with a reflux tube, under a nitrogen atmosphere,200 parts of tert-amyl alcohol dehydrated with molecular sieves and 140 parts of sodium-tert-amyl alkoxide were added and heated to 100 C. with stirring,An alcoholate solution was prepared.On the other hand, in a glass flask, 88 parts of <strong>[924-88-9]diisopropyl succinate</strong>,4-Bromobenzonitrile (153.6 parts) was added, and the mixture was heated to 90 C. with stirring to dissolve it, thereby preparing a solution of these mixtures. The heated solution of this mixture was slowly added dropwise to the above alcoholate solution heated to 100 C. at a constant rate over 2 hours with vigorous stirring. After completion of the dropping, heating and stirring were continued at 90 C. for 2 hours to obtain an alkali metal salt of a diketopyrrolopyrrole compound. Further, 600 parts of methanol, 600 parts of water, and 304 parts of acetic acid were added to a reaction container with a glass jacket and cooled to -10 C. The cooled mixture was cooled to 75 C. while rotating a share disk having a diameter of 8 cm at 4000 rpm by using a high-speed stirring disperser, and the alkali metal salt of the diketopyrrolopyrrole compound obtained above was obtained. The solution was added in small portions. At this time, the rate at which the alkali metal salt of the diketopyrrolopyrrole compound at 75 C. was added while cooling so that the temperature of the mixture of methanol, acetic acid, and water was always kept at -5 C. or lower. Was added in small portions over approximately 120 minutes. After the addition of the alkali metal salt, red crystals were precipitated and a red suspension was formed. Subsequently, the obtained red suspension was washed with an ultrafiltration device at 5 C. and then filtered to obtain a red paste. This paste was redispersed in 3500 parts of methanol cooled to 0 C. to obtain a suspension having a methanol concentration of about 90%, and the mixture was stirred at 5 C. for 3 hours to perform particle sizing accompanied by crystal transition and washing. Then, filtered with an ultrafilter, the resulting water paste of diketopyrrolopyrrole compound,By drying at 80 C. for 24 hours and pulverizing, 150.8 parts of diketopyrrolopyrrole pigment (Aa) was obtained.

Reference： [1]Chemical Communications,2013,vol. 49,p. 8368 - 8370
[2]Patent: CN107987093,2018,A .Location in patent: Paragraph 0031; 0032
[3]Patent: WO2004/76456,2004,A1 .Location in patent: Page 15-17
[4]Journal of Polymer Science, Part A: Polymer Chemistry,2014,vol. 52,p. 739 - 751
[5]Tetrahedron,2014,vol. 70,p. 7050 - 7056
[6]Dyes and Pigments,2013,vol. 98,p. 232 - 237
[7]Dyes and Pigments,2013,vol. 99,p. 779 - 786
[8]Dyes and Pigments,2013,vol. 96,p. 679 - 685
[9]Chemical Communications,2009,p. 5859 - 5861
[10]Patent: KR2015/46785,2015,A .Location in patent: Paragraph 0235; 0236; 0237
[11]Macromolecules,2006,vol. 39,p. 8347 - 8355
[12]Patent: WO2009/144115,2009,A1 .Location in patent: Page/Page column 32-33
[13]Polymer,2010,vol. 51,p. 1016 - 1023
[14]Chemistry - An Asian Journal,2012,vol. 7,p. 1562 - 1566
[15]Chemical Communications,2014,vol. 50,p. 8747 - 8750
[16]New Journal of Chemistry,2016,vol. 40,p. 6706 - 6713
[17]Patent: JP2016/180042,2016,A .Location in patent: Paragraph 0136
[18]Patent: JP2017/88703,2017,A .Location in patent: Paragraph 0123-0125
[19]Patent: JP2016/176058,2016,A .Location in patent: Paragraph 0116-0120
[20]RSC Advances,2018,vol. 8,p. 30201 - 30206
[21]Patent: JP2018/145312,2018,A .Location in patent: Paragraph 0157
[22]Photochemical and Photobiological Sciences,2019,vol. 18,p. 1064 - 1074
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5
[ 924-88-9 ]
[ 90486-28-5 ]

Reference： [1]Tetrahedron Letters,1984,vol. 25,p. 669 - 670

6
[ 623-03-0 ]
[ 924-88-9 ]
[ 84632-65-5 ]

Yield	Reaction Conditions	Operation in experiment
70.5%	With iron(III) chloride; tert-Amyl alcohol; sodium; at 100 - 120℃; for 3h;	Sodium metal (2.30g, 100mmol), tert-amyl alcohol (50mL) and a catalytic amount of ferric chloride were added to a three-necked reaction flask, after stirring at 100 C for 1 hour, it was cooled to 50 C. After adding p-chlorobenzonitrile (5.48 g, 40 mmol) and heating the mixture to 100 C, a solution of <strong>[924-88-9]diisopropyl succinate</strong> (4.00 g, 20 mmol) in t-amyl alcohol was slowly added dropwise. After completion of the dropwise addition, the reaction was performed at 120 C for 3 hours. Cool to room temperature.Slowly add glacial acetic acid to adjust the pH to 7.0. Methanol and water (1: 2, v: v, 100 mL) were then added and refluxed for 2 hours. Cooled to filter and dried to give a pale red powdery solid (5.01 g). Yield: 70.5%
43%		Under nitrogen condition, potassium tert-butoxide (2.25 g, 0.02 mol) was dissolved in150 mL of tert-amyl alcohol for 15 min and the mixture was heated to 110. Iron(III) chloride (s.a) was added and stirred for 30 min then 4-chlorobenzonitrile (1.5 g, 0.01 mol) was added and stirred for 1 hr at the same temperature. Diisopropyl succinate (1.01g, 0.005 mol) was dissolved in 30 mL of tert-amyl alcohol and dropwised to the mixture for 3 hr. Then 60 mL of water was poured into mixture and stirred for 20 hr at the same temperature. After reaction, the mixture was cooled to room temperature. The mixture was filtered off and washed by water, methanol. The red pigment was purified by 50 mL methanol and stirred for 30 min at 60. After stirring, the solution was filtered off and dried under vacuum to obtain Pigment 1 in 43% yield. C18H10Cl2N2O2, Found C: 60.21 H:2.84 N: 7.73, MS (m/z) 356(M+).
		450.0 parts of t-amyl alcohol and 15.45 parts of solid sodium were poured into separable wide mouth flask of 1L volume equipped with agitating blade made of glass, thermometer, nitrogen inlet tube, reflux condenser, and dropping funnel. The mixture was heated in oil bath at 130 C, and a small amount of iron(III) trichloride was added. After metal sodium vanished pe rfectly, mixture of 45. 51 parts of 4-chlorobenzonitrile, 1.50 parts of 3-methoxybenzonitrile, 50.76 parts of diisopropylsuccinimide and 90.0 parts of t-amyl alcohol was added within 2 hours. Then, reaction liquid temperature was reduced to 85 C, and reaction mixture was stirred for 2 hours more. Temperature was reduced to 40 C, and reaction mixture was poured into next reactor containing mixture of 900 parts of ion exchanged water,900 parts of methanol, and 360 parts of sulfuric acid at 40 C within 30 minutes. Then the pigment was conditioned at 40 C for 18 hours. After filtering and drying, 45.6 parts of crude pigment powder of red 3,6-bis(4-chlorophenyl)-1,4-diketo-pyrrolo[3,4-C]pyrrole (having same chemical structure as C. I. Pigment Red 254 expressed in the above formula). 40 parts of the crude pigment was suspended stirring in 800 parts of dimethylacetamide in separable wide mouth flask of 1L volume, and was further heated stirring at 140 C for 5 hours. After filtering, washing and drying, 37.9 parts of a red pigment was obtained. The pigment had mean particle diameter in the range between 0.40 and 0.70 mum.

		1 18 g of tert-amyl alcohol are reacted under inert gas with 18.4 g of sodium at 1300C (bath temperature) to form sodium tert-amylate. A mixture, heated to 600C, of 56.7 g of 4-chlorobenzonitrile, 37.3 g of <strong>[924-88-9]succinic acid diisopropyl ester</strong> and 118 g of tert-amyl alcohol is then metered in over 2 hours, the internal temperature being lowered to 85C. Then a further 12.4 g of <strong>[924-88-9]succinic acid diisopropyl ester</strong> are subsequently metered in over 3 hours. The resulting suspension is stirred for a further 18 hours and is then cooled to 400C. The suspension is then metered into a mixture, previously prepared and cooled to -10C, of 177 g of methanol, 400 g of ice/ water, 73 g of a 10 % aqueous suspension of the product according to Example 2 of EP 0485337 and 49.5 g of sulfuric acid over 50 minutes, the temperature being maintained between -14C and -8C by jacket cooling and by adding, in portions, a further 800 g of ice. After the addition is complete, the reaction vessel is rinsed with 16 g of tert-amyl alcohol and this mixture is added to the protonation mixture. Stirring is then carried out for a further 2.5 hours at from -8C to +3C to complete the reaction, and filtration is then carried out. The filter cake is washed first with 1000 g of water and then with 3200 g of methanol and finally with 6000 g of water again until the washings are colourless and salt-free and it is then dried for 18 hours at 800C / 104 Pa. There are obtained 73 g of a finely divided pigment mainly of formula The analytical data correspond to those of Example 4.
		31 parts of 4-chlorobenzonitrile are introduced into 30% sodium amoxide (prepared from 9.3 parts of sodium and 143 parts of amyl alcohol) and heated to 100 C. 30 parts of <strong>[924-88-9]diisopropyl succinate</strong> are added within two hours and the pigment salt suspension obtained is subsequently stirred at 100 C. for a further four hours.The thereby obtained disodium salt of the pigment is converted into the pigment by hydrolysis of the hot disodium salt suspension, cooled to 80 C., by pouring onto 420 parts of neutral water.Isolation and washing with methanol and water gives a pigment which has a maximum of the frequency distribution (the mode of the distribution) of the crystalline particles at 167 nm. The BET surface area of the pigment is 63 m2/g.
	With sodium t-butanolate; at 100℃; for 3h;Inert atmosphere;	In the p- chlorobenzonitrile 2,475g, and 100 under the nitrogen (N(sub)2(/sub)) using the "All in one reactor (Drais Mannheim Germany) " the <strong>[924-88-9]diisopropyl succinate</strong> 2,181g and sodium t- butyrate 2,869g, it was stirred for 3hours and it reacted. In 130 the mixture, after it was stirred in 30 min. and it reacted at the addition it cooled to 60. After the reactant was washed with the methanol aqueous solution (50%) of 100 L it dried using the hot air dryer in 150 for 12 hours and the tempering (crude) diketopyrrolopyrrole (DPP red 254) pigment of the red solid powder state was manufactured. The tempering diketopyrrolopyrrole pigment was observed through the transmission electron microscope (transmission electron microscope (TEM): JEM-2000, JEOL, Japan). Then the particle was uneven and cohesion was high and color had the brown color and it was the state that it commercially could not use (fig. 1).
5.01 g		Sodium metal (2.30 g, 100 mmol),Tert-amyl alcohol (50 mL) and a catalytic amount of ferric chloride were added to the three-neck reaction flask, and after stirring at 100 C. for 1 hour, it was cooled to 50 C. After addition of p-chlorobenzonitrile (5.48 g, 40 mmol) the mixture was addedUpon heating to 100C, a solution of <strong>[924-88-9]di-isopropyl succinate</strong> (4.00 g, 20 mmol) in tert-amyl alcohol was slowly added dropwise. After completion of the addition, the reaction was carried out at 120C for 3 hours. Cool to room temperature. Slowly add glacial acetic acid to adjust the pH to 7.0, then add methanol and water (1:2, v:v,100 mL), reflux for 2 hours. Cool filtered and dried to a pale red powder solid (5.01 g).
5.01 g	With iron(III) chloride; In tert-Amyl alcohol; at 100 - 120℃; for 3h;	Sodium metal (2.30 g, 100 mmol), tert-amyl alcohol (50 mL) and a catalytic amount of ferric chloride were placed in a three-necked reaction flask, stirred at 100 C for 1 hour and then cooled to 50 C.Add p-chlorobenzonitrile (5.48g, 40mmol) and add the mixtureHeat to 100 C,A solution of <strong>[924-88-9]diisopropyl succinate</strong> (4.00 g, 20 mmol) in tert-amyl alcohol was slowly added dropwise.After completion of the dropwise addition, the reaction was carried out at 120 C for 3 hours.Cool to room temperature. Slowly add glacial acetic acid to adjust the pH to 7.0, then add methanol and water (1:2, v: v, 100 mL) and reflux for 2 hours.Cool filtered and dried to give a pale red powder solid (5.01 g).

Reference： [1]Patent: US6361594,2002,B1 .Location in patent: Page column 15-16, 17
[2]Patent: CN107602649,2019,B .Location in patent: Paragraph 0043-0044; 0055-0060
[3]Molecular Crystals and Liquid Crystals,2015,vol. 617,p. 73 - 81
[4]Patent: US6361594,2002,B1 .Location in patent: Page column 18-19
[5]Patent: US6361594,2002,B1 .Location in patent: Page column 19
[6]Patent: US6361594,2002,B1 .Location in patent: Page column 18
[7]Patent: US6361594,2002,B1 .Location in patent: Page column 16-17
[8]Patent: US6361594,2002,B1 .Location in patent: Page column 15-16
[9]Patent: EP2055748,2009,A1 .Location in patent: Page/Page column 9
[10]Patent: WO2009/144115,2009,A1 .Location in patent: Page/Page column 32
[11]Patent: US2010/121053,2010,A1 .Location in patent: Page/Page column 4
[12]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 3427 - 3430
[13]Patent: KR2015/134693,2015,A .Location in patent: Paragraph 0026-0027
[14]Patent: CN107652705,2018,A .Location in patent: Paragraph 0090; 0095; 0096
[15]Patent: CN107603272,2019,B .Location in patent: Paragraph 0110-0111; 0116-0117

7
[ 924-88-9 ]
[ 100-47-0 ]
[ 54660-00-3 ]

Yield	Reaction Conditions	Operation in experiment
	With iron(III) chloride; sodium tert-pentoxide; at 50 - 120℃;	General procedure: A mixture of sodium (2.30 g, 100 mmol), t-amyl alcohol (50 mL) and catalytic amount of FeCl3 were added into a three-necked flask under air. After being stirred vigorously at 100 C for 1 h, the mixture was cooled to 50 C, 3 (40 mmol) was added. Then the mixture was heated to 100 C, <strong>[924-88-9]diisopropyl succinate</strong> (4.00 g, 40 mmol) in t-amyl alcohol (20 mL) was added dropwise over 2 h. Subsequently, the resulting suspension was kept for 3 h at 120 C, and cooled to room temperature. Glacial acetic acid was slowly added till pH was 7.0, followed by methanol and water (1:2, v:v,100 mL) added, the mixture was heated under reflux for 2 h. After cooling filtration and dried, the corresponding product was obtained. The product (2) was used without further purification.

Reference： [1]Patent: US6361594,2002,B1 .Location in patent: Page column 14-15
[2]Patent: US6361594,2002,B1 .Location in patent: Page column 15
[3]Tetrahedron,2017,vol. 73,p. 494 - 499

8
[ 924-88-9 ]
[ 2920-38-9 ]
[ 88949-33-1 ]

Yield	Reaction Conditions	Operation in experiment
38%		General procedure: Under nitrogen condition, potassium tert-butoxide (2.25 g, 0.02 mol) was dissolved in150 mL of tert-amyl alcohol for 15 min and the mixture was heated to 110. Iron(III) chloride (s.a) was added and stirred for 30 min then 4-chlorobenzonitrile (1.5 g, 0.01 mol) was added and stirred for 1 hr at the same temperature. Diisopropyl succinate (1.01g, 0.005 mol) was dissolved in 30 mL of tert-amyl alcohol and dropwised to the mixture for 3 hr. Then 60 mL of water was poured into mixture and stirred for 20 hr at the same temperature. After reaction, the mixture was cooled to room temperature. The mixture was filtered off and washed by water, methanol. The red pigment was purified by 50 mL methanol and stirred for 30 min at 60. After stirring, the solution was filtered off and dried under vacuum to obtain Pigment .

Reference： [1]Patent: US6361594,2002,B1 .Location in patent: Page column 17,18
[2]Molecular Crystals and Liquid Crystals,2015,vol. 617,p. 73 - 81
[3]Patent: US6361594,2002,B1 .Location in patent: Page column 18

9
[ 2160-62-5 ]
[ 924-88-9 ]
[ 777079-55-7 ]

Yield	Reaction Conditions	Operation in experiment
7.3%		6.01 G of sodium and 400 ml OF TERT-AMYL ALCOHOL are heated up to 100 C under a nitrogen atmosphere and stirred for 18 hours. The reaction mixture is allowed to cool to room temperature, 44. 66 G OF 2-CYANO-5-BROMOTHIOPHENE ARE added and heated up to 110C. As soon as the temperature has been reached, a solution OF 24. 3G OF DIISOPROPYL SUCCINATE and 100 mi of tert-amyl alcohol is added over 5 hours using a dropping funnel. When the addition has been completed, the reaction mixture is kept for 20 hours at 120C and cooled down to 65C. Then 300ML of water and 20 mi of acetic acid are added and the resultant pigment suspension is filtered at room temperature, washed with methanol and water until washings run colorless, and dried, affording 8. Og (7.3% of theory, based on dibutyl succinate) of 1,4- diketo-3, 6-BIS-2- (5-BROMOTHIOPHENE-YI)-PYRROLO- (3, 4-C)-PYRROLE. Example 3 is repeated, except using A-4 in place OF A-1, whereby a red solid is obtained (yield : 5%)

Reference： [1]Patent: WO2004/90046,2004,A1 .Location in patent: Page 58

10
[ 924-88-9 ]
[ 97483-77-7 ]
[ 777079-50-2 ]

Yield	Reaction Conditions	Operation in experiment
9.8%		3.8 G of sodium and 300 mi of ter-amyl alcohol are heated up to 1 00C under a nitrogen atmosphere and stirred for 15 hours. The reaction mixture is allowed to cool to room temperature. 27.7 G OF 2-CYANO-5-BROMOPYRIDINE are added and heated up to 110C. As soon as the temperature has been reached, a solution of 16.2 G of <strong>[924-88-9]diisopropyl succinate</strong> and 100 mi of tert-amyl alcohol is added over 1 hour using a dropping funnel. When the addition has been completed, the reaction mixture is kept for 20 hours at 1 00C and cooled down to 65C. Then 300MOI of water are added and the resultant pigment suspension is filtered at room temperature, washed with methanol and water until washings run colorless and dried at 100C in vacuum, affording 6.6 G (9.8% of theory, based on dibutyl succinate) of 1,4-diketo- 3, 6-BIS-2- (5-BROMOPYRIDIN-YL)-PYRROLO- (3, 4-C)-PYRROLE

Reference： [1]Patent: WO2004/90046,2004,A1 .Location in patent: Page 56

11
[ 117482-76-5 ]
[ 924-88-9 ]
[ 51238-46-1 ]
[ 646517-01-3 ]
[ 850566-84-6 ]

Yield	Reaction Conditions	Operation in experiment
		25.9 g (1. 13 mol) of sodium cut into small pieces and a spatula tip of FeCI3 are introduced into 250 mi of tert-amyl alcohol in a 1 litre sulfonating flask and heated to reflux (bath tempe- rature of 130C). Into the resulting clear solution there is then added a solution of 107.2 g (0.50 mol) of 4-phenylthiobenzonitrile, 2.1 g (0. 005 mol) of 4-octadecylthiobenzonitrile and 73.43 g (0.36 mol) of <strong>[924-88-9]succinic acid diisopropyl ester</strong> (SAI) in 100 ml of tert-amyl alcohol via a heated dropping funnel (90C) over 3 hours. After the addition is complete, stirring is carried out at reflux for a further 1.5 hours. The reaction mixture is then cooled to room temperature and, over 30 minutes, transferred by means of a pump into a mixture of 1000 ml of water/ice, 200 ml of methanol and 90 g of glacial acetic acid at 0C. After the addition is complete, stir- ring is carried out overnight at 0-10C to complete the reaction. The red suspension is then filtered and washed with methanol and then with water. After drying overnight at 70C and 200 mbar in a drying cabinet, there are obtained 106.3 g (87 % of theory) of a pigment which in PVC results in a transparent, tinctorially strong, red coloration.

Reference： [1]Patent: WO2005/40284,2005,A1 .Location in patent: Page/Page column 36

12
[ 623-03-0 ]
[ 117482-76-5 ]
[ 924-88-9 ]
[ 766-84-7 ]
[ 850566-83-5 ]
[ 88949-44-4 ]

Yield	Reaction Conditions	Operation in experiment
		38.8 g (1.68 mol) of sodium cut into small pieces and a spatula tip of Fecal3 are introduced into 375 mi of tert-amyl alcohol in a 1 litre sulfonating flask and heated to reflux (bath tempe- rature of 130C). To the resulting clear solution there is then added a solution of 72.3 g (0. 53 mol) of 3-chlorobenzonitrile, 31.0 g (0.23 mol) of 4-chlorobenzonitrile, 14.2 g (0. 038 mol) of 4-octadecylthiobenzonitrile and also 92.9 ml (0.45 mol) of <strong>[924-88-9]succinic acid diisopropyl ester</strong> (SAI) in 225 mi of tert-amyl alcohol via a heated dropping funnel over 3 hours, the bath tem- perature being set at 95C at the beginning. After the addition is complete, a further 15.5 mi (0.075 mol) of SAI are added over 30 minutes. The reaction mixture is then cooled to 50C and transferred to a mixture of 375 ml of methanol and 1125 ml of water at room temperature over 30 minutes. After the addition is complete, stirring is carried out overnight to complete the reaction. The orange suspension is filtered and washed with methanol and then with water. After drying overnight at 80C and 200 mbar in a drying cabinet, there are obtained 136.9 g (91 % of theory) of a pigment which in PVC results in a transparent, tinctorially strong, orange coloration.

Reference： [1]Patent: WO2005/40284,2005,A1 .Location in patent: Page/Page column 35-36

13
[ 623-03-0 ]
[ 924-88-9 ]
[ 100-47-0 ]
[ 88949-37-5 ]
[ 84632-65-5 ]
[ 54660-00-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tert-pentoxide; at 20 - 100℃; for 2h;Neat (no solvent);	1.0 kilo mole of a nitrile of the formula R'-CN and 1.0 kilo mole of the formula R"-CN, wherein R'and R"ARE different and are as defined in Table II (Examples 16-20) and 3.4 kilo mole of sodium tert-amylate are placed at 20-25 C in a 10000 ml"All In One REACTOR" (OF, DRAIS Mannheim Germany). By means of a metering pump, 1.2 kilo moles of <strong>[924-88-9]diisopropyl succinate</strong> are added at the reaction temperature indicated in Table II over the period of time also indicated therein, while continuously distilling off the alcohol mixture. When the addition is complete, the mixture is kept for 2 hours at the reaction temperature and then hydrolyse and worked up as in Example 2 to give the pigment mixture of the formulas XXIII, XXIV and XXV of Table 2.

Reference： [1]Patent: WO2004/76456,2004,A1 .Location in patent: Page 18

14
[ 623-03-0 ]
[ 924-88-9 ]
Na₂[(4-Cl-Ph)2diketopyrrolopyrrol] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium t-butanolate; at 20 - 87℃; under 37.5038 - 600.06 Torr;Neat (no solvent);	1527.4 g <strong>[924-88-9]diisopropyl succinate</strong>, 1732.5 g of p-chlorobenzonitrile and 2013 g sodium TERT-BUTYLATE are placed in a 10000 ml"All In One REACTOR" OF (Drais Mannheim Germany) at 20-25 C. Under stirring and nitrogen flow the mixture is heated to 87 C (inside temperature). From 50 C onwards the reaction mixture becomes considerably thicker and is finally converted into a paste. As soon as the inside temperature of 87 C is reached, a vacuum of 800 mbar is applied at the outlet of the condenser which is then gradually reduced to 50 mbar, thereby allowing the mixture of isopropyl alcohol and tart-butyl alcohol to distil off. The inside temperature first drops to 75 C and thereafter rises again to 85 C as soon as the mixture of alcohols is completely distilled off. The reaction mass becomes crumbly and finally largely disintegrates into an almost semi- powdery material. After the distillation of the residual mixture of alcohols, the reaction mixture is stirred for another 30 minutes at 87 C under vacuum of 50 mbar. The mixture is cooled to 60 C and the material is emptied into a steel container. The yield is 2950 g of the crude compound of formula XIX of example 21 of 81. 4% purity (approximately 95% of theory, based on p- chlorobenzonitrile).
90%	With sodium t-butanolate; at 20 - 120℃; for 5h;Neat (no solvent);	2475 g of p-chlorobenzonitrile, 2181. 6 g <strong>[924-88-9]diisopropyl succinate</strong> and 2869. 2 g sodium tert- butylate are placed at 20-25 C in a 10000 ML"ALL In One REACTOR" of (Drais Mannheim Germany). Under stirring and nitrogen flow the mixture is heated to 100 C within 60 minutes. From 80 C onwards the reaction mixture becomes considerably thicker and is finally converted into a paste. From 80-85 C onwards a rapid formation of alcohol vapours is observed. The temperature is maintained at 99 to 100 C for three hours, thereby allowing the mixture of isopropyl alcohol AND TERT-BUTYL alcohol to distil off. The reaction mass becomes crumbly and finally largely disintegrates into an almost semi-powdery material. The reaction mixture is heated to 120 C in 30 minutes and kept at 120 C for 30 minutes. The mixture is cooled to 50 C. The material is emptied into a polyethylene sack, tightly fitted to the outlet of the reactor ; affording 3248 g (90 % of theory, based on p-chlorobenzonitrile) of pigment of the formula XIX. Approximately 200 g (5.54 % of theory, based on p- chlorobenzonitrile) of the product are still contained in the reactor to be used in the next batch. The total yield thus corresponds to approximately 3448 g (approximately 95.54 % of theory, based on p-chlorobenzonitrile). This product produces an intense red colour when dispersed with stirring into a state-of-the- art waterborne paint system.
87%	With sodium isopropylate; at 20 - 120℃; for 6.41667h;Neat (no solvent);	2750 g OF P-CHLOROBENZONITRILE and 2950 g sodium iso-propylate are placed at 20-25 C in a 10000 ML"ALL In One Reactor" of (Drais Mannheim Germany). Under stirring and nitrogen flow the mixture is heated to 90 C within 60 minutes. As soon as this temperature has been reached, 2424 g <strong>[924-88-9]diisopropyl succinate</strong> are added over 145 minutes by means of a metering pump. The temperature is kept CONSTANTLY AT 98-99 C and isopropyl alcohol is distilled off. The temperature is maintained at 99 to 100 C FOR two hours. The reaction mixture is heated to 120 C in 30 minutes and kept at 120 -C FDR 30 minutes. The mixture is cooled to 50 C. The material is emptied into a polyethylene sack tightly fitted to the outlet of the reactor ; the yield is 3490 g (approximately 87% of theory, based on P-CHLOROBENZONITRILE) of the compound of formula XIX. For the hydrolysis, 1000 G of the above reaction mixture is slowly added to 10000 ML of water at 80 C TEMPERATURE. THE resultant pigment suspension is heated to 95 C and kept at 95 C for two hours. Thereafter, it is filtered at about 80 C, washed with water until the washings run colourless, and dried AT 80 C in vacuum ; affording 872 g (98 % of theory, based on the compound of formula XIX) of a very finely divided pigment of the formula XX. The crude pigment is then finished by treating with seven volume parts of dimethyl formamide at 130 C for three hours. The suspension is filtered at 100 C, washed with the same volume of dimethyl formamide heated to 100 C followed by water at 70 C. The press cake is dried at 100 C yielding A bright red product.

A 500 ml glass reactor is charged with 150 ml of ANHYDROUS TER-AMYL alcohol under nitrogen. 4. 6 g (0.2 moles) of sodium are added thereto and the mixture is heated to and maintained at 100- 105 C FOR 12 hours. To the resulting solution are then added at 80 C, 20.6 g (0. 15 moles) of 4- chlorobenzonitrile. Subsequently 20.1 g (0. 01 moles) of <strong>[924-88-9]diisopropyl succinate</strong> are metered in at 96 C. over 3 hours. The isopropanol formed during the reaction along with some ter-amyl alcohol is allowed to distil off simultaneously during the addition. The reaction mixture is stirred for another 4 hours after the. addition OF DIISOPROPYL SUCCINATE. IS complete. Thereafter the reaction mixture is transferred to a 500 ml round bottomed flask and the residual ter-amyl alcohol is distilled off on a rotavap (Buechi). under vacuum to yield the compound of Formula XIX as a dark red powder.

Reference： [1]Patent: WO2004/76456,2004,A1 .Location in patent: Page 20
[2]Patent: WO2004/76456,2004,A1 .Location in patent: Page 13
[3]Patent: WO2004/76456,2004,A1 .Location in patent: Page 15
[4]Patent: WO2004/76456,2004,A1 .Location in patent: Page 23

15
[ 623-03-0 ]
[ 117482-76-5 ]
[ 924-88-9 ]
C₃₆H₄₇ClN₂O₂S [ No CAS ]
[ 84632-65-5 ]

Yield	Reaction Conditions	Operation in experiment
		The reaction is carried out under an inert atmosphere in a 5-necked 1.5 litre sulfonating flask provided with a thermometer, a mechanical stirrer, a dropping funnel and a reflux condenser. The protonation and conditioning step is carried out in a 5-necked 2. 5 litre sulfonating flask provided with a thermometer, a mechanical stirrer and a reflux condenser. 22.96 g (1.0 mol) of sodium are added to a solution of 200 g of tert-amyl alcohol and a cata- lytic amount of Fe (III) CI3 at 112C. The sodium dissolves, with the formation of sodium tert- amylate and H2, over 60 minutes at 112C. Then 66.21 g (0. 48 mol) of p-chlorobenzonitrile, 5.95 g (0.016 mol) of p-octadecylthiobenzonitrile and 48. 16 g (0.238 mol) of <strong>[924-88-9]succinic acid diisopropyl ester</strong> (SAI) are dissolved in 121 g of tert-amyl alcohol at 90C and added over 2 hours to the reaction mixture. In the first hour of addition the internal temperature is main- tained at 112C but is then reduced to 85C. A further 16.06 g (0.08 mol) of SAI are then added over 3 hours and the reaction mixture is stirred at 85C for a further 4 hours and cool- ed to room temperature. The reaction mixture is then transferred into a solution of 552 ml of water and 522 ml of methanol at room temperature over 20 minutes. The resulting mixture is heated to 50C and stirred at that temperature for 4 hours. The dark-red precipitate is then filtered off, washed with 8 litres each of methanol and water and dried at 80C and 200 mbar in a drying cabinet. 88.3 g (96 % of theory) of a red mixture comprising the pigments of for- mulae (103) and (104) are obtained, which in PVC results in a transparent red coloration.
		The reaction is carried out under an inert atmosphere in a 5-necked 1.5 litre sulfonating flask provided with a thermometer, a mechanical stirrer, a dropping funnel and a reflux condenser. The protonation and conditioning step is carried out in a 5-necked 2. 5 litre sulfonating flask provided with a thermometer, a mechanical stirrer and a reflux condenser. 44. 5 g (1.9 mol) of sodium are added to a solution of 348 g of ter-amyl alcohol and a cataly- tic amount of Fe (III) CI3 at 115C. The sodium dissolves, with the formation of sodium tert- amylate and H2, over 40 minutes at 115C. Then 137.6 g (1.0 mol) of p-chlorobenzonitrile, 12.3 g (32 mmol) of p-octadecylthiobenzonitrile and 94.2 g (0.46 mol) of succinic acid diiso- propyl ester (SAI) are dissolved in 220 g of tert-amyl alcohol at 60C and added over 2 hours to the reaction solution. In the first hour of addition the internal temperature is maintained at 115C but is then slowly reduced to 85C. A further 31. 0 g (0.15 mol) of SAI are then added over 3 hours. Over a further 3 hours, 160 g of an azeotropic mixture of isopropanol and tert- amyl alcohol are then distilled off under reduced pressure (350 mbar) at 85C. The reaction mixture is cooled to room temperature and, over 2.5 hours, added to a mixture of 349 g of ice, 170 g of methanol and 163 g of 60 % sulfuric acid at 0C. During the addition, there are added a further 231 g of MeOH and a total of 1440 g of ice in portions. The resulting mixture is stirred at 0C for 5 hours. The dark-red precipitate is filtered off, washed with 5 litres each of methanol and water and dried at 80C and 200 mbar in a drying cabinet. There are obtai- ned 170 g (88 %) of a red mixture comprising the pigments of formulae (103) and (104), which in PVC results in a transparent red coloration.

Reference： [1]Patent: WO2005/40284,2005,A1 .Location in patent: Page/Page column 32-33
[2]Patent: WO2005/40284,2005,A1 .Location in patent: Page/Page column 34

16
C₁₆H₁₃N₃O [ No CAS ]
[ 924-88-9 ]
C₃₆H₂₈N₆O₄ [ No CAS ]

Reference： [1]Patent: WO2004/7500,2004,A1 .Location in patent: Page/Page column 21-22

17
C₁₇H₁₅N₃O₂ [ No CAS ]
[ 924-88-9 ]
C₃₈H₃₂N₆O₆ [ No CAS ]

Reference： [1]Patent: WO2004/7500,2004,A1 .Location in patent: Page/Page column 17-18

18
C₁₆H₁₃N₃O₂ [ No CAS ]
[ 924-88-9 ]
C₃₆H₂₈N₆O₆ [ No CAS ]

Reference： [1]Patent: WO2004/7500,2004,A1 .Location in patent: Page/Page column 19-20

19
[ 924-88-9 ]
[ 74-88-4 ]
[ 86-53-3 ]
1,4-diketo-2,5-diethyl-3,6-bis(1-naphthyl)pyrrolo[3,4-c]pyrrole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In methanol; tert-Amyl alcohol; dichloromethane; water; N,N-dimethyl-formamide;	Example 54 Synthesis of 1,4-diketo-2,5-diethyl-3,6-bis(1-naphthyl)pyrrolo[3,4-c]pyrrole In 36 mL of t-amyl alcohol, 7.3 g of potassium-t-butoxide were solved, and then log of 1-naphthonitrile were added stirring the solution at 90 C. Into the solution, 6.7 mL of <strong>[924-88-9]diisopropyl succinate</strong> were dropped taking time for 2 hours and were placed under reflux for one day. Next, 30 mL of methanol and 4.4 mL of acetic acid were added at 60 C. and then refluxed for 30 minutes. After cooling, the product was separated out through a filter and subsequently rinsed with methanol, thus resulting in a red powder. Next, 2.89 g of the resulting red powder were dissolved in 80 mL of DMF, and 2.1 g of potassium-t-butoxide were added and stirred for one hour. Then, 1.5 mL of methyl iodide was added and stirred at 65 C. for one day. After 50 mL of water was added, extraction was performed with dichloromethane. The extract was concentrated and refined through a column chromatography with silica gel and thus results in 1.5 g of yellow powder. The following is the results of 1H-NMR analysis. 1H-NMR (CDCl3 (delta=ppm)): 0.93 (tt, 6H), 3.35 (qq, 2H), 3.70 (qq, 2H), 7.58-7.68 (m, 6H), 7.76 (t, 2H), 7.90 (m, 4H), 8.02 (d, 2H)

Reference： [1]Patent: US2003/82406,2003,A1

20
[ 623-03-0 ]
ter-amyl alcohol [ No CAS ]
[ 924-88-9 ]
[ 67-63-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium;	EXAMPLE 1 Co-synthesis of 3,6-di(4-chlorophenyl)-1,4-diketopyrrolo[3,4-c]pyrrole with trans-2,2'-bis(4H-1,4-benzothiazine)-indigo: 60/40 molar-percent A reactor of 1500 ml is charged with 400 ml of ter-amyl alcohol under nitrogen. 50 ml of teramyl alcohol are distilled off the reactor. 18.4 g (0.80 moles) of sodium are added and the mixture is heated to 95-102 C. The molten sodium is then maintained overnight at 100-105 C. with vigorous stirring. To the resulting solution are then added at 60 C., 62.5 g (0.44 moles) of 4-chlorobenzonitrile. Subsequently 58 g (0.286 moles) of <strong>[924-88-9]diisopropyl succinate</strong> are metered in at 96 C. over 2 hours. The resulting isopropanol is distilled off at the same time.
	With sodium;	EXAMPLE 2 Co-synthesis of 3,6-di(4-chlorophenyl)-1,4-diketopyrrolo[3,4-c]pyrrole with 7,7'-dichloro-trans-2,2'-bis(4H-4-benzothiazine)-indigo; 60/40 molar-percent A reactor of 1500 ml is charged with 400 ml of ter-amyl alcohol under nitrogen. 50 ml of teramyl alcohol are distilled off the reactor. 18.4 g (0.80 moles) of sodium are added and the mixture is heated to 95-102 C. The molten sodium is then maintained overnight at 100-105 C. with vigorous stirring. To the resulting solution are then added at 80 C., 62.5 g (0.44 moles) of 4-chlorobenzonitrile. Subsequently 58 g (0.286 moles) of <strong>[924-88-9]diisopropyl succinate</strong> are metered in at 96 C. over 2 hours. The resulting isopropanol is distilled off at the same time.
	With sodium;	EXAMPLE 3 Co-synthesis of 3,6-di(4-chlorophenyl)-1,4-diketopyrrolo[3,4-c]pyrrole with trans-2,2'-bis(4H-1,4-benzothiazine)-indigo: 50/50 by weight A reactor of 1500 ml is charged with 400 ml of ter-amyl alcohol under nitrogen. 50 ml of ter-amyl alcohol are distilled off the reactor. 18.4 g (0.80 moles) of sodium are added and the mixture is heated to 95-102 C. The molten sodium is then maintained overnight at 100-105 C. with vigorous stirring. To the resulting solution are then added at 80 C., 62.5 g (0.44 moles) of 4-chlorobenzonitrile. Subsequently 58 g (0.286 moles) of <strong>[924-88-9]diisopropyl succinate</strong> are metered in at 96 C. over 2 hours. The resulting isopropanol is distilled off at the same time.

Reference： [1]Patent: US6375732,2002,B1
[2]Patent: US6375732,2002,B1
[3]Patent: US6375732,2002,B1

21
[ 924-88-9 ]
[ 21883-13-6 ]
3,6-Bis(2'-methyl-4'-methoxyphenyl)-2,5-dihydropyrrolo(3,4-c)-pyrrole-1,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.82 g (3.86%)	With potassium tert-butylate; In tert-Amyl alcohol;	EXAMPLE 12 3,6-Bis(2'-methyl-4'-methoxyphenyl)-2,5-dihydropyrrolo(3,4-c)-pyrrole-1,4-dione 36.79 g (250 mmol) of <strong>[21883-13-6]2-methyl-4-methoxybenzonitrile</strong> and 28.05 g of potassium tert-butylate in 60 ml of tert-amyl alcohol are reacted with 25.28 g (125 mmol) of diisopropyl succinate in 10 ml of tert-amyl alcohol. Yield 1.82 g (3.86%) of orange powder. Purification is carried out by extractive recrystallisation from toluene by the process described by H. Langhals in Chem. Ber. 118, (1985), 4641. Melting point 319 C. (dec.).=Rf (silica gel/CHCl3)=0.17. UV(DMSO): lambdamax (1 g epsilon)=460 nm (4,405). Fluorescence (DMSO): lambdamax =519 nm. C22 H20 N2 O4 (376.39) Calc.: C, 70.20; H, 5.35; N, 7.44. Found: C, 70.20; H, 5.46; N, 7.24.

Reference： [1]Patent: US5354869,1994,A

22
[ 100-54-9 ]
[ 14906-59-3 ]
[ 924-88-9 ]
[ 7722-84-1 ]
[ 14906-64-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium methylate; sodium; In methanol; tert-Amyl alcohol; water; acetic acid;	The following Examples illustrate the invention. Example 1 6.90 g of sodium are stirred in 120 ml of tert-amyl alcohol at reflux temperature until the reaction is complete. After cooling to 90 C., 24.02 g of 4-cyano-pyridine-N-oxide are added, followed by the dropwise addition of 20.23 g of <strong>[924-88-9]diisopropyl succinate</strong> over 4 hours. The reaction mixture is stirred for 4 hours at 80 C. and then cooled to 30 C. A mixture of 29.56 g of hydrochloric acid and 240 ml of methanol/water (1:2) is run in and stirring is continued for a further 1 hour at room temperature. The precipitated pigment is isolated by filtration, washed with water and extracted hot with methanol. After filtration, the resultant crystals are washed with methanol and water and dried under vacuum, affording 6.80 g (21% of theory) of the compound of formula STR19 in the form of dark-red crystals with a melting point >250 C. Example 2 6.81 g of sodium methylate are stirred in 70 ml of methanol at reflux temperature until the reaction is complete. Then 6.05 g of 4-cyanopyridine-N-oxide are added, followed by the addition in small portions of 9.71 g of the compound of formula STR20 over 2 hours. The mixture is refluxed for 4 hours and then cooled to 40 C. A mixture of 12.4 g of hydrochloric acid and 140 ml of water is added dropwise and stirring is continued for a further 1 hour. The precipitated pigment is isolated by filtration, washed with water and extracted hot with methanol. After filtration, the resultant crystals are washed with methanol and then with water and dried under vacuum at 80 C., affording 3.65 g (28.4 % of theory) of a pigment of formula Example 3A 5.21 g of 3-cyanopyridine are completely dissolved in 50 ml of glacial acetic acid at 40 C., with stirring. Then 9.8 ml of a 30% aqueous solution of H2 O2 are added and the mixture is heated, with stirring, to 100 C. for 2 hours. Thin-layer chromatography shows that the reaction is complete. The solvent is cautiously removed by evaporation and the beige solid is treated with 25 ml of ethanol, cooled and and filtered. The residue is dried at 35 C. under vacuum, affording 3.5 g (58.3% of theory) of 3-cyanopyridine-N-oxide as a white solid with a melting point of 172-174 C.

Reference： [1]Patent: US5502196,1996,A

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 53 The procedure of Example 48 is repeated, except that the mixture is neutralised with 8% by weight hydrochloric acid instead of with glacial acetic acid/methanol. After drying, a yield of 230 g (=66.5% of theory, based on diisopropyl succinate, of pure pigment of the formula VI is obtained.
		EXAMPLE 8 Use of Isopropanol as an Alcohol Example 3 was repeated using 8 g isopropanol in place of tert-butanol, with the addition of 0.3 g of lithium chloride. Reaction time was 2 hours and 13 g of di-isopropyl succinate was formed.

24
[ 1204-85-9 ]
[ 924-88-9 ]
[ 128454-77-3 ]

Reference： [1]Dyes and Pigments,2010,vol. 84,p. 176 - 182

25
[ 924-88-9 ]
[ 1197-19-9 ]
[ 84632-52-0 ]

Reference： [1]Dyes and Pigments,2010,vol. 84,p. 176 - 182

26
[ 623-03-0 ]
[ 924-88-9 ]
[ 2920-38-9 ]
[ 105194-34-1 ]

Yield	Reaction Conditions	Operation in experiment
		Example 1 The first step 200 g tert-amyl alcohol that had been dried over molecular sieve and 140 g sodium tert-amyl alkoxide were introduced under a nitrogen atmosphere into a stainless steel reactor fitted with a reflux condenser and heating to 100C was performed with stirring to produce an alcoholate solution. Separately, 88 g <strong>[924-88-9]diisopropyl succinate</strong>, 97.0 g 4-chlorobenzonitrile, and 3.9 g 4-cyanobiphenyl were introduced into a 500 mL glass flask and were dissolved by heating to 90C with stirring to produce a solution of their mixture. This hot solution of the mixture was gradually added dropwise at a constant rate over 2 hours with vigorous stirring into the above-described alcoholate solution heated to 100C. After the completion of dropwise addition, heating and stirring were continued for 2 hours at 90C to obtain the alkali metal salt of a diketopyrrolopyrrole pigment composition.

Reference： [1]Patent: EP2236562,2010,A1 .Location in patent: Page/Page column 33-34

27
[ 623-03-0 ]
[ 924-88-9 ]
[ 4210-32-6 ]
[ 105261-77-6 ]

Yield	Reaction Conditions	Operation in experiment
		Example 13 A finely divided diketopyrrolopyrrole pigment composition was obtained by performing the same first step and second step as in Example 1, but in this case changing the 97.0 g 4-chlorobenzonitrile and 3.9 g 4-cyanobiphenyl of Example 1 to 95.0 g 4-chlorobenzonitrile and 5.8 g 4-tert-butylbenzonitrile. According to TEM observation, the particles in the resulting finely divided diketopyrrolopyrrole pigment composition were round and had a primary particle diameter of 20 to 40 nm. The yield was 82.5 g.

Reference： [1]Patent: EP2236562,2010,A1 .Location in patent: Page/Page column 42

28
[ 623-03-0 ]
[ 924-88-9 ]
[ 86-53-3 ]
[ 1165778-24-4 ]

Yield	Reaction Conditions	Operation in experiment
		Example 5 A finely divided diketopyrrolopyrrole pigment composition was obtained by performing the same first step and second step as in Example 1, but in this case changing the 97.0 g 4-chlorobenzonitrile and 3.9 g 4-cyanobiphenyl of Example 1 to 74.8 g 4-chlorobenzonitrile and 27.7 g 1-naphthonitrile. According to TEM observation, the particles of the resulting finely divided diketopyrrolopyrrole pigment composition were round and had a primary particle diameter of 20 to 40 nm. The yield was 61.7 g.

Reference： [1]Patent: EP2236562,2010,A1 .Location in patent: Page/Page column 34-35

29
[ 20279-38-3 ]
[ 67-63-0 ]
[ 924-88-9 ]

Yield	Reaction Conditions	Operation in experiment
		[0062] 172 grams of the hydrogenation product from Example 3 and 0.39 gram xylene sulfonic acid catalyst (90% by weight purity) are charged into a 500 ml_ four neck flask equipped with apparatus for distillation, means for feeding isopropanol and thermocouples for sensing mixture temperature and overhead temperature of isopropanol distillate. The mixture is heated up to 110C while wet isopropanol is distilled overhead. Then additional isopropanol is pumped in at a rate of 3.5 grams/minute and wet isopropanol is continuously removed overhead. After 10 hours, the esterification reaction is completed with an acid number of 9.86 milligram KOH/gram sample. The product is purified by vacuum distillation to obtain 98 wt% diisopropyl succinate.

Reference： [1]Patent: WO2011/17543,2011,A1 .Location in patent: Page/Page column 20

30
[ 924-88-9 ]
[ 199531-82-3 ]
[ 1267681-10-6 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 1406 - 1409
[2]Angewandte Chemie - International Edition,2017,vol. 56,p. 10771 - 10774
Angew. Chem.,2017,vol. 129,p. 10911 - 10914,4

31
[ 1003-31-2 ]
[ 924-88-9 ]
3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%		As a specific example embodiment, potassium tert-butoxide (67.4 g, 0.60 mol) and tert-amyl alcohol (400 mL) are added to a nitrogen-protected oven-dried three-neck round-bottom flask equipped with a mechanical stirrer, a thermometer and a reflux condenser. The mixture is heated to 105 C for 1.5 h and to this mixture is added 2- thiophenenitrile (55.2 g, 0.50 mol) and the stirring continued at 105 C for 30 min. A mixture of diisopropyl succinate (40.4 g, 0.20 mol) in tert-amyl alcohol (60 mL) is added dropwise over a period of 3 h with rapid stirring. The mixture is then stirred at 105 C for a further 2 h, then cooled to 50 C, at which point a mixture of methanol (300 mL) and water (80 mL) is added. The reaction mixture is heated at reflux for 45 min before cooling to room temperature. The mixture is poured over 500 g of ice, then concentrated hydrochloric acid (35% aq) (150 mL) and methanol (750 mL) are added and the mixture is stirred for 45 min. The mixture is filtered and the solid is washed with methanol (200 mL). The solid is then suspended in water (1 L) and stirred for 30 min before being filtered again. This suspension in water, stirring and filtration is repeated a further three times. After filtering for the last time, the solid is oven dried at 80 C for 16 h, then dried under vacuum to give the product, 3,6-bis(thiophen-2-yl)- 2H,5H-pyrrolo[3,4-c]pyrrole-l,4-dione, (49.7 g, 82% yield) as a red solid. This compound is used without further purification. 1HNMR (i/s-DMSO, 300 MHz): delta 7.27 (2H, t, J=3.0), 7.89 (2H, dd, J? = 6.0, J2 = 3.0), 8.23 (2H, d, J = 3.0), 11.00 (2H, s); 13CNMR ( DMSO, 75 MHz): delta 1 13.6 (2C), 127.1 (2C), 128.3 (2C), 130.5 (2C), 136.6 (2C), 142.6 (2C), 168.2 (2C); m/z (??) 300.0 [M]+; Anal. Calc. for C14H8 2O2S2: C, 55.98; H, 2.68; N, 9.33 ; S, 21.35.
72%	With iron(III) chloride; sodium; In tert-Amyl alcohol; at 90 - 110℃; for 12h;Inert atmosphere;	Sodium (2 · 30g, lOOmmol),FeCl3 (0 · 20g, 1 · 23mmol) and tert-amyl alcohol (50 mL) was added to a roundbottom flask and the reaction was warmed to 30 minutes at 90 C under N2 atmosphere after after the reaction system was slowly cooled to 50 C, wa added 2-cyano-thiophene (5. 46g, 50mmol), and then heated to 110 C. Then dissolved in 20mL of tert-amyl alcohol diisopropyl succinate (4. 00g, 20mmol)was slowly dripped into the reaction mixture, the reaction for 12 hours. Aftercompletion of the reaction was cooled to 50 C,glacial acetic acid 20mL, refluxed for 30 minutes, cooled to room temperature.Buchner funnel with suction, and the filter cake was washed with methanol untilthe filtrate was extracted presentation was colorless, dark purple solid wasobtained (of formula (5) Compound 5) 6. 88g, 72% yield. Product was usedwithout purification in the next reaction directly.
59%		Sodium (~1.3 equiv., 7.2g, 313.2mmol) was dissolved in tert-amyl alcohol (400mL) heated to reflux and with the addition of catalytic amount of iron(III) chloride. After dissolution of all sodium, there was added in one portion 1.0 equiv. of <strong>[1003-31-2]thiophene-2-carbonitrile</strong> (26.2g, 240.0mmol) and the reaction mixture was stirred for 30minat reflux. Then, 0.65 equiv. of diisopropyl succinate (31.6g, 156.2mmol) dissolved in tert-amyl alcohol (80mL) was gradually added dropwise for 4h and the mixture was stirred at reflux for 18h. After that, protolysis was performed by addition of diluted acetic acid to the reaction mixture cooled to laboratory temperature. The mixture was refluxed for 6h and then the heterogenic mixture was filtered while hot and the filter cake was washed with hot water and isopropyl alcohol. The crude product was refluxed in methanol for 1h and, after that, it was filtered while hot to get a pure product. (0014) Th-DPP: Dark purple solid (27.5g, yield 59%). Melting point >400C, 1H NMR (300MHz, DMSO-d6, ppm): delta=11.21 (s, 2H), 8.20 (d, J=3.01Hz, 2H), 7.93 (d, J=3.04Hz, 2H), 7.31-7.27 (m, 2H), Anal. calcd. for C14H8N2O2S2: C 55.98%, H 2.68%, N 9.33%, Found: C 55.42%, H 2.37%, N 9.71%.

50.8%		Charge a 200-ml four-neck flask with t-l3uOK (19 g, 170 mmol) and t-amyl alcohol (70 ml) and heat to reflux under agitation.Gradually drop a mixture of <strong>[1003-31-2]2-cyanothiophene</strong> (10.9 g, 100 mmol) and diisopropyl succinate (9.63 g, 47.6 mmol) in the flask. After 3 hours of reflux, cool the flask content to 70 C. and add acetic acid (20 ml) and MeOR (20 ml) to theflask. After cooling to room temperature, filter the flaskcontent with a glass filter to separate the precipitate. Washthe filter residue with methanol for 3 times and then dry it in a vacuum drier. Thus, a red solid (12.1 g, 42.2 mmol) represented by the formula (a) is prepared (at a yield of50.8%). mlz=301.01 (M+H)
50.8%	With potassium tert-butylate; In tert-Amyl alcohol; for 3h;Reflux;	19 g (170 mmol) of t-BuOK and 70 mK of t-amylalcohol were placed in a 200 mL four-necked flask and heated under reflux with stirring. Next, a mixture of 10.9 g (100 mmol) of <strong>[1003-31-2]2-cyanothiophene</strong> and 9.63 g (47.6 mmol) of diisopropylsuccinate was gradually added dropwise, followed by refluxing for 3 hours. After further cooling to 70 C., 20 mL of acetic acid and 20 mL of MeOH were added. Next, after cooling to room temperature, the formed precipitate was collected by filtration using a glass filter. Further, the filtrate was washed three times with methanol and then dried using a vacuum dryer to obtain 12.1 g (yield: 50.8%) of the compound represented by the chemical formula (2-1) which is a red solid, Was obtained. The compound represented by the chemical formula (2-1) had m / z of 301.01 ([M+H]+)
	With hydrogenchloride; potassium tert-butylate; In methanol; tert-Amyl alcohol; water;	Thiophene-carbonitrile and diisopropyl succinate are combined to form a thiophene substituted DPP. This is done in tert-amyl alcohol, with a yield of 82%. The basic thienyl DPP is then N-alkylated using a straight chain alkyl bromide (88% yield), followed by alpha-bromination of the thiophene groups (90% yield) to make it suitable as a Stille coupling co-monomer. The final material (bromothienyl-DC17DPP) is purified by recrystallization from chloroform giving a 65% overall yield for the three steps. As a specific example embodiment, potassium tert-butoxide (67.4 g, 0.60 mol) and tert-amyl alcohol (400 mL) are added to a nitrogen-protected oven-dried three-neck round-bottom flask equipped with a mechanical stirrer, a thermometer and a reflux condenser. The mixture is heated to 105 C. for 1.5 h and to this mixture is added 2-thiophenenitrile (55.2 g, 0.50 mol) and the stirring continued at 105 C. for 30 min. A mixture of diisopropyl succinate (40.4 g, 0.20 mol) in tert-amyl alcohol (60 mL) is added dropwise over a period of 3 h with rapid stirring. The mixture is then stirred at 105 C. for a further 2 h, then cooled to 50 C., at which point a mixture of methanol (300 mL) and water (80 mL) is added. The reaction mixture is heated at reflux for 45 min before cooling to room temperature. The mixture is poured over 500 g of ice, then concentrated hydrochloric acid (35% aq) (150 mL) and methanol (750 mL) are added and the mixture is stirred for 45 min. The mixture is filtered and the solid is washed with methanol (200 mL). The solid is then suspended in water (1 L) and stirred for 30 min before being filtered again. This suspension in water, stirring and filtration is repeated a further three times. After filtering for the last time, the solid is oven dried at 80 C. for 16 h, then dried under vacuum to give the product, 3,6-bis(thiophen-2-yl)-2H,5H-pyrrolo[3,4-c]pyrrole-1,4-dione, (49.7 g, 82% yield) as a red solid. This compound is used without further purification. 1HNMR (d6-DMSO, 300 MHz): delta 7.27 (2H, t, J=3.0), 7.89 (2H, dd, J1=6.0, J2=3.0), 8.23 (2H, d, J=3.0), 11.00 (2H, s); 13CNMR (d6-DMSO, 75 MHz): delta 113.6 (2C), 127.1 (2C), 128.3 (2C), 130.5 (2C), 136.6 (2C), 142.6 (2C), 168.2 (2C); m/z (EI+) 300.0 [M]+; Anal. Calc. for C14H8N2O2S2: C, 55.98; H, 2.68; N, 9.33; S, 21.35.
	With iron(III) chloride; sodium; In tert-Amyl alcohol; at 105℃; for 4h;	4 g of sodium metal granules were added to a three-necked flask containing 100 mL of tert-amyl alcohol.20mg of ferric chloride was added to tert-amyl alcohol, and the oil was reacted at 110 C for 2 hours, and cooled to 60 C., adding 7.5 g of <strong>[1003-31-2]2-cyanothiophene</strong>, and starting to raise the temperature to 105 C,At the same time, 7.2 mL of diisopropyl succinate was added dropwise, and the mixture was dripped in three hours.After the completion of the dropwise addition, the reaction was carried out at 105 C for 4 hours, then the temperature was lowered to room temperature, and acetic acid was added to neutrality.The solid was obtained by suction filtration, washed three times with methanol and three times with deionized water.Drying gives 3,6-bis(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione. )(3g, 10mmol), 1,6-dibromohexane (9.76g, 40mmol),Potassium tert-butoxide (4.49 g, 40 mmol) and solvent acetonitrile 30 mL were placed in a 150 mL pressure-resistant bottle, mixed with heating and refluxed for 8 h, and suction filtered with a suction filter.The obtained filtrate was evaporated to remove the solvent to give a crude material.Petroleum ether = 1:1 as a developing solvent gave solid compound A-1 4.16 g, yield 70%.

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 9101 - 9110
[2]New Journal of Chemistry,2019,vol. 43,p. 2274 - 2277
[3]Journal of the American Chemical Society,2011,vol. 133,p. 2198 - 2204
[4]Chemistry of Materials,2013,vol. 25,p. 782 - 789
[5]Patent: WO2013/66732,2013,A1 .Location in patent: Paragraph 00172
[6]Patent: CN103360397,2016,B .Location in patent: Paragraph 0031-0034
[7]RSC Advances,2014,vol. 4,p. 58027 - 58035
[8]Dyes and Pigments,2020,vol. 175
[9]Patent: US9590187,2017,B2 .Location in patent: Page/Page column 38; 39
[10]Patent: JP6236813,2017,B2 .Location in patent: Paragraph 0167; 0168
[11]Patent: US2013/109821,2013,A1 .Location in patent: Page/Page column
[12]Dyes and Pigments,2014,vol. 100,p. 118 - 126
[13]Organic Letters,2015,vol. 17,p. 394 - 394
[14]Patent: CN109824674,2019,A .Location in patent: Paragraph 0062-0064

32
[ 40985-58-8 ]
[ 924-88-9 ]
[ 1246679-11-7 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 3272 - 3275

33
[ 924-88-9 ]
4-(3-((-t-butyldimethylsilyl)oxy)propoxy)benzonitrile [ No CAS ]
3,6-bis(4-(3-((-t-butyldimethylsilyl)oxy)propoxy)phenyl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione [ No CAS ]

Reference： [1]Heterocyclic Communications,2010,vol. 16,p. 213 - 216

34
[ 924-88-9 ]
[ 455-18-5 ]
[ 88949-31-9 ]

Yield	Reaction Conditions	Operation in experiment
81%	With iron(III) chloride; sodium; In tert-Amyl alcohol; at 100℃; for 3h;Inert atmosphere;	Take a 250 mL three-necked flask and add 100 mL of dry tert-amyl alcohol.Sodium (4.0 g, 100 mmol), 10 mg of ferric chloride, heated to 100 C,The mixture was heated and stirred under a nitrogen atmosphere for about 30 minutes, and the sodium particles were completely dissolved. Cool down to around 50 CThen, 4-trifluoromethylbenzonitrile, Compound 1-1 (11.8 g, 68.6 mmol) was added to the system, and the temperature was raised to 100 C. Diisopropyl succinate, Compound 2 (8 mL, 39.6 mmol), was diluted with 30 mL of tert-amyl alcohol, and the mixture was slowly dropped (2-3 h) into a three-necked flask using a constant pressure dropping funnel. After the addition was completed, the reaction was continued for 3 hours.After the reaction is completed, the reaction mixture is poured into a clean 500 mL beaker and naturally cooled to room temperature. Slowly add glacial acetic acid to the beaker to adjust the pH to neutrality.Out. Filter through a Buchner funnel and wash the filter cake with methanol and water until the filtrate is colorless and transparent.After drying the filter cake, a brick red solid powder, Compound 3-1, is obtained.The yield was 81%.
51%	With iron(III) chloride; sodium tert-pentoxide; at 50 - 120℃;	General procedure: A mixture of sodium (2.30 g, 100 mmol), t-amyl alcohol (50 mL) and catalytic amount of FeCl3 were added into a three-necked flask under air. After being stirred vigorously at 100 C for 1 h, the mixture was cooled to 50 C, 3 (40 mmol) was added. Then the mixture was heated to 100 C, <strong>[924-88-9]diisopropyl succinate</strong> (4.00 g, 40 mmol) in t-amyl alcohol (20 mL) was added dropwise over 2 h. Subsequently, the resulting suspension was kept for 3 h at 120 C, and cooled to room temperature. Glacial acetic acid was slowly added till pH was 7.0, followed by methanol and water (1:2, v:v,100 mL) added, the mixture was heated under reflux for 2 h. After cooling filtration and dried, the corresponding product was obtained. The product (2) was used without further purification.
	With iron(III) chloride; sodium; In tert-Amyl alcohol; at 100 - 105℃;	100 ml of tert-amyl alcohol was placed in a 250 ml three-necked flask, and 4 g of sodium was cut into sodium pellets, and then acatalytic amount of 20-40 mg of ferric chloride was added as a catalyst. Heat to 100 ~ 105 C, the reaction 2 ~ 3h. Thetemperature was lowered to 50 to 60 C, and 68.6 mmol of the compound 2-5 was added, followed by heating to 100 to 105 C.8 ml of a mixture of <strong>[924-88-9]diisopropyl succinate</strong> compound 1 and 40 ml of tert-amyl alcohol was added to a three-necked flask througha constant pressure dropping funnel, and the mixture was 3-5 hours after 2-3 hours. Finally, react for another 4 hours, stop thereaction, pour the reaction product into a beaker, dilute with 100 ml of methanol, add acetic acid to adjust the pH to 7, filter withsuction, wash the filter cake with methanol, take the filter cake, heat and dry, then use N, The N-dimethylformamide is thermallydissolved, cooled and suction filtered, and the filter cake is washed with water and methanol, and the filter cake is taken anddried by heating to obtain the product 3-5.

Reference： [1]Patent: CN109897045,2019,A .Location in patent: Paragraph 0051-0053
[2]Tetrahedron,2017,vol. 73,p. 494 - 499
[3]Chemistry Letters,2011,vol. 40,p. 822 - 824
[4]Patent: CN109897043,2019,A .Location in patent: Paragraph 0107; 0109-0111

35
[ 924-88-9 ]
[ 200358-06-1 ]
[ 1371538-16-7 ]

Reference： [1]Chemistry Letters,2011,vol. 40,p. 822 - 824

36
[ 66739-89-7 ]
[ 924-88-9 ]
3,6-bis(4-(1,3-dioxolan-2-yl)phenyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With sodium; In tert-Amyl alcohol; at 100℃;Inert atmosphere;	Sodium (4.00g, 174mmol) was added in t-amyl alcohol (100mL) at 50C, the mixture was heated to 100C until the sodium disappeared completely. Then the solution was cooled to 50C, 4-(1,3-dioxolan-2-yl) benzonitrile (13.8g, 78.86mmol) was added, <strong>[924-88-9]diisopropyl succinate</strong> (8.07mL, 39.43mmol) in t-amyl alcohol (30mL) was added dropwise under the protection of an argon atmosphere. Subsequently, the resulting suspension was stirred at 100C overnight, and cooled to room temperature. The mixture was poured into a mixture of hydrochloric acid and methanol. The precipitate was filtered and washed with water and methanol, dark-red solid was obtained after dried under vacuum (5.96g, 35%). The product was used without further purification.
	With iron(III) chloride; sodium; In tert-Amyl alcohol; at 90 - 120℃; for 5h;	Sodium (2.30g, 100mmol) was dissolved in t-amyl alcohol (50mL) at 90C over 1h with catalytic amount of FeCl3, then the solution was cooled to 50C, 4-(1,3-dioxolan-2-yl)benzonitrile (7.00g, 40mmol) was added. The mixture was heated to 90C, <strong>[924-88-9]diisopropyl succinate</strong> (4.00g, 40mmol) in t-amyl alcohol (20mL) was added over 2h. Subsequently, the resulting suspension was kept for 3hat 120C, and cooled to room temperature. Glacial acetic acid was slowly added till pH was 7.0, after methanol and water (1/2, 100mL) added, the mixture was refluxed for 2h. After filtration and drying, bluish-red solid was obtained (4.00g, 30%). The product was used without further purification.
	With iron(III) chloride; sodium; In tert-Amyl alcohol; at 110℃; for 4h;	Add 30 mL of tert-amyl alcohol to a three-necked flask,Add 4g of sodium granules under stirring,Add a catalytic amount of 5mg of ferric chloride, raise the temperature to 110 C and keep it for 2 hours.Cool the mixture to room temperature, add Compound 1 (13g, 0.074mol),The temperature was raised to 110 C, and then a solution of <strong>[924-88-9]diisopropyl succinate</strong> (7.5 g, 0.037 mol) in tert-amyl alcohol (30 mL) was added dropwise. The dropping speed was maintained at 3 to 4 seconds per drop, and the reaction was continued after the drop was completed. After dripping, the reaction was continued for another 4 hours,After the reaction is completed, cool the reaction solution to room temperature, add acetic acid to adjust the pH to neutral, suction filter,drying. Reflux the solid crude product with water, suction filtration, and drying;The solid crude product was refluxed with N, N-dimethylformamide, suction filtered, and dried.The cycle was repeated twice to obtain red solid compound 2.

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 9294 - 9304
[2]Journal of Photochemistry and Photobiology A: Chemistry,2017,vol. 346,p. 265 - 272
[3]Journal of Materials Chemistry C,2018,vol. 6,p. 1377 - 1383
[4]Journal of Fluorescence,2014,vol. 24,p. 1347 - 1355
[5]Journal of Materials Chemistry C,2015,vol. 3,p. 6876 - 6881
[6]New Journal of Chemistry,2015,vol. 39,p. 7211 - 7218
[7]RSC Advances,2016,vol. 6,p. 55182 - 55193
[8]Dyes and Pigments,2016,vol. 134,p. 586 - 592
[9]RSC Advances,2016,vol. 6,p. 96676 - 96685
[10]Journal of Fluorescence,2017,vol. 27,p. 1 - 8
[11]New Journal of Chemistry,2017,vol. 41,p. 3367 - 3373
[12]Patent: CN110590784,2019,A .Location in patent: Paragraph 0050; 0053-0054

37
[ 623-26-7 ]
[ 924-88-9 ]
[ 84632-51-9 ]

Reference： [1]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 3427 - 3430

38
[ 617-90-3 ]
[ 924-88-9 ]
3,6-bis(furan-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrolo-1,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Under nitrogen atmosphere,In 125 parts of tert-amyl alcohol,While stirring, 4.28 parts of sodium hydride (60%) are added.Furthermore, 10 parts of 2-cyanofuran,9.71 parts of <strong>[924-88-9]diisopropyl succinate</strong>tert-amyl alcoholDissolved in 9 parts,Was added.Heat up to 100 C,Stir for 4 hours. It is then cooled to 60 C. and at this temperature acetic acid 12. A mixture of 6 parts and 180 parts of methanol was added dropwise,After dropping,Heating was applied for 0.5 hour at 60 C.It is then filtered, washed with methanol and dried at 60 C. to give a dark red powder. 88 parts were obtained.

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 9101 - 9110
[2]Journal of Materials Chemistry,2012,vol. 22,p. 4425 - 4435
[3]RSC Advances,2015,vol. 5,p. 84643 - 84656
[4]Chemical Communications,2012,vol. 48,p. 8383 - 8385
[5]Journal of Materials Chemistry,2012,vol. 22,p. 17284 - 17292
[6]Patent: JP2020/23676,2020,A .Location in patent: Paragraph 0073

39
[ 1641-09-4 ]
[ 924-88-9 ]
[ 88949-35-3 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2670 - 2673
[2]Organic Letters,2015,vol. 17,p. 394 - 394

40
[ 924-88-9 ]
[ 405549-76-0 ]
[ 1375421-27-4 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2670 - 2673
[2]Organic Letters,2015,vol. 17,p. 394 - 394

41
[ 924-88-9 ]
[ 1283853-17-7 ]
[ 1375421-28-5 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2670 - 2673
[2]Chemistry - A European Journal,2014,vol. 20,p. 12493 - 12501
[3]Organic Letters,2015,vol. 17,p. 394 - 394

42
[ 924-88-9 ]
[ 1375421-26-3 ]
[ 1375421-29-6 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2670 - 2673
[2]Organic Letters,2015,vol. 17,p. 394 - 394

43
[ 2024-83-1 ]
[ 924-88-9 ]
[ 84632-45-1 ]

Yield	Reaction Conditions	Operation in experiment
	With iron(III) chloride; tert-Amyl alcohol; sodium; at 90 - 110℃; for 16.5h;	A three-necked flask equipped with a reflux condenser and magnetic stirrer was charged with 40 ml of ferf-amyl alcohol, 1.15 g of sodium (50 mmol) and a catalytic amount of iron(lll) chloride. The mixture was heated at the boiling point until the sodium had reacted completely. Then the reaction mixture was cooled to 90C and 23 mmol of nitrile was added with a syringe (solid nitriles should be dissolved beforehand in a small amount of ferf- amyl alcohol). The mixture was heated to 110C and 2.1 ml (10 mmol) of <strong>[924-88-9]diisopropyl succinate</strong> was added dropwise in the space of 30 min. After reaction at 110C for 16 h, the flask contents were cooled and 100 ml of a mixture of water, methanol and acetic acid in volumetric proportions 1 :1 :1 was added. The suspension obtained was heated for some minutes at the boiling point and then cooled to 30C. The precipitate was filtered off, washed several times with hot water and methanol and dried under reduced pressure.; 2.1 1 ,4-Diketo-3,6-di(3,4-dimethoxyphenyl)pyrrolo[3,4-c]pyrrole (1a): Obtained from 3,4-dimethoxybenzonitrile (0a) (3.75 g, 23 mmol). Yield: 736 mg (18%). Red powder. M.p.: Decomposition>370C. 1H-NMR (500 MHz, DMSO-de, 80C): delta 10.84 (s, 2H), 8.18 (d, J= 2.0 Hz, 2H), 8.10 (dd, Ji = 2.0 Hz, J2 = 8.4 Hz, 2H), 7.1 1 (d, J= 8.4 Hz, 2H), 3.88 (s, 6H)), 3.86 (s, 6H). 13C-NMR (125 MHz, DMSO-de): delta 163.0, 152.5, 149.7, 143.7, 122.4, 121.5, 112.8, 112.4, 109.9, 56.5, 56.4. HRMS (El 70 eV) calc. for C22H20N2O6 (M+): 408.1321 , found: 408.1316. Calc. elem. anal. (%) for the formula C22H20N2O6: C 64.70, H 4.94, N 6.86; found: C 64.64, H 4.99, N 6.62.

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 12493 - 12501
[2]Organic Letters,2012,vol. 14,p. 2670 - 2673
[3]Organic Letters,2015,vol. 17,p. 394 - 394
[4]Patent: WO2013/92474,2013,A1 .Location in patent: Page/Page column 42; 43

44
[ 924-88-9 ]
[ 428865-55-8 ]
3,6-bis(7-bromo-9,9-dioctyl-9H-fluoren-2-yl)-1,4-diketopyrrolo[3,4-c]pyrrole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23.7%	With iron(III) chloride; sodium; In tert-Amyl alcohol; at 110℃;Inert atmosphere;	b) Reaction flask (250 mL) is charged with 40 ml 2-methyl-2-butanol, 2.0 g (86.9 mmol) sodium, and 30 mg iron(lll)chloride under argon. The reaction mixture is heated to 100C under argon. The reaction mixture is stirred 1 h to the moment when all sodium is dissolved. Then the reaction mixture is cooled to 90C and 7-bromo-9,9-dioctyl-9/-/-fluorene-2- carbonitrile (10.14 g, 20.5 mmol) is added in one portion (wash with 20 ml of 2-methyl-2- butanol). The reaction is stirred for 10 minutes, warmed up to 110C and 1.98 g (9.79 mmol) <strong>[924-88-9]diisopropyl succinate</strong> is added via syringe. The reaction mixture is stirred in an oil bath at 110C under argon overnight. Next day the reaction mixture is cooled to 60C, quenched by addition of 25 mL AcOH, 25 mL water and 25 mL EtOH. After 1 h at 100C the stirring is continued overnight at RT. Next day 100 mL of water are added and the raw product is filtered on G3 filter. To the residue filter cake water (25 mL) and EtOH (600 mL) are added in small portions, then the product is isolated by filtration and dried at room temperature under vacuum (oil pump). Yield 2.49 g (23.7 %) of a compound of formula 15. This compound is directly used in the next reaction to give compound 16.

Reference： [1]Patent: WO2014/206863,2014,A1 .Location in patent: Page/Page column 80

45
[ 924-88-9 ]
7-bromo-9,9-di(2-methoxyethyl)-9H-fluorene-2-carbonitrile [ No CAS ]
3,6-bis(7-bromo-9,9-di(2-methoxyethyl)-9H-fluoren-2-yl)-1,4-diketopyrrolo[3,4-c]pyrrole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With iron(III) chloride; sodium; In tert-Amyl alcohol; at 110℃; for 16h;Inert atmosphere;	c) 3,6-Bis(7-bromo-9,9-di(2-methoxyethyl)-9/-/-fluoren-2-yl)-1 ,4-diketopyrrolo[3,4-c]pyrrole 4: Under an argon atmosphere, in a three-necked flask equipped with a reflux condenser and magnetic stirrer are placed 20 ml of ferf-amyl alcohol, an catalytic amount of iron(lll) chloride and sodium (0.690 g, 30 mmol). The mixture is heated under reflux until sodium is completely reacted. Then the reaction mixture is cooled to 90 C and 7-bromo-9,9-di(2- methoxyethyl)-9H-fluorene-2-carbonitrile (2, 4.87 g, 12.6 mmol) is added. The mixture is then heated to 110 C and 1.23 ml (6.0 mmol) of <strong>[924-88-9]diisopropyl succinate</strong> 3 is added dropwise (30 min). After 16 h of reaction at 110 C, the mixture is cooled and 30 ml of water/acetic acid 1 : 1 is added. Resulting suspension is refluxed for a few minutes and cooled to 30 C. Precipitate of obtained pigment is then filtered out, washed several times with hot water and methanol and dried under vacuum. 1.66 g (32%) of 4 is obtained as dark brown powder. Mp: >400 C. H NMR (500 MHz, CDCb : TFA-d 4 : 1) 5 8.48 (br s, 2H), 8.22 (br s, 2H), 7.96 (br s, 2H), 7.72 (d, J = 8.0 Hz, 2H), 7.69 - 7.62 (m, 4H), 3.17 (s, 6H), 3.11 - 2.95 (m, 8H), 2.59 (br s, 4H), 2.50 (br s, 4H). HRMS (ESI) calcd for C44H42Br2N206Na (M+Na+): 875.1301 , found: 875.1307.

Reference： [1]Patent: WO2014/206863,2014,A1 .Location in patent: Page/Page column 75; 76

46
[ 164352-20-9 ]
[ 924-88-9 ]
[ 1190375-39-3 ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 2893 - 2904

47
[ 924-88-9 ]
[ 108656-24-2 ]
C₃₀H₃₀N₄O₄ [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2015,vol. 3,p. 742 - 749

48
[ 924-88-9 ]
[ 874-90-8 ]
[ 104616-31-1 ]

Yield	Reaction Conditions	Operation in experiment
15%		General procedure: Under nitrogen condition, potassium tert-butoxide (2.25 g, 0.02 mol) was dissolved in150 mL of tert-amyl alcohol for 15 min and the mixture was heated to 110. Iron(III) chloride (s.a) was added and stirred for 30 min then 4-chlorobenzonitrile (1.5 g, 0.01 mol) was added and stirred for 1 hr at the same temperature. Diisopropyl succinate (1.01g, 0.005 mol) was dissolved in 30 mL of tert-amyl alcohol and dropwised to the mixture for 3 hr. Then 60 mL of water was poured into mixture and stirred for 20 hr at the same temperature. After reaction, the mixture was cooled to room temperature. The mixture was filtered off and washed by water, methanol. The red pigment was purified by 50 mL methanol and stirred for 30 min at 60. After stirring, the solution was filtered off and dried under vacuum to obtain Pigment.

Reference： [1]Molecular Crystals and Liquid Crystals,2015,vol. 617,p. 73 - 81

49
4-(1-methyl-1H-pyrrol-2-yl)benzonitrile [ No CAS ]
[ 924-88-9 ]
C₂₈H₂₂N₄O₂ [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2016,vol. 4,p. 2877 - 2885

50
[ 75-85-4 ]
[ 924-88-9 ]
[ 3939-14-8 ]
C₂₆H₃₀N₄O₄ [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2016,vol. 4,p. 2877 - 2885

51
[ 1620-75-3 ]
[ 924-88-9 ]
C₁₈H₁₄N₄O₂ [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2016,vol. 4,p. 2877 - 2885

52
[ 924-88-9 ]
[ 127680-91-5 ]
C₂₄H₂₄N₆O₄ [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2016,vol. 4,p. 2877 - 2885

53
[ 924-88-9 ]
6-(4-hexylthiophen-2-yl)nicotinonitrile [ No CAS ]
3,6-bis(6-(4-hexylthiophen-2-yl)pyridin-3-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2016,vol. 4,p. 2470 - 2479

54
[ 924-88-9 ]
7-bromo-9,9-di(2-methoxyethyl)-9H-fluorene-2-carbonitrile [ No CAS ]
3,6-bis(7-bromo-9,9-di(2-methoxyethyl)-9H-fluoren-2-yl)-1,4-diketopyrrolo[3,4-c]pyrrole [ No CAS ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 12493 - 12501

55
[ 924-88-9 ]
[ 428865-55-8 ]
3,6-bis(7-bromo-9,9-dioctyl-9H-fluoren-2-yl)-1,4-diketopyrrolo[3,4-c]pyrrole [ No CAS ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 12493 - 12501

56
[ 924-88-9 ]
[ 1190198-24-3 ]
3,6-bis(6-bromobenzo[b]thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 83448 - 83455

57
[ 38251-66-0 ]
[ 924-88-9 ]
3,6-bis(5-bromobenzo[b]thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 83448 - 83455

58
[ 924-88-9 ]
[ 88374-55-4 ]
[ 944330-98-7 ]

Yield	Reaction Conditions	Operation in experiment
32%	With potassium tert-butylate; In tert-Amyl alcohol; for 9h;Inert atmosphere; Reflux;	Next, under an argon stream, tert-butyloxy potassium (25.18 g, 224.4 mmol) and 160 mL of tert-amyl alcohol were put into a 500 mL four-neck flask, and a solution obtained by mixing the compound (b-1) (14.8 g, 64 mmol) synthesized above and 7 mL of tert-amyl alcohol was added thereto. While heating to reflux, a solution obtained by mixing <strong>[924-88-9]succinic acid diisopropyl ester</strong> (6.5 g, 32 mmol) and 10 mL of tert-amyl alcohol was added dropwise thereto over a period of about 3 hours, and after dropping ended, the resultant product was heated to reflux for 6 hours. After the temperature was returned to room temperature, the obtained reaction liquid having high viscosity was put into a solution of acetic acid:methanol:water=1:1:1, and the resultant product was heated to reflux for several minutes, whereby a red solid precipitated. The solid was separated by filtration, and washed with heated methanol and water, whereby 3,6-(4-octyloxyphenyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (b-2) was obtained as a red solid (obtained amount: 5.6 g, yield: 32%).
30%	With potassium tert-butylate; In tert-Amyl alcohol; at 110℃; for 6h;	Potassium tert-butoxide (1.68 g, 15 mmol) was added to 2-methyl-2 -butanol (15 mL), and the mixture was heated to reflux. When the base had dissolved, 4- (octyloxy)benzonitrile (2.3 g, 10 mmol) was added in one portion. Then <strong>[924-88-9]diisopropyl succinate</strong> (1.01 g, 5 mmol) was added over 3 h with a dropping funnel. After heating for another 3 h at 110 C, the mixture was cooled and slowly added to a mixture of 100 mL of ethanol with 2 mL of concentrated hydrochloric acid. The red precipitate was collected by filtration and washed with ethanol. The solid was digested in boiling ethanol, collected by filtration and washed with ethanol. This procedure was repeated until the filtrate was clear. Drying in vacuum yielded an orange solid 1.6 g (Yield, 30 %).

Reference： [1]Patent: US2016/271273,2016,A1 .Location in patent: Paragraph 0273
[2]Patent: WO2020/60937,2020,A1 .Location in patent: Page/Page column 180

59
[ 924-88-9 ]
[ 92371-47-6 ]

Yield	Reaction Conditions	Operation in experiment
	With 5%-palladium/activated carbon; hydrogen; In isopropyl alcohol; at 180℃; under 22502.3 Torr;Autoclave;	0.1 g of a Pt / C catalyst with a reduced loading of 5 wt.%, 0.1 g of tungstophosphoric heteropoly acid and 20 mL of isopropanol were charged into a 50 mL autoclave, After sealing, the inside of the reaction vessel was replaced with hydrogen 6 times.And then filled with 3MPa hydrogen, heated to 180 C stirring to maintain a certain reaction time, and then cooled to room temperature, stop stirring, carefully depressurize to normal pressure.After filtering off the catalyst, the whole product was transferred to a 25 mL volumetric flask and the internal standard was added and the solvent was used to make the volume.Analysis of the product according to the procedure in Example 2 gave the conversion of <strong>[924-88-9]diisopropyl succinate</strong> and the selectivity of diisopropyl 1,4-cyclohexanedicarboxylate as shown in Fig.

Reference： [1]Patent: CN104276953,2016,B .Location in patent: Paragraph 0043 - 0045

60
[ 924-88-9 ]
[ 3058-39-7 ]
3,6-bis(4-iodophenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With iron(III) chloride; sodium tert-pentoxide; at 50 - 120℃;	General procedure: A mixture of sodium (2.30 g, 100 mmol), t-amyl alcohol (50 mL) and catalytic amount of FeCl3 were added into a three-necked flask under air. After being stirred vigorously at 100 C for 1 h, the mixture was cooled to 50 C, 3 (40 mmol) was added. Then the mixture was heated to 100 C, <strong>[924-88-9]diisopropyl succinate</strong> (4.00 g, 40 mmol) in t-amyl alcohol (20 mL) was added dropwise over 2 h. Subsequently, the resulting suspension was kept for 3 h at 120 C, and cooled to room temperature. Glacial acetic acid was slowly added till pH was 7.0, followed by methanol and water (1:2, v:v,100 mL) added, the mixture was heated under reflux for 2 h. After cooling filtration and dried, the corresponding product was obtained. The product (2) was used without further purification.

Reference： [1]Tetrahedron,2017,vol. 73,p. 494 - 499

61
[ 924-88-9 ]
[ 104-85-8 ]
[ 84632-66-6 ]

Yield	Reaction Conditions	Operation in experiment
36%	With iron(III) chloride; sodium tert-pentoxide; at 50 - 120℃;	General procedure: A mixture of sodium (2.30 g, 100 mmol), t-amyl alcohol (50 mL) and catalytic amount of FeCl3 were added into a three-necked flask under air. After being stirred vigorously at 100 C for 1 h, the mixture was cooled to 50 C, 3 (40 mmol) was added. Then the mixture was heated to 100 C, <strong>[924-88-9]diisopropyl succinate</strong> (4.00 g, 40 mmol) in t-amyl alcohol (20 mL) was added dropwise over 2 h. Subsequently, the resulting suspension was kept for 3 h at 120 C, and cooled to room temperature. Glacial acetic acid was slowly added till pH was 7.0, followed by methanol and water (1:2, v:v,100 mL) added, the mixture was heated under reflux for 2 h. After cooling filtration and dried, the corresponding product was obtained. The product (2) was used without further purification.

Reference： [1]Tetrahedron,2017,vol. 73,p. 494 - 499

62
[ 924-88-9 ]
[ 1194-02-1 ]
[ 84632-57-5 ]

Yield	Reaction Conditions	Operation in experiment
60%	With iron(III) chloride; sodium tert-pentoxide; at 50 - 120℃;	General procedure: A mixture of sodium (2.30 g, 100 mmol), t-amyl alcohol (50 mL) and catalytic amount of FeCl3 were added into a three-necked flask under air. After being stirred vigorously at 100 C for 1 h, the mixture was cooled to 50 C, 3 (40 mmol) was added. Then the mixture was heated to 100 C, <strong>[924-88-9]diisopropyl succinate</strong> (4.00 g, 40 mmol) in t-amyl alcohol (20 mL) was added dropwise over 2 h. Subsequently, the resulting suspension was kept for 3 h at 120 C, and cooled to room temperature. Glacial acetic acid was slowly added till pH was 7.0, followed by methanol and water (1:2, v:v,100 mL) added, the mixture was heated under reflux for 2 h. After cooling filtration and dried, the corresponding product was obtained. The product (2) was used without further purification.
	With iron(III) chloride; sodium; In tert-Amyl alcohol; at 100 - 105℃;	100 ml of tert-amyl alcohol was placed in a 250 ml three-necked flask, 4 g of sodium was cut into sodium pellets and added to it. A catalytic amount of 20-40 mg of ferric chloride was added as a catalyst, heated to 100 ~ 105 C, and reacted for 2 ~ 3h. The temperature was lowered to 50 to 60 C, and 68.6 mmol of the compound 2-2 was added and heated to 100 to105 C. 8 ml of a mixture of <strong>[924-88-9]diisopropyl succinate</strong> compound 1 and 40 ml of tert-amyl alcohol was added to a three-necked flask using a constant pressure dropping funnel, 3-5 s/d for 2-3 hours. Finally, the reaction mixture was reacted for another 4 hours, the reaction was stopped, the reaction product was poured into a beaker, diluted with 100 ml of methanol, acetic acid was added to adjust the pH to 7, suction filtered, the filter cake was washed with methanol, the filter cake was removed, heated, dried, heated with N,N-dimethylformamide, cooled, suction-filtered, filter cake was washed sequentially with water and methanol and the filter cake was dried by heating to obtain the product 3-2.

Reference： [1]Tetrahedron,2017,vol. 73,p. 494 - 499
[2]Patent: CN109897043,2019,A .Location in patent: Paragraph 0068; 0070-0072

63
[ 924-88-9 ]
[ 403-54-3 ]
3,6-bis(3-fluorophenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With iron(III) chloride; sodium tert-pentoxide; at 50 - 120℃;	General procedure: A mixture of sodium (2.30 g, 100 mmol), t-amyl alcohol (50 mL) and catalytic amount of FeCl3 were added into a three-necked flask under air. After being stirred vigorously at 100 C for 1 h, the mixture was cooled to 50 C, 3 (40 mmol) was added. Then the mixture was heated to 100 C, <strong>[924-88-9]diisopropyl succinate</strong> (4.00 g, 40 mmol) in t-amyl alcohol (20 mL) was added dropwise over 2 h. Subsequently, the resulting suspension was kept for 3 h at 120 C, and cooled to room temperature. Glacial acetic acid was slowly added till pH was 7.0, followed by methanol and water (1:2, v:v,100 mL) added, the mixture was heated under reflux for 2 h. After cooling filtration and dried, the corresponding product was obtained. The product (2) was used without further purification.
	With iron(III) chloride; sodium; In tert-Amyl alcohol; at 100 - 105℃;	100 ml of tert-amyl alcohol was placed in a 250 ml three-necked flask, and 4 g of sodium was cut into sodium pellets and added to it. Then a catalytic amount of 20-40 mg of ferric chloride was added as a catalyst, heated to 100 ~ 105 C and reacted for 2 ~ 3h. The temperature was lowered to 50-60 C, 68.6 mmol of compound 2-1 was added, and the mixture was further heated to 100-105 C, and 8 ml of a mixture of <strong>[924-88-9]diisopropyl succinate</strong> compound 1 and 40 ml of tert-amyl alcohol was added to three-necked flask using a constant pressure dropping funnel as 3 ~ 5s / d, 2-3h drop. Finally, the mixture was reacted for another 4 hours, the reaction was stopped, the reaction product was poured into a beaker, diluted with 100 ml of methanol, acetic acid was added to adjust the pH to 7, suction-filtered, the filter cake was washed with methanol, the filter cake was heated, dried, heated with N,N-dimethylformamide, cooled, suction-filtered and the filter cake was washed with water and filtered. The filter cake was washed with water and methanol, and the cake was dried by heating to obtain compound 3-1.

Reference： [1]Tetrahedron,2017,vol. 73,p. 494 - 499
[2]Patent: CN109897043,2019,A .Location in patent: Paragraph 0055; 0057-0059

64
[ 924-88-9 ]
[ 64248-63-1 ]
3,6-bis(3,5-difluorophenyl)-2,5-dihydropyrrolo[3,4-c]-pyrrole-1,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With iron(III) chloride; sodium tert-pentoxide; at 50 - 120℃;	General procedure: A mixture of sodium (2.30 g, 100 mmol), t-amyl alcohol (50 mL) and catalytic amount of FeCl3 were added into a three-necked flask under air. After being stirred vigorously at 100 C for 1 h, the mixture was cooled to 50 C, 3 (40 mmol) was added. Then the mixture was heated to 100 C, <strong>[924-88-9]diisopropyl succinate</strong> (4.00 g, 40 mmol) in t-amyl alcohol (20 mL) was added dropwise over 2 h. Subsequently, the resulting suspension was kept for 3 h at 120 C, and cooled to room temperature. Glacial acetic acid was slowly added till pH was 7.0, followed by methanol and water (1:2, v:v,100 mL) added, the mixture was heated under reflux for 2 h. After cooling filtration and dried, the corresponding product was obtained. The product (2) was used without further purification.
	With iron(III) chloride; sodium; In tert-Amyl alcohol; at 100 - 105℃;	100 ml of tert-amyl alcohol was placed in a 250 ml three-necked flask, and 4 g of sodium was cut into sodium pellets, and then acatalytic amount of 20-40 mg of ferric chloride was added as a catalyst. The mixture was heated to 100 ~ 105 C, and reacted for 2 ~ 3h. The temperature was lowered to 50 to 60 C, 68.6 mmol of compound 2-3 was added, and the mixture was further heated to 100 to105 C. 8 ml of a mixture of <strong>[924-88-9]diisopropyl succinate</strong> compound 1 and 40 ml of tert-amyl alcohol were added to a three-necked flask through a constant pressure dropping funnel, 3-5 s/d for 2-3 hours. Finally, the mixture was reacted for another 4 hours, the reaction was stopped, the reaction product was poured into a beaker, diluted with 100 ml of methanol, acetic acid was added to adjust the pH to 7, suction filtered, the filter cake was washed with methanol, the filter cake was dried, heated, hot-melt with N,N-dimethylformamide, cooled and suction filtered, and the filter cake was washed with water and methanol, and the filter cake was taken and dried by heating to obtain the product 3-3.

Reference： [1]Tetrahedron,2017,vol. 73,p. 494 - 499
[2]Patent: CN109897043,2019,A .Location in patent: Paragraph 0081; 0083-0085

65
[ 924-88-9 ]
C₂₇H₄₅NO [ No CAS ]
3,6-bis(4-octyldodecyloxyphenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 4310 - 4319

66
[ 924-88-9 ]
C₂₃H₃₇NO [ No CAS ]
C₅₀H₇₆N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In tert-Amyl alcohol; at 120℃; for 3h;	20 parts by mass of the compound A, 7 parts by mass of <strong>[924-88-9]diisopropyl succinate</strong>, 20 parts by mass of t-amyl alcohol, and 13 parts by mass of potassium t-butoxide were input to a flask and stirred at 120 C. for three hours. After the reaction, 50 parts by mass of methanol and 50 parts by mass of water were added and deposits were filtrated. Blast drying was performed on this crystal at 50 C., so as to obtain 12.2 parts by mass of a compound B.

Reference： [1]Patent: US2017/137444,2017,A1 .Location in patent: Paragraph 0337

67
[ 32431-77-9 ]
[ 924-88-9 ]
C₁₄H₆F₂N₂O₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%		two neck flask equipped with a condenser and an addition funnel was charged with sodium (0.25 g, 10.8 mmol, 1.2 eq.) in 2-methyl-2-butanol (15 mL). The mixture was then heated at 105C until complete consumption of the sodium. 4-Fluoro-2- thiophenecarbonitrile (6) (1.15 g, 9.04 mmol, 1.0 eq.) dissolved in 2-methyl-2-butanol (5 mL) was then rapidly added to the mixture followed by the slow addition of <strong>[924-88-9]diisopropyl succinate</strong> (0.830 mL, 4.7 mmol, 0.45 eq.) through the addition funnel. The reaction mixture quickly turned purple and was stirred overnight at 105C. The reaction mixture was then cooled to 65C, quenched by the addition of a mixture of methanol (30 mL) and acetic acid (10 mL), and followed by heating at 90C over a period of 30 min. The reaction mixture was subsequently allowed to cool to room temperature, filtered using a Buchner funnel and washed with methanol to afford the title compound (Y = 75%). 1H NMR 400 MHz (DMSO) delta (ppm): 11.33 (s, 2H), 8.00 (d, J = 1.8 Hz, 2H), 7.65 (d, J = 1.5 Hz, 2H). 19F NMR 376 MHz (DMSO) delta (ppm): -127.1. 13C NMR 101 MHz (DMSO) delta (ppm): 161.4, 157 (d, J = 256.5 Hz), 136.2, 129.2 (d, J = 9.8 Hz), 119.3 (d, J = 27.5 Hz), 111.4 (d, J = 21.2 Hz), 109.4.

Reference： [1]Macromolecules,2017,vol. 50,p. 7080 - 7090
[2]Patent: WO2019/41047,2019,A1 .Location in patent: Paragraph 00160; 00109

68
[ 924-88-9 ]
[ 116538-95-5 ]
3,6-bis(thieno[3,2-b]pyridin-6-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1 g	With sodium tert-pentoxide; In pentan-1-ol; at 110℃; for 4h;Inert atmosphere;	4) Synthesis of 3,6-bis (thieno [3,2-b] pyridin-6-yl) pyrrolo [3,4- c] pyrrole-1,4 (2H, 5H)Into under the protection of nitrogen,Sodium pentylate (1.72 g, 15.6 mmol) was dissolved in 10 mLspecialPentanolSolution,Thieno [3,2-b] pyridine-6-carbonitrile (1 g, 6.24 mmol) and <strong>[924-88-9]diisopropyl succinate</strong> (0.89 g, 3.02 mmol) were dissolved in20 mL of tert-amyl alcohol,Dropping within one hour, the reaction was completed at 110 for 3 hours after the addition was completed. After the reaction was completed, the reactants were added Poured into a mixed solvent of water and methanol, filtered off with suction and washed with methanol to obtain 1 g of a purple solid. The product can be purified without purification Take the next step.

Reference： [1]Patent: CN106632410,2017,A .Location in patent: Paragraph 0079; 0092

69
[ 924-88-9 ]
[ 65185-41-3 ]
C₂₄H₁₂Br₂N₄O₂ [ No CAS ]

Reference： [1]Advanced Materials,2018,vol. 30

70
[ 924-88-9 ]
2-methylbenzene-1,3,5-tricarbonitrile [ No CAS ]
C₂₄H₁₂N₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A four-necked flask was charged with 126 parts of anhydrous tert-amyl alcohol. After the addition of 12 parts of sodium, the mixture was stirred under reflux until the sodium had reacted completely. At 100 C, 20.6 parts of 3,5-dicyano-4-methylbenzonitrile having the structural formula were added. 16 parts of <strong>[924-88-9]diisopropyl succinate</strong> were added dropwise at 100 C over 1 hour. The mixture was then stirred under reflux for 4 hours. After the reaction suspension has been cooled to 80 degrees celsius, it is poured into a mixture of 150 parts of water and 200 parts of methanol at 25 degrees celsius.The hydrolyzed suspension was stirred under reflux for 6.5 hours, and neutralized by neutral addition to acetic acid. After it was cooled to room temperature, the suspension was filtered, and the pigment was washed with methanol and water. The wet cake was dried in an 80 degree vacuum oven to a moisture content of less than 0.1%, and then ground to obtain 25.6 parts having a structural formula (1- 1) Diketopyrrolopyrrole pigment.

Reference： [1]Patent: CN108239421,2018,A .Location in patent: Paragraph 0031; 0032; 0033

71
[ 613-46-7 ]
[ 924-88-9 ]
[ 84632-55-3 ]

Reference： [1]New Journal of Chemistry,2018,vol. 42,p. 12374 - 12385

72
[ 18791-99-6 ]
[ 924-88-9 ]
3,6-(4-bromo-thiophen-2-yl)pyrrolo[3,4-c]-pyrrole-1,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With tert-Amyl alcohol; sodium; at 105℃;	In a two-neck flask equipped with a condenser and an addition funnel, sodium (3.67 g, 0.159 mol,1.2 eq.) was added in 2-methyl-2-butanol (250 mL, and the mixture was heated at 105 C until completeconsumption of the sodium. Then, <strong>[18791-99-6]4-bromo-2-thiophenecarbonitrile</strong> (1, 25 g, 0.133 mol, 1 eq.) was rapidly added into the mixture, and diisopropyl succinate (12.1 g, 59.8 mmol, 0.45 eq.) was slowly added through the addition funnel. The reaction mixture quickly turned purple. The reaction mixture was stirred overnight at 105 C. The reaction was cooled at 65 C and quenched by an addition of a mixture of methanol (150 mL) and acetic acid (70 mL) followed by heating at 90 C for 30 min. Then,the reaction mixture was allowed to cool to room temperature, filtered on a Buchner, and washed with methanol to give a purple solid (Y = 61%).

Reference： [1]Molecules,2018,vol. 23

73
[ 924-88-9 ]
[ 29147-88-4 ]
C₃₂H₄₀N₂O₄ [ No CAS ]

Reference： [1]Journal of Materials Chemistry B,2018,vol. 6,p. 5570 - 5581

74
[ 623-03-0 ]
[ 924-88-9 ]
Pigment Red 254 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Under a nitrogen atmosphere,40 parts of tert-amyl alcohol dehydrated by molecular sieve and 28 parts of sodium tert-amyl alkoxide were mixed and heated to 100 C. with stirring to prepare an alcoholate solution.On the other hand, a mixture of 24 parts of tert-amyl alcohol dehydrated with molecular sieve, 17.6 parts of <strong>[924-88-9]diisopropyl succinate</strong> and 20 parts of 4-chlorobenzonitrile was heated and dissolved at 90 C. while stirring, It was adjusted. The heated solution of this mixture was slowly added dropwise at a constant rate over 2 hours with vigorous stirring into the previously prepared alcoholate solution. After completion of the dropwise addition, the mixture was heated and stirred at 90 C. for 2 hours to obtain a reaction solution of dichlorodiketopyrrolopyrrole.Next, 120 parts of methanol, 120 parts of water and 23.4 parts of acetic acid were mixed and cooled to 0 C. While stirring this cooled mixture with vigorous stirring, the reaction solution of dichlorodiketopyrrolol obtained at 90 C. previously obtained was added thereto while cooling with a refrigerant so as to keep the temperature at 5 C. or less. After stirring this solution at 40 C. for 1 hour, the dichlorodiketopyrrolate pigment was filtered off using a Nutsche. Thereafter, 120 parts of methanol and 200 parts of water were sprinkled and washed. The filtered pigment was dried at 80 C. for 24 hours to obtain 22.3 parts of the intended pigment.

Reference： [1]Patent: JP2018/158993,2018,A .Location in patent: Paragraph 0126; 0127

75
[ 924-88-9 ]
C₂₅H₄₁NO [ No CAS ]
C₅₄H₈₄N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In tert-Amyl alcohol; at 120℃; for 3h;	21.6 parts by mass of isooctadecanol (FINEOXOCOL 180, manufactured by Nissan Chemical Industries Ltd.) and triethylamine were stirred in 80 parts by mass of toluene, and 10 parts by mass of methanesulfonyl chloride was added dropwise at -10 C. Afier completion of the dropwise addition, a reaction was caused to occur at 30 C. for 2 hours. The organic phase was extracted by liquid separation operation, and the solvent was removed by distillation under reduced pressure. Afier the removal of the solvent, 10.5 parts by mass of 3-cyanophenol, 13.9 parts by mass of potassium carbonate, and 16 parts by mass of dimethylacetamide were added, and the components were caused to react with each other at 100 C. for 24 hours. The organic phase was extracted by liquid separation operation, the organic phase was washed with a sodium hydroxide aqueous solution, and the solvent was removed by distillation under reduced pressure. As a result, 28 parts by mass of a compound A as a light yellow liquid was obtained. 30 parts by mass of the compound A, 9 parts by mass of <strong>[924-88-9]diisopropyl succinate</strong>, 40 parts by mass of tert-amyl alcohol, and 16.5 parts by mass of potassium tert-butoxide were put into a flask and were stirred at 120 C. for 3 hours. Afier the reaction, 100 parts by mass of methanol and 100 parts by mass of water were added, and precipitates were separated by filtration. The crystals were dried by blowing air at 50 C. As a result, 20 parts by mass of a compound B was obtained. 20 parts by mass of the compound B and 9.4 parts by mass of the intermediate a-i were stirred in 400 parts by mass of toluene. Next, 20.9 parts by mass of phosphorus oxychloride was added, and the components were heated to reflux for 4.5 hours. Afier the reaction, the reaction solution was cooled to room temperature, 800 parts by mass of methanol was added, and the components were stirred at room temperature for 30 minutes. The precipitated crystals were separated by filtration and were washed with 400 parts by mass of methanol. The obtained crystals were dried by blowing air at 40 C. for 12 hours. As a result, 13 parts by mass of a compound C was obtained.

Reference： [1]Patent: US2018/305552,2018,A1 .Location in patent: Paragraph 0692

76
[ 924-88-9 ]
C₂₅H₄₁NO [ No CAS ]
C₅₄H₈₄N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In tert-Amyl alcohol; at 120℃; for 6h;	Next, 13 parts by mass of the compound G, 4.2 parts by mass of <strong>[924-88-9]diisopropyl succinate</strong>, 18 parts by mass of t-amyl alcohol, and 7.7 parts by mass of potassium t-butoxide were put into a flask and were stirred at 120 C. for 6 hours. Afier the reaction, 36 parts by mass of methanol and 36 parts by mass of water were added, and precipitates were separated by filtration to obtain crystals. The crystals were dried by blowing air at 50 C. As a result, 5.1 parts by mass of a compound H was obtained.

Reference： [1]Patent: US2018/305552,2018,A1 .Location in patent: Paragraph 0708

77
[ 924-88-9 ]
2-(2-hexyldecyl)thieno[3,4-b]thiophene-6-carbonitrile [ No CAS ]
3,6-bis(2-(2-hexyldecyl)thieno[3,4-b]thiophen-6-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2019,vol. 14,p. 1717 - 1722

78
[ 924-88-9 ]
4-fluoro-5-(dimethyloctylsilyl)-2-thiophenecarbonitrile [ No CAS ]
C₁₄H₆F₂N₂O₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%		A two neck flask equipped with a condenser and an addition funnel was charged with sodium (0.299 g, 13.0 mmol, 1.2 eq.) in 2-methyl-2-butanol (20 mL). The mixture was then heated at 105C until complete consumption of the sodium. 4-Fluoro-5- (dimethyloctylsilyl)-2-thiophenecarbonitrile (8) (3.0 g, 10.1 mmol, 2.1 eq.) dissolved in 2- methyl-2-butanol (5 mL) was then rapidly added to the mixture followed by the slow addition of <strong>[924-88-9]diisopropyl succinate</strong> (0.970 mL, 4.79 mmol, 1.0 eq.) through the addition funnel. The reaction mixture quickly turned purple and was stirred overnight at 105C. The reaction mixture was then cooled to 65C, quenched by the addition of a mixture of methanol (30 mL) and acetic acid (10 mL), and followed by heating at 90C over a period of 2 h. The reaction mixture was subsequently allowed to cool to room temperature, filtered using a Buchner funnel and washed with methanol to afford the title compound (Y = 80%). NMR 400 MHz (DMSO) delta (ppm): 11.33 (s, 2H), 8.00 (d, J = 1.8 Hz, 2H), 7.65 (d, J = 1.5 Hz, 2H). 19F NMR 376 MHz (DMSO) delta (ppm): -127.1. 13C NMR 101 MHz (DMSO) delta (ppm): 161.4, 157 (d, J = 256.5 Hz), 136.2, 129.2 (d, J = 9.8 Hz), 119.3 (d, J = 27.5 Hz), 111.4 (d, J = 21.2 Hz), 109.4.

Reference： [1]Patent: WO2019/41047,2019,A1 .Location in patent: Paragraph 00162; 00112

79
[ 924-88-9 ]
[ 368-77-4 ]
[ 84632-56-4 ]

Yield	Reaction Conditions	Operation in experiment
	With iron(III) chloride; sodium; In tert-Amyl alcohol; at 100 - 105℃;	100 ml of tert-amyl alcohol was added to a 250 ml three-necked flask, and 4 g of sodium was cut into sodium pellets and added to it. Then a catalytic amount of 20-40 mg of ferric chloride was added as a catalyst. The mixture was heated to 100 ~ 105 C, reacted for 2 ~ 3 h. The temperature was lowered to 50 to 60 C, 68.6 mmol of compound 2-4 was added, and the mixture was heated to 100 to 105 C. 8 ml of a mixture of <strong>[924-88-9]diisopropyl succinate</strong> compound 1 and 40 ml of tert-amyl alcohol was added to a three-necked flask through a constant pressure dropping funnel 3-5 s/d for 2-3 hours. Finally, the mixture was reacted for another 4 hours, the reaction was stopped, the reaction product was poured into a beaker, diluted with 100 ml of methanol, acetic acid was added to adjust the pH to 7, suction filtered, the filter cake was washed with methanol, filter cake was taken, heated and dried, hot-melt with N,N-dimethylformamide, cooled and suction filtered, and the filter cake was washed with water and methanol sequentially, and the filter cake was taken, heated and dried by heating to obtain the product 3-4.

Reference： [1]Patent: CN109897043,2019,A .Location in patent: Paragraph 0094; 0096-0098

80
[ 924-88-9 ]
1-cyano-3-trifluoromethoxybenzene [ No CAS ]
C₂₀H₁₀F₆N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With iron(III) chloride; sodium; In tert-Amyl alcohol; at 100 - 105℃;	100 ml of tert-amyl alcohol was placed in a 250 ml three-necked flask, and 4 g of sodium was cut into sodium pellets, and then acatalytic amount of 20-40 mg of ferric chloride was added as a catalyst. Heat to 100 ~ 105 C, the reaction 2 ~ 3h. Thetemperature was lowered to 50 to 60 C, and 68.6 mmol of the compound 2-6 was added, followed by heating to 100 to 105 C.8 ml of a mixture of <strong>[924-88-9]diisopropyl succinate</strong> compound 1 and 40 ml of tert-amyl alcohol was added to a three-necked flask througha constant pressure dropping funnel, and the mixture was 3-5 hours after 2-3 hours. Finally, react for another 4 hours, stop thereaction, pour the reaction product into a beaker, dilute with 100 ml of methanol, add acetic acid to adjust the pH to 7, filter withsuction, wash the filter cake with methanol, take the filter cake, heat and dry, then use N, The N-dimethylformamide is thermallydissolved, cooled and suction filtered, and the filter cake is washed with water and methanol, and the filter cake is taken anddried by heating to obtain the product 3-6.

Reference： [1]Patent: CN109897043,2019,A .Location in patent: Paragraph 0120; 0122-0124

81
[ 924-88-9 ]
[ 332-25-2 ]
C₂₀H₁₀F₆N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With iron(III) chloride; sodium; In tert-Amyl alcohol; at 100 - 105℃;	100 ml of tert-amyl alcohol was placed in a 250 ml three-necked flask, and 4 g of sodium was cut into sodium pellets, and then acatalytic amount of 20-40 mg of ferric chloride was added as a catalyst. Heat to 100 ~ 105 ° C, the reaction 2 ~ 3h. Thetemperature was lowered to 50 to 60 ° C, and 68.6 mmol of the compound 2-7 was added, followed by heating to 100 to 105 °C.8 ml of a mixture of diisopropyl succinate compound 1 and 40 ml of tert-amyl alcohol was added to a three-necked flask througha constant pressure dropping funnel, and the mixture was 3-5 hours after 2-3 hours. Finally, react for another 4 hours, stop thereaction, pour the reaction product into a beaker, dilute with 100 ml of methanol, add acetic acid to adjust the pH to 7, filter withsuction, wash the filter cake with methanol, take the filter cake, heat and dry, then use N, The N-dimethylformamide is thermallydissolved, cooled and suction filtered, and the filter cake is washed with water and methanol, and the filter cake is taken anddried by heating to obtain the product 3-7.

Reference： [1]Patent: CN109897043,2019,A .Location in patent: Paragraph 0133; 0135-0137

82
[ 924-88-9 ]
[ 620-22-4 ]
[ 84632-53-1 ]

Yield	Reaction Conditions	Operation in experiment
63%	With iron(III) chloride; sodium; In tert-Amyl alcohol; at 100℃; for 3h;Inert atmosphere;	Take a 250 mL three-necked flask, add 100 mL of dry tert-amyl alcohol, sodium particles (4.0 g, 100 mmol), 10 mg of ferric chloride, raise the temperature to 100 C, and heat and stir under nitrogen for about 30 min.The sodium particles are completely dissolved.Then cool down to about 50 C,Then add to the system3-methylbenzonitrile compound 1-2 (8.0 g, 68.6 mmol),The temperature was then raised to 100 C.Dilute with 30 mL of tert-amyl alcoholDiisopropyl diacrylate compound 2 (8 mL, 39.6 mmol),The mixture was slowly dropped into a three-necked flask using a constant pressure dropping funnel.It takes 2-3 hours.After the completion of the dropwise addition, the reaction solution was continued to react for 3 hours.After the reaction was completed, the reaction mixture was poured into a clean 500 mL beaker and naturally cooled to room temperature.Slowly add glacial acetic acid to the beaker until the pH is neutral, at which point a large amount of solids precipitate.Filter through a Buchner funnel and wash the filter cake with methanol and water until the filtrate is colorless and transparent.Dry the filter cake to obtain a bright red solid powderAt the end of the compound 3-2, the yield was 63%.

Reference： [1]Patent: CN109897045,2019,A .Location in patent: Paragraph 0062-0064

83
[ 924-88-9 ]
[ 6575-00-4 ]
[ 88949-36-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With iron(III) chloride; sodium; In tert-Amyl alcohol; at 100℃; for 3h;Inert atmosphere;	Take a 250 mL three-necked flask, add 100 mL of dry tert-amyl alcohol, sodium particles (4.0 g, 100 mmol), 10 mg of ferric chloride, raise the temperature to 100 C, heat and stir under nitrogen for about 30 min, dissolve the sodium particles completely, then cool down to Around 50 C,Then, <strong>[6575-00-4]3,5-<strong>[6575-00-4]dichlorobenzonitrile</strong></strong>, compound 1-3 (7.5 g, 68.6 mmol) was added to the system, and the temperature was raised to 100 C, and diisopropyl succinate compound 2 was diluted with 30 mL of tert-amyl alcohol ( 8 mL, 39.6 mmol), and the mixture was slowly dropped into a three-necked flask using a constant pressure dropping funnel for 2-3 hours. After the addition was completed, the reaction solution was further reacted for 3 hours.After the reaction was completed, the reaction mixture was poured into a clean 500 mL beaker and naturally cooled to room temperature. Slowly add glacial acetic acid to the beaker until the pH is neutral, at which point a large amount of solids precipitate. The Buchner funnel was suction filtered and the filter cake was washed with methanol and water until the filtrate was colorless and transparent. The filter cake was dried to give a red-purple solid powder, Compound 3-3, in a yield of 85%.

Reference： [1]Patent: CN109897045,2019,A .Location in patent: Paragraph 0067-0069

84
[ 108-30-5 ]
[ 67-63-0 ]
[ 924-88-9 ]

Yield	Reaction Conditions	Operation in experiment
	With A45 acid resin; SO42-/SnO2-ZrO2 nano solid super acid; at 80 - 90℃;	(1) The A45 acid resin catalyst is treated with isopropanol to remove the water content of the catalyst. Then, the A45 acid resin catalyst is packed in the reaction tower (1) and the reaction tower (2), the loading factor is controlled to 70%, and expansion space is reserved.(2) The nano-solid superacid prepared in Example 4 is packed in the reaction tower (3), and the loading factor is controlled to 30%.(3) The reaction materials succinic anhydride and isopropanol are preheated at a molar ratio of 1: 2.5 and mixed, and the space velocity is 1h-1 through three reaction columns connected in series.(4) The cooling water adopts a countercurrent method to heat exchange three reaction towers at the same time, taking away excess reaction heat and controlling the reaction temperature at 80-90 C.(5) The product was purified by distillation with a distillation column, and the product at 228 C was collected.Analytical product yield before analysis was 99.2%, purity was 98.7% (not counting unreacted isopropanol), and purity after distillation was 99.6%.

Reference： [1]Patent: CN110256244,2019,A .Location in patent: Paragraph 0032-0088

85
[ 75-85-4 ]
[ 221295-04-1 ]
[ 924-88-9 ]
C₂₄H₂₈N₆O₄ [ No CAS ]
C₂₂H₂₄N₆O₄ [ No CAS ]
C₂₀H₂₀N₆O₄ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 20215 - 20221

86
[ 75-85-4 ]
[ 221295-04-1 ]
[ 924-88-9 ]
[ 1413918-72-5 ]
C₈₈H₁₅₆N₆O₄ [ No CAS ]
C₈₆H₁₅₂N₆O₄ [ No CAS ]
C₈₄H₁₄₈N₆O₄ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 20215 - 20221

87
[ 75-85-4 ]
[ 221295-04-1 ]
[ 924-88-9 ]
[ 1413918-72-5 ]
C₇₈H₁₃₆N₆O₄ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 20215 - 20221

88
[ 7283-70-7 ]
[ 924-88-9 ]

Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 2760 - 2763
Angew. Chem.,2020,vol. 132,p. 2760 - 2785,26

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	924-88-9	MDL No. :	MFCD00059360
Formula :	C₁₀H₁₈O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YPLYFEUBZLLLIY-UHFFFAOYSA-N
M.W :	202.25	Pubchem ID :	70213
Synonyms :

Num. heavy atoms :	14
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.8
Num. rotatable bonds :	7
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	52.75
TPSA :	52.6 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.49 cm/s

Log Po/w (iLOGP) :	2.41
Log Po/w (XLOGP3) :	1.47
Log Po/w (WLOGP) :	1.67
Log Po/w (MLOGP) :	1.55
Log Po/w (SILICOS-IT) :	1.66
Consensus Log Po/w :	1.75

[ CAS No. 924-88-9 ] {[proInfo.proName]}

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Safety of [ 924-88-9 ]

Application In Synthesis of [ 924-88-9 ]

[ 924-88-9 ] Synthesis Path-Upstream 1~6

[ 924-88-9 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 924-88-9 ]

Esters

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Log S (ESOL) :	-1.56
Solubility :	5.6 mg/ml ; 0.0277 mol/l
Class :	Very soluble
Log S (Ali) :	-2.18
Solubility :	1.33 mg/ml ; 0.00659 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.72
Solubility :	3.85 mg/ml ; 0.0191 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.16

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 924-88-9 ] {[proInfo.proName]}

Quality Control of [ 924-88-9 ]

Related Doc. of [ 924-88-9 ]

Product Details of [ 924-88-9 ]

Calculated chemistry of [ 924-88-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 924-88-9 ]

Application In Synthesis of [ 924-88-9 ]

[ 924-88-9 ] Synthesis Path-Upstream 1~6

[ 924-88-9 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 924-88-9 ]

Esters

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 924-88-9 ]