[ CAS No. 91-15-6 ] {[proInfo.proName]}

Name: 91-15-6|Phthalonitrile|95%
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Quality Control of [ 91-15-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 91-15-6 ]

CAS No. :	91-15-6	MDL No. :	MFCD00001771
Formula :	C₈H₄N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XQZYPMVTSDWCCE-UHFFFAOYSA-N
M.W :	128.13	Pubchem ID :	7042
Synonyms :

Safety of [ 91-15-6 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P273-P260-P270-P264-P308+P311-P301+P310+P330-P405-P501	UN#:	3439
Hazard Statements:	H301-H370-H372-H373-H412	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 91-15-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 91-15-6 ]
Downstream synthetic route of [ 91-15-6 ]

[ 91-15-6 ] Synthesis Path-Upstream 1~16

1
[ 51-17-2 ]
[ 67-66-3 ]
[ 1448-87-9 ]
[ 91-15-6 ]

Reference： [1] Journal of Chemical Research, Miniprint, 1980, # 12, p. 4935 - 4953

2
[ 91-15-6 ]
[ 89898-86-2 ]

Reference： [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 8, p. 1329 - 1340

3
[ 253-52-1 ]
[ 87-41-2 ]
[ 7468-67-9 ]
[ 89898-86-2 ]
[ 91-15-6 ]

Reference： [1] Chemosphere, 1999, vol. 38, # 2, p. 351 - 361

4
[ 615-42-9 ]
[ 4387-36-4 ]
[ 91-15-6 ]

Reference： [1] Canadian Journal of Chemistry, 1985, vol. 63, p. 111 - 120

5
[ 91-15-6 ]
[ 88-96-0 ]

Reference： [1] ChemSusChem, 2012, vol. 5, # 8, p. 1392 - 1396
[2] ChemSusChem, 2011, vol. 4, # 1, p. 104 - 111
[3] ChemCatChem, 2018, vol. 10, # 2, p. 449 - 458

6
[ 91-15-6 ]
[ 88-96-0 ]
[ 17174-98-0 ]

Reference： [1] ChemCatChem, 2018, vol. 10, # 2, p. 449 - 458

7
[ 91-15-6 ]
[ 31643-49-9 ]
[ 51762-67-5 ]

Reference： [1] Organic and Biomolecular Chemistry, 2003, vol. 1, # 13, p. 2326 - 2335

8
[ 35963-33-8 ]
[ 91-15-6 ]
[ 83-41-0 ]

Reference： [1] Journal of the American Chemical Society, 1986, vol. 108, # 18, p. 5453 - 5459

9
[ 38442-51-2 ]
[ 91-15-6 ]
[ 32703-80-3 ]
[ 36360-48-2 ]

Reference： [1] Journal of the American Chemical Society, 1997, vol. 119, # 38, p. 8795 - 8801
[2] Journal of the American Chemical Society, 1997, vol. 119, # 38, p. 8795 - 8801

10
[ 558-17-8 ]
[ 91-15-6 ]
[ 32703-80-3 ]

Reference： [1] Journal of Organic Chemistry, 1998, vol. 63, # 26, p. 9956 - 9959

11
[ 507-19-7 ]
[ 91-15-6 ]
[ 32703-80-3 ]

Reference： [1] Journal of Organic Chemistry, 1998, vol. 63, # 26, p. 9956 - 9959

12
[ 109-65-9 ]
[ 507-19-7 ]
[ 91-15-6 ]
[ 68527-72-0 ]
[ 32703-80-3 ]
[ 57775-05-0 ]

Reference： [1] Russian Journal of Organic Chemistry, 1998, vol. 34, # 11, p. 1632 - 1639

13
[ 542-69-8 ]
[ 558-17-8 ]
[ 91-15-6 ]
[ 68527-72-0 ]
[ 32703-80-3 ]
[ 57775-05-0 ]

Reference： [1] Russian Journal of Organic Chemistry, 1998, vol. 34, # 11, p. 1632 - 1639

14
[ 91-15-6 ]
[ 32372-82-0 ]

Yield	Reaction Conditions	Operation in experiment
33%	Stage #1: With C₄₆H₁₇₈O₄₁Si₄₂; titanium(IV)isopropoxide In toluene at 100℃; for 24 h; Inert atmosphere Stage #2: With hydrogenchloride; water In toluene at 20℃; for 4 h; Inert atmosphere	General procedure: To a 50 mL round-bottom flask, under nitrogen atmosphere, containing dinitriles 1p (500 mg, 4.2 mmol, 1.0 equiv) in 5.0 mL of toluene were added PMHS (1.0 mL, 16.8 mmol, 4.0 equiv) and Ti(Oi-Pr)₄ (1.3 mL, 4.3 mmol, 1.0 equiv). The mixture was then heated at 100°C for 24 h (the colorless solution turned into deep purple). After cooling to rt, the clear solution was diluted in toluene (30 mL) and hydrolyzed with aqueous 1M HCl (15 mL, 3.6 equiv) for 4 h (until the deep purple solution became yellow). The crude mixture was then concentrated under reduced pressure. The resulting solid was filtered, washed with pentane (60 mL), dissolved in chloroform and filtrate on a pad of Celite^®. The filtrate was finally concentrated under reduced pressure affording the amine 3p as a hydrochloride salt.

Reference： [1] Tetrahedron, 2014, vol. 70, # 4, p. 975 - 983

15
[ 91-15-6 ]
[ 70484-01-4 ]
[ 86938-64-9 ]

Reference： [1] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 1998, vol. 54, # 2, p. 305 - 317

16
[ 91-15-6 ]
[ 102072-84-4 ]

Reference： [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 8, p. 1329 - 1340

[ 91-15-6 ] Synthesis Path-Downstream 1~88

1
[ 88-96-0 ]
[ 91-15-6 ]

Reference： [1]Patent: US2232836,1939,
[2]Patent: CH205159,1937,
[3]Patent: CH205159,1937,
[4]Patent: CH205159,1937,
[5]Patent: US2387435,1939,
[6]Patent: US2387435,1939,
[7]Journal of the Chemical Society,1934,p. 1022
[8],1955,vol. 50,p. 19
    Chem.Abstr.,1956,p. 9035
[9]Patent: DE729961,1940,
    DRP/DRBP Org.Chem.,
[10]Bulletin de la Societe Chimique de France,1958,p. 409,413
[11]Journal of the American Chemical Society,1930,vol. 52,p. 4082,4086
[12]Patent: DE706198,1937,
    DRP/DRBP Org.Chem.,
[13]Patent: DE706198,1937,
    DRP/DRBP Org.Chem.,
[14]Patent: DE706198,1937,
    DRP/DRBP Org.Chem.,
[15]Patent: DE706198,1937,
    DRP/DRBP Org.Chem.,
[16]Patent: DE651611,1935,
[17]Patent: DE651611,1935,
[18]Patent: US2054088,1934,

2
[ 88-96-0 ]
[ 17174-98-0 ]
[ 91-15-6 ]

Reference： [1]Chemische Berichte,1907,vol. 40,p. 2709

3
[ 88-96-0 ]
[ 108-24-7 ]
[ 136918-14-4 ]
[ 1971-49-9 ]
[ 17174-98-0 ]
[ 91-15-6 ]

Reference： [1]Chemische Berichte,1907,vol. 40,p. 2713

4
[ 91-15-6 ]
[ 496-12-8 ]

Yield	Reaction Conditions	Operation in experiment
75%	platinum; In tetrahydrofuran;	EXAMPLE 1 Isoindoline The reaction was carried out in an autoclave. 20 g of 5% platinum on carbon are added to 100 g of phthalonitrile dissolved in tetrahydrofuran. After purging with nitrogen, the mixture is heated at 60 C. and a hydrogen pressure of 180 bars is applied for 5 to 6 hours. After decompression and purging with nitrogen, the catalyst is removed by filtration. The tetrahydrofuran is distilled off from the filtrate at atmospheric pressure, and then isoindoline is in turn distilled off from the residue under a vacuum of 23 mbars. at a temperature of 100 C. Isoindoline is thus obtained with a yield of 75% and purity of 89%.

Reference： [1]Patent: US2001/23294,2001,A1
[2]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1959,p. 1858; engl. Ausg. S. 1778
[3]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1959,p. 1858; engl. Ausg. S. 1778

5
[ 41995-30-6 ]
[ 91-15-6 ]
[ 81560-15-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,1981,vol. 18,p. 1613 - 1618

6
[ 823-39-2 ]
[ 91-15-6 ]
[ 81560-14-7 ]

Reference： [1]Journal of Heterocyclic Chemistry,1981,vol. 18,p. 1613 - 1618

7
[ 124-68-5 ]
[ 91-15-6 ]
[ 131380-84-2 ]

Yield	Reaction Conditions	Operation in experiment
82%		Example 2 Synthesis of 2,2-(1,2-Phenylene)bis(4,4-Dimethyl-4,5-Dihydrooxazole) A solution of phthalonitrile (4.0 mmol) and zinc triflate (5.0 mol %, 0.2 mmol) in dried chlorobenzene (30 ml) was stirred at room temperature for 15 min. A solution of <strong>[124-68-5]2-amino-2-methyl-1-propanol</strong> (8.0 mmol) in dry chlorobenzene (5 ml) was slowly added. The temperature was raised to 135 C. and the reaction mixture was refluxed for 24 h. The product of the reaction, obtained as an oily residue, was dissolved in 30 ml of dichloromethane and extracted twice with distilled water (2*20 ml). The aqueous layer was then separated and the combined organic layers were dried with anhydrous sodium sulfate. The dichloromethane was removed using a rotary evaporator to obtain the impure product, which was then purified using silica gel column chromatography with dichloromethane-ether (4:1) as eluent (Ibrahim, M. B.; El Ali, B.; Fettouhi, M.; Ouahab, L. Appl. Organometal. Chem. 2015, 29, 400, incorporated herein by reference in its entirety).

Reference： [1]Synthetic Communications,1996,vol. 26,p. 1335 - 1340
[2]Tetrahedron Letters,1998,vol. 39,p. 459 - 462
[3]Applied Organometallic Chemistry,2015,vol. 29,p. 400 - 407
[4]Patent: US9546191,2017,B1 .Location in patent: Page/Page column 13
[5]Chemische Berichte,1991,vol. 124,p. 1173 - 1180

8
[ 24629-25-2 ]
[ 91-15-6 ]
[ 131380-81-9 ]

Reference： [1]Chemische Berichte,1991,vol. 124,p. 1173 - 1180

9
[ 38442-51-2 ]
[ 91-15-6 ]
[ 32703-80-3 ]
[ 36360-48-2 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 8795 - 8801
[2]Journal of the American Chemical Society,1997,vol. 119,p. 8795 - 8801

10
[ 91-15-6 ]
[ 70484-01-4 ]
[ 86938-64-9 ]
3,6-dibromophthalodinitrile [ No CAS ]

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,1998,vol. 54,p. 305 - 317

11
[ 253-52-1 ]
[ 87-41-2 ]
[ 7468-67-9 ]
[ 89898-86-2 ]
[ 91-15-6 ]

Reference： [1]Chemosphere,1999,vol. 38,p. 351 - 361

12
[ 2937-81-7 ]
[ 91-15-6 ]
C₂₀H₁₀N₁₀S₂ [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,1997,vol. 31,p. 409 - 412

13
[ 558-17-8 ]
[ 91-15-6 ]
[ 32703-80-3 ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 9956 - 9959

14
[ 507-19-7 ]
[ 91-15-6 ]
[ 32703-80-3 ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 9956 - 9959

15
[ 88-97-1 ]
ammonia-stream [ No CAS ]
thorium oxide [ No CAS ]
[ 91-15-6 ]

Reference： [1]Patent: US2232836,1939,

16
[ 109-65-9 ]
[ 507-19-7 ]
[ 91-15-6 ]
[ 68527-72-0 ]
[ 32703-80-3 ]
[ 57775-05-0 ]
2-Butyl-5-(tert-butyl)benzonitrile [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,1998,vol. 34,p. 1632 - 1639

17
[ 542-69-8 ]
[ 558-17-8 ]
[ 91-15-6 ]
[ 68527-72-0 ]
[ 32703-80-3 ]
[ 57775-05-0 ]
2-Butyl-5-(tert-butyl)benzonitrile [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,1998,vol. 34,p. 1632 - 1639

18
[ 2346-00-1 ]
[ 91-15-6 ]
3-[(Z)-1-(4,5-dihydro-1,3-thiazol-2-yl)methylidene]-2,3-dihydro-1H-isoindol-1-imine [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2001,p. 1195 - 1201

19
[ 3333-52-6 ]
[ 91-15-6 ]
[ 13930-88-6 ]
C₃₂H₃₂N₈OV [ No CAS ]
C₃₂H₃₂N₈OV [ No CAS ]
C₃₂H₂₄N₈OV [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2001,vol. 71,p. 821 - 822

20
[ 3333-52-6 ]
[ 91-15-6 ]
[ 574-93-6 ]
7,7,8,8-tetramethyltribenzo[b,l,q]tetraazachlorin [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2001,vol. 71,p. 821 - 822

21
[ 3333-52-6 ]
[ 91-15-6 ]
C₃₂H₂₄N₈^(2-)*Cu⁽²⁺⁾ [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2001,vol. 71,p. 821 - 822

22
[ 3333-52-6 ]
[ 91-15-6 ]
C₃₂H₂₄N₈^(2-)*Ni⁽²⁺⁾ [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2001,vol. 71,p. 821 - 822

23
[ 91-15-6 ]
[ 147-14-8 ]

Reference： [1]Molecules,2001,vol. 6,p. 831 - 844
[2]Tetrahedron,2005,vol. 61,p. 179 - 188
[3]Synthesis,2007,p. 3713 - 3721
[4]Synlett,2002,p. 1649 - 1652

24
[ 3333-52-6 ]
[ 91-15-6 ]
7,7,8,8-tetramethyltribenzo[b,l,q]tetraazachlorin [ No CAS ]

Reference： [1]Chemistry - A European Journal,2004,vol. 10,p. 117 - 133

25
[ 3333-52-6 ]
[ 91-15-6 ]
C₃₂H₂₄N₈^(2-)*Ni⁽²⁺⁾ [ No CAS ]
C₃₂H₃₂N₈^(2-)*Ni⁽²⁺⁾ [ No CAS ]
C₃₂H₃₂N₈^(2-)*Ni⁽²⁺⁾ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2004,vol. 10,p. 117 - 133

26
[ 3333-52-6 ]
[ 91-15-6 ]
C₃₂H₃₂N₈^(2-)*OV⁽²⁺⁾ [ No CAS ]
C₃₂H₃₂N₈^(2-)*OV⁽²⁺⁾ [ No CAS ]
C₃₂H₂₄N₈^(2-)*OV⁽²⁺⁾ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2004,vol. 10,p. 117 - 133

27
[ 69518-17-8 ]
[ 91-15-6 ]
chloro[2-iodo-7,12:14,19-diimino-21,5-nitrilo-5H-tribenzo[c,h,m][1,6,11]triazacyclopentadecinato(2-)-κN²²,κN²³,κN²⁴]-boron(III) [ No CAS ]

Reference： [1]Chemistry - A European Journal,2005,vol. 11,p. 3881 - 3893

28
[ 3619-17-8 ]
[ 91-15-6 ]
N'-(3-amino-1H-isoindol-1-ylidene)-2-methytlpropanohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In methanol for 5h; Heating;

Reference： [1]Hordiyenko, Olha V.; Biitseva, Angelina V.; Kornilov, Mikhail Yu.; Brosse, Nicolas; Hocquet, Alexandre; Jamart-Gregoire, Brigitte; Shishkin, Oleg V.; Zubatyuk, Roman I. [European Journal of Organic Chemistry, 2006, # 12, p. 2833 - 2842]

29
[ 7051-34-5 ]
[ 91-15-6 ]
2-(cyclopropylmethyl)benzonitrile [ No CAS ]
4-(but-3-en-1-yl)phthalonitrile [ No CAS ]
4-(cyclopropylmethyl)phthalonitrile [ No CAS ]
[ 62170-45-0 ]

Reference： [1]Russian Journal of Organic Chemistry,2006,vol. 42,p. 1280 - 1288

30
[ 823-61-0 ]
[ 91-15-6 ]
1,3-bis(3,6-dimethyl-2-pyridylimino)isoindoline [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2007,p. 3208 - 3216

31
[ 91-15-6 ]
[ 102072-84-4 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 1329 - 1340

32
[ 91-15-6 ]
[ 89898-86-2 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 1329 - 1340

33
[ 7446-70-0 ]
[ 91-15-6 ]
[ 14154-42-8 ]

Yield	Reaction Conditions	Operation in experiment
92.5%	With 1-Chloronaphthalene; In water; acetone; toluene; at 70 - 240℃; for 10h;	Synthesis Example 5 Synthesis of chloroaluminum phthalocyanine (A method described in Synthesis Example 1 of Japanese Patent Kokai Publication No. H9(1997) 217020) Phthalonitrile (180.0 g, (1.41 mol)), 900 ml of 1-chloronaphthalene and 47.0 g (0.353 mol) of aluminum (III) chloride were charged into a four-necked flask, and heated and stirred under reflux at 240C for 6 hours. Thereafter, the reflux was stopped and the mixture was allowed to cool to a temperature of approximately 130C, and thereafter was filtered under heating, sprinkled and washed with 1800 ml of hot toluene (100C), 80 ml of toluene and 900 ml of acetone, and substituted with 100 ml of toluene. The obtained cake was stirred and refluxed in 750 ml of toluene for 3 hours, thereafter filtered under heating at 100C, and thereafter was washed with 1800 ml of hot toluene (100C), 180 ml of toluene and 900 ml of acetone, and the solvent was substituted with 400 ml of water. The obtained cake was added to 4500 ml of water and heat-dispersed at 70C for 1 hour. After being filtered under heating, the obtained cake was washed with 900 ml of acetone and 1000 ml of water, and dried at 70C to obtain 187.6 g of chloroaluminum phthalocyanine ClAlPc (yield: 92.5%).
92.5%		Synthesis Example 7 Synthesis of chloroaluminum phthalocyanine ClAlPc (A method described in Synthesis Example 1 of Japanese Patent Laid-Open Publication No. H9(1997) 217020) 180.0 g (1.41 mol) of phthalonitrile, 900 ml of 1-chloronaphthalene and 47.0 g (0.353 mol) of aluminum (III) chloride were charged into a four-necked flask, and heated and stirred under reflux at a temperature of 240C for 6 hours. Thereafter, the reflux was stopped and the mixture stood to cool to a temperature of approximately 130C, and thereafter was filtered under heating, sprinkled and washed with 1800 ml of hot toluene (100C), 80 ml of toluene and 900 ml of acetone, and substituted with 100 ml of toluene. The obtained cake was stirred and refluxed in 750 ml of toluene for 3 hours, thereafter filtered under heating at a temperature of 100C, and thereafter was washed with 1800 ml of hot toluene (100C), 180 ml of toluene and 900 ml of acetone, and the solvent was substituted with 400 ml of water. The obtained cake was added to 4500 ml of water and heat-dispersed at a temperature of 70C for 1 hour. After being filtered under heating, the obtained cake was washed with 900 ml of acetone and 1000 ml of water, and dried at a temperature of 70C to obtain 187.6 g of chloroaluminum phthalocyanine ClAlPc (yields 92.5%).
84.5%	at 200℃; for 15h;	Example 1 Comparative Method-No Ammonium Salt A chloroaluminum phthalocyanine pigment (Pigment 1) was prepared by adding 614.4 g phthalonitrile, 160.0 g anhydrous aluminum(III) chloride and 3248 g dichlorotoluenes (isomer mixture) to a 4 L glass kettle. The reaction mixture was stirred as the temperature was raised to 200 C. over a period of two hours and maintained for an additional 13 hours at 200 C. before cooling to room temperature. After cooling, the solvent was removed by vacuum distillation to obtain a crude phthalocyanine reaction product. The crude phthalocyanine reaction product was purified by preparing a slurry in 2.5 L of 1% aqueous sulfuric acid and heating to 90 C. for two hours with stirring, followed by filtration at 90 C., washing with water until the filtrate was neutralized, and drying at 80 C. to obtain 582.35 g (84.5%) of a purified reaction product.

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In pentan-1-ol; at 136℃; for 5h;

225 parts of phthalodinitrile and 78 parts of aluminum chloride anhydride were added to 1250 parts of n-amyl alcohol in a reaction vessel and stirred. To this, 266 parts of DBU (1,8-Diazabicyclo [5.4.0] undec-7-ene) was added, the temperature was raised and refluxed at 136 C. for 5 hours. The reaction solution cooled to 30 C. with stirring was injected into a mixed solvent of 5000 parts of methanol and 10000 parts of water under stirring to obtain a blue slurry. The slurry was filtered, washed with a mixed solvent of 2000 parts of methanol and 4000 parts of water, and dried to obtain 135 parts of chloroaluminum phthalocyanine

Reference： [1]Patent: EP1514904,2005,A1 .Location in patent: Page/Page column 7
[2]Patent: EP1418207,2004,A1 .Location in patent: Page 9
[3]Patent: US2014/179915,2014,A1 .Location in patent: Paragraph 0131
[4]RSC Advances,2015,vol. 5,p. 45731 - 45739
[5]Patent: JP2015/110690,2015,A .Location in patent: Paragraph 0152

34
[ 7787-87-3 ]
[ 30757-50-7 ]
[ 91-15-6 ]

Yield	Reaction Conditions	Operation in experiment
77.0%	With hydrogenchloride; potassium carbonate; In N,N-dimethyl-formamide;	Preparation Example 4 Preparation of Phthalonitrile : In 200 ml of N,N-dimethylformamide were dissolved with heating 20 g of <strong>[30757-50-7]4-hydroxyphthalonitrile</strong> and 10.55 g of potassium carbonate, to which 20 g of chloroethyl- trimethylsilane were added dropwise at 40C in the atmosphere of argon. Immediately after the addition, the mixture was stirred for 18 hours while maintaining the reaction temperature at 85-105C. The reaction vessel was then cooled to room temperature and 250 ml of dilute hydrochloric acid was added. The mixture was extracted with 1.2 liters of toluene. The organic layer was washed well with water and water was removed with magnesium sulfate. Thereafter, toluene was removed by distillation and the residue was purified with a toluene/silica gel column to obtain 24.6 g (yield: 77.0 %) of a compound having the formula (XVII) below.

Reference： [1]Patent: EP676299,1995,A1

35
[ 4733-50-0 ]
[ 2344-80-1 ]
[ 91-15-6 ]

Yield	Reaction Conditions	Operation in experiment
84.8%	With hydrogenchloride; potassium carbonate; In N,N-dimethyl-formamide;	Preparation Example 7 Preparation of Phthalonitrile : In 200 ml of N,N-dimethylformamide were dissolved with heating 30 g (0.1875 mole) of 2,3-dicyanohydroquinone and 25.91 g (0.1875 mole) of potassium carbonate, to which 50.5 g (0.4125 mole) of chloromethyltrimethylsilane were added dropwise at 40C in the atmosphere of argon. After the addition, the mixture was stirred for 30 hours while maintaining the reaction temperature at 80-90C. The reaction vessel was then cooled to room temperature and 300 ml of dilute hydrochloric acid was added. The mixture was extracted with 1.5 liters of chloroform. The organic layer was washed well with water and water was removed with magnesium sulfate. Thereafter, chloroform was removed by distillation and the residue was purified with a toluene/silica gel column to obtain 52.8 g (yield: 84.8 %) of a compound having the formula (XXI) below. The compound is in the form of white crystals and has a melting point of 143-144C. The IR spectrum and NMR spectrum of the compound are shown in Figs. 6 and 7, respectively.

Reference： [1]Patent: EP676299,1995,A1

36
[ 32703-80-3 ]
[ 91-15-6 ]
[ 14320-04-8 ]
[ 118681-06-4 ]

Reference： [1]Chemistry Letters,1988,p. 1359 - 1362

37
[ 91-22-5 ]
[ 7446-70-0 ]
[ 91-15-6 ]
[ 14154-42-8 ]

Reference： [1]Physica Status Solidi (A) Applied Research,1994,vol. 144,p. 91 - 104
[2]Journal of Physics and Chemistry of Solids,1997,vol. 58,p. 711 - 716

38
[ 7446-70-0 ]
[ 91-15-6 ]
[ 14154-42-8 ]

Reference： [1]Chemistry Letters,1986,p. 1259 - 1262
[2]Journal of Physical Chemistry,1996,vol. 100,p. 7632 - 7645
[3]Journal of the Electrochemical Society,1987,vol. 134,p. 1148 - 1152

39
[ 14024-63-6 ]
[ 91-15-6 ]
[ 14320-04-8 ]

Reference： [1]Chemistry Letters,1983,p. 313 - 316

40
[ 91054-33-0 ]
[ 91-15-6 ]
copper(l) chloride [ No CAS ]
[ 52647-45-7 ]

Reference： [1]Liebigs Annalen der Chemie,1937,vol. 531,p. 279 - 287
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Cu: MVol.B4, 141, page 1757 - 1760

41
[ 91054-33-0 ]
[ 91-15-6 ]
copper(l) chloride [ No CAS ]
{CuC₃₄H₁₈N₆} [ No CAS ]

Reference： [1]Liebigs Annalen der Chemie,1937,vol. 531,p. 279 - 287
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Cu: MVol.B4, 141, page 1757 - 1760

42
[ 91-22-5 ]
[ 13465-09-3 ]
[ 91-15-6 ]
[ 93976-63-7 ]

Reference： [1]Physica Status Solidi (A) Applied Research,1994,vol. 144,p. 91 - 104

43
[ 22306-37-2 ]
[ 91-15-6 ]
tris(phthalocyaninato)dibismuth(III) [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2000,p. 1771 - 1779

44
[ 7727-37-9 ]
[ 22306-37-2 ]
[ 91-15-6 ]
[ 351038-17-0 ]

Reference： [1]European Journal of Inorganic Chemistry,2001,p. 1343 - 1352

45
[ 3333-52-6 ]
[ 91-15-6 ]
copper(l) chloride [ No CAS ]
[ 523987-29-3 ]

Reference： [1]Russian Journal of General Chemistry,2001,vol. 71,p. 821 - 822

46
[ 3333-52-6 ]
[ 7718-98-1 ]
[ 91-15-6 ]
[ 13930-88-6 ]
VO((C₆H₄(CN)2)2((C(CH₃)2CN)2)2) [ No CAS ]
VO((C₆H₄(CN)2)3((C(CH₃)2CN)2)) [ No CAS ]
VO((C₆H₄(CN)2)2((C(CH₃)2CN)2)2) [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2001,vol. 71,p. 821 - 822

47
[ 3333-52-6 ]
[ 91-15-6 ]
nickel dichloride [ No CAS ]
[ 523987-28-2 ]

Reference： [1]Russian Journal of General Chemistry,2001,vol. 71,p. 821 - 822

48
[ 366-18-7 ]
[ 1295-35-8 ]
[ 91-15-6 ]
[ 191534-07-3 ]

Reference： [1]Journal of Organometallic Chemistry,1997,vol. 532,p. 267 - 270

49
[ 10025-74-8 ]
[ 7732-18-5 ]
[ 88-99-3 ]
[ 91-15-6 ]
Dy₂(H₂O)4 bis(benzene-1,2-dicarboxylate)(terphthalate) [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2004,p. 762 - 770

50
[ 13465-09-3 ]
[ 91-15-6 ]
[ 93976-63-7 ]

Reference： [1]Zeitschrift fur Anorganische und Allgemeine Chemie,1997,vol. 623,p. 973 - 980

51
[ 85-01-8 ]
[ 1184-88-9 ]
[ 91-15-6 ]
[ 56666-55-8 ]
[ 68527-72-0 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 263 - 269

52
[ 1184-88-9 ]
[ 91-15-6 ]
[ 68527-72-0 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 263 - 269

53
[ 33252-26-5 ]
[ 91-15-6 ]
[ 1135680-60-2 ]

Reference： [1]Chemistry - A European Journal,2008,vol. 14,p. 10267 - 10279

54
[ 695-53-4 ]
[ 91-15-6 ]
[ 1310681-91-4 ]

Yield	Reaction Conditions	Operation in experiment
4.2%	With ammonium molybdate; urea; nickel dichloride; In quinoline; at 250℃; for 0.5h;Inert atmosphere;	(a) A mixture of 1 (0.10 g, 0.77 mmol), 2 (0.10 g, 0.77 mmol), anhydrous NiCl2 (0.1 g, 0.8 mmol), urea (0.09 g, 1.55 mmol), and a catalytic amount of MOA was stirred in quinoline (5 mL) at 250 C under argon for 30 min. After cooling to room temperature, the reaction mixture was diluted with 50% ethanol (50 mL). The resulting precipitate was filtered, and washed successively with hot water and hot 50% ethanol until the washings were colorless. The crude residue was transferred to a Soxhlet apparatus, and was extracted with toluene. The toluene solution was concentrated to approximately 5 mL under a reduced pressure, which was purified by silica gel column chromatography using toluene as eluent. The blue fraction was collected to give 6 mg of 3 (4.2%) after evaporation of the solvent. MASS (MALDI) (m/z): 553 (M++1). Anal Calcd for C29H18N8O1Ni: C, 62.96; H, 3.28; N, 20.26. Found: C, 62.69; H, 3.51; N, 19.95.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 2994 - 2996

55
[ 1953-99-7 ]
[ 91-15-6 ]
[ 433223-32-6 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation of Pigment A; Phthalonitrile (19.2g) and <strong>[1953-99-7]tetrachlorophthalonitrile</strong> (13.4g) were added to diethylene glycol (1 10g) and acetic acid (1 .7g). The reaction was heated to 140°C for 1 hour, cooled to 120°C and lithium acetate (3.8g) was added followed by triethylorthoacetate (21 ml) and anhydrous copper (II) chloride (7.4g). The reaction was stirred for 4 hours at 120°C, cooled to 80°C, and c HCI (20ml) was added.The reaction was stirred for a further 1 hour and then isopropanol (300ml) added.The solid which precipitated was filtered off and washed with hot water and isopropanol. The pigment was refluxed in isopropanol (500ml) and water (100ml), filtered while hot, washed with water and then acetone and dried to give the product (24g).

Reference： [1]Patent: WO2011/114130,2011,A1 .Location in patent: Page/Page column 13

56
[ 17132-78-4 ]
[ 1953-99-7 ]
[ 91-15-6 ]
copper dichloride [ No CAS ]
C₃₁H₁₁Cl₄CuN₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Phthalonitrile (12.8g), <strong>[1953-99-7]tetrachlorophthalonitrile</strong> (13.4g) and 2,3- dicyanopyridine(6.5g) were added to diethylene glycol (1 10g) and acetic acid (1 .7g). The reaction was heated to 140°C for 1 hour, cooled to 120°C and then lithium acetate (3.8g) was added followed by triethylorthoacetate (21 ml) and anhydrous copper(ll) chloride (7.4g). The reaction was stirred for 4 hours at 120°C, cooled to 80°C, and c-HCI (20ml) added. The reaction was stirred for a further 1 h and then isopropanol (300ml) was added. The precipitated solid was filtered off and washed with hot water and isopropanol. The pigment was refluxed in isopropanol (500ml) and water (100ml), filtered hot, washed with water and acetone and dried to give product (26g).

Reference： [1]Patent: WO2011/114131,2011,A1 .Location in patent: Page/Page column 13-14

57
[ 91-15-6 ]
[ 88-96-0 ]

Reference： [1]ChemSusChem,2012,vol. 5,p. 1392 - 1396
[2]ChemSusChem,2011,vol. 4,p. 104 - 111
[3]ChemCatChem,2018,vol. 10,p. 449 - 458

58
[ 17132-78-4 ]
[ 1953-99-7 ]
[ 91-15-6 ]
copper dichloride [ No CAS ]
C₃₁H₁₁Cl₄N₉^(2-)*Cu⁽²⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26 g		Preparation of Pigment A [0126] [0127] Phthalonitrile (12.8 g), <strong>[1953-99-7]tetrachlorophthalonitrile</strong> (13.4 g) and 2,3-dicyanopyridine(6.5 g) were added to diethylene glycol (110 g) and acetic acid (1.7 g). The reaction was heated to 140° C. for 1 hour, cooled to 120° C. and then lithium acetate (3.8 g) was added followed by triethylorthoacetate (21 ml) and anhydrous copper(II) chloride (7.4 g). The reaction was stirred for 4 hours at 120° C., cooled to 80° C., and c-HCl (20 ml) added. The reaction was stirred for a further 1 h and then isopropanol (300 ml) was added. The precipitated solid was filtered off and washed with hot water and isopropanol. The pigment was refluxed in isopropanol (500 ml) and water (100 ml), filtered hot, washed with water and acetone and dried to give product (26 g).

Reference： [1]Patent: US2013/11636,2013,A1 .Location in patent: Paragraph 0126; 0127

59
[ 5162-44-7 ]
[ 91-15-6 ]
4-(but-3-en-1-yl)phthalonitrile [ No CAS ]
[ 62170-45-0 ]

Reference： [1]Russian Journal of Organic Chemistry,2013,vol. 49,p. 138 - 144
Zh. Org. Khim.,2013,vol. 49,p. 142 - 148

60
[ 3333-52-6 ]
[ 91-15-6 ]
C₃₂H₂₆N₈ [ No CAS ]

Reference： [1]Journal of Porphyrins and Phthalocyanines,2013,vol. 17,p. 785 - 790

61
[ 91-15-6 ]
[ 32372-82-0 ]
2-(aminomethyl)benzonitrile hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%; 66%Spectr.		General procedure: To a 50 mL round-bottom flask, under nitrogen atmosphere, containing dinitriles 1p (500 mg, 4.2 mmol, 1.0 equiv) in 5.0 mL of toluene were added PMHS (1.0 mL, 16.8 mmol, 4.0 equiv) and Ti(Oi-Pr)4 (1.3 mL, 4.3 mmol, 1.0 equiv). The mixture was then heated at 100C for 24 h (the colorless solution turned into deep purple). After cooling to rt, the clear solution was diluted in toluene (30 mL) and hydrolyzed with aqueous 1M HCl (15 mL, 3.6 equiv) for 4 h (until the deep purple solution became yellow). The crude mixture was then concentrated under reduced pressure. The resulting solid was filtered, washed with pentane (60 mL), dissolved in chloroform and filtrate on a pad of Celite. The filtrate was finally concentrated under reduced pressure affording the amine 3p as a hydrochloride salt.

Reference： [1]Tetrahedron,2014,vol. 70,p. 975 - 983

62
[ 7446-70-0 ]
[ 631-61-8 ]
[ 91-15-6 ]
[ 14154-42-8 ]

Yield	Reaction Conditions	Operation in experiment
74.5%	at 200℃; for 12h;	Example 6 Synthesis of Chloroaluminum Phthalocyanine Pigments Using Ammonium Acetate Without the Use of a Heavy Metal Catalyst A chloroaluminum phthalocyanine pigment (Pigment 6) was synthesized using equal molar ratios of an ammonium salt, ammonium acetate (CH3COONH4), and aluminum(III) chloride (AlCl3), without using a heavy metal catalyst, according to the following procedure. 76.80 g phthalonitrile, 20.00 g anhydrous aluminum(III) chloride, 11.79 g ammonium acetate and 406.0 g dichlorotoluenes (isomer mixture) were added to a 1 L glass kettle. The reaction mixture was stirred as the temperature was raised to 200 C. over a period of one hour and maintained for a total of 11 hours at 200 C. before cooling to room temperature. After cooling, the solvent was removed by vacuum distillation to obtain a crude phthalocyanine reaction product. The crude phthalocyanine reaction product was purified by preparing a slurry in 2.5 L of 1% aqueous sulfuric acid and heating to 90 C. for two hours with stirring, followed by filtration at 90 C., washing with water until the filtrate was neutralized, and drying at 80 C. to obtain 64.21 g (74.5%) of a purified reaction product.

Reference： [1]Patent: US2014/179915,2014,A1 .Location in patent: Paragraph 0147; 0148

63
[ 7446-70-0 ]
[ 57-13-6 ]
[ 91-15-6 ]
[ 14154-42-8 ]

Yield	Reaction Conditions	Operation in experiment
99.26%	With ammonium molybdate; at 200℃; for 12h;	Example 2 Comparative Method-No Ammonium Salt A chloroaluminum phthalocyanine pigment (Pigment 2) was prepared by adding 153.6 g phthalonitrile, 40.00 g anhydrous aluminum(III) chloride, 32.00 g urea, 1.20 g ammonium dimolybdate and 812.0 g dichlorotoluenes (isomer mixture) to a 1 L glass kettle. The reaction mixture was stirred as the temperature was raised to 200 C. over a period of three hours and maintained for a total of nine hours at 200 C. before cooling to room temperature. After cooling, the solvent was removed by vacuum distillation to obtain a crude phthalocyanine reaction product. The crude phthalocyanine reaction product was purified by preparing a slurry in 1% aqueous sulfuric acid and heating to 90 C. for two hours with stirring, followed by filtration at 90 C., washing with water until the filtrate was neutralized, and drying at 80 C. to obtain a 99.26% yield of a purified reaction product.

Reference： [1]Patent: US2014/179915,2014,A1 .Location in patent: Paragraph 0133

64
[ 7446-70-0 ]
[ 7664-41-7 ]
[ 91-15-6 ]
[ 14154-42-8 ]

Yield	Reaction Conditions	Operation in experiment
85.37%	at 200℃; for 10.75h;	Example 3 Comparative Method-No Ammonium Salt A chloroaluminum phthalocyanine pigment (Pigment 3) was prepared by adding 76.8 g phthalonitrile, 20.00 g anhydrous aluminum(III) chloride and 406.0 g dichlorotoluenes (isomer mixture) to a 1 L glass kettle. The reaction mixture was stirred as ammonia gas was bubbled beneath the reaction surface as the temperature was raised to 200 C. over a period of 1.25 hours. Ammonia gas was continuously bubbled into the reaction mixture over the next two hours while the temperature was maintained at 200 C. After the bubbling of ammonia gas was discontinued, the reaction mixture was maintained at 200 C. for an additional 7.5 hours (10.75 hours at 200 C. total) before cooling to room temperature. After cooling, the solvent was removed by vacuum distillation to obtain a crude phthalocyanine reaction product. The crude phthalocyanine reaction product was purified by preparing a slurry in 2.5 L of 1% aqueous sulfuric acid and heating to 90 C. for two hours with stirring, followed by filtration at 90 C., washing with water until the filtrate was neutralized, and drying at 80 C. to obtain 73.57 g (85.37%) of a purified reaction product.

Reference： [1]Patent: US2014/179915,2014,A1 .Location in patent: Paragraph 0136

65
[ 7446-70-0 ]
[ 12125-02-9 ]
[ 91-15-6 ]
[ 14154-42-8 ]

Yield	Reaction Conditions	Operation in experiment
	at 200℃; for 10.5h;	Example 4 Synthesis of Chloroaluminum Phthalocyanine Pigments Using Ammonium Chloride Without the Use of a Heavy Metal Catalyst Several chloroaluminum phthalocyanine pigments were synthesized using varying molar ratios of ammonium chloride (NH4Cl) and aluminum(III) chloride (AlCl3) without using a heavy metal catalyst. Pigments 4A-4E were synthesized using 0.45:1, 0.9:1, 1:1, 1.8:1 and 3.6:1 molar equivalents of ammonium chloride to 53 aluminum(III) chloride, respectively, according to the following general procedure. Phthalonitrile, anhydrous aluminum(III) chloride, ammonium chloride and dichlorotoluenes (isomer mixture) were added to a 1 L glass kettle. The reaction mixture was stirred as the temperature was raised to 200 C. over a period of 1-1.5 hours and maintained for a total of 10.5 to 17 hours at 200 C. before cooling to room temperature. After cooling, the solvent was removed by vacuum distillation to obtain a crude phthalocyanine reaction product. The crude phthalocyanine reaction product was purified by preparing a slurry in 2.5 L of 1% aqueous sulfuric acid and heating to 90 C. for two hours with stirring, followed by filtration at 90 C., washing with water until the filtrate was neutralized, and drying at 80 C. to obtain a purified reaction product.

Reference： [1]Patent: US2014/179915,2014,A1 .Location in patent: Paragraph 0138; 0139; 0141

66
[ 7446-70-0 ]
ammonium sulfate [ No CAS ]
[ 91-15-6 ]
[ 14154-42-8 ]

Yield	Reaction Conditions	Operation in experiment
89.11 g	at 200℃; for 12h;	Example 5 Synthesis of Chloroaluminum Phthalocyanine Pigments Using Ammonium Sulfate Without the Use of a Heavy Metal Catalyst A chloroaluminum phthalocyanine pigment (Pigment 5) was synthesized using equal molar ratios of ammonium sulfate ((NH4)2SO4) and aluminum(III) chloride (AlCl3), without using a heavy metal catalyst, according to the following procedure. 76.80 g phthalonitrile, 20.00 g anhydrous aluminum(III) chloride, 19.80 g ammonium sulfate and 406.0 g dichlorotoluenes (isomer mixture) were added to a 1 L glass kettle. The reaction mixture was stirred as the temperature was raised to 200 C. over a period of two hours and maintained for a total of 10 hours at 200 C. before cooling to room temperature. After cooling, the solvent was removed by vacuum distillation to obtain a crude phthalocyanine reaction product. The crude phthalocyanine reaction product was purified by preparing a slurry in 2.5 L of 1% aqueous sulfuric acid and heating to 90 C. for two hours with stirring, followed by filtration at 90 C., washing with water until the filtrate was neutralized, and drying at 80 C. to obtain 89.11 g (103%) of a purified reaction product.

Reference： [1]Patent: US2014/179915,2014,A1 .Location in patent: Paragraph 0143; 0144

67
[ 6147-53-1 ]
[ 91-15-6 ]
[ 3317-67-7 ]

Yield	Reaction Conditions	Operation in experiment
87%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 135℃; for 3h;Inert atmosphere;	General procedure: In a two-necked 50 mL round bottom flask equipped with a reflux condenser and amagnetic stirrer, 1.0 g (1 eq) of phthalonitrile, 0.30 eq of hydrated salt and two Pasteurdrops(approx. 32 mg, 0.21 mmol, 0.027 eq) of DBU (or 0.21 eq of KOH) were added andstirred in 5 mL of solvent (or in a 5.5 g of anisole/glycerol mixture) under reflux for 3 h.The mixture was then cooled, treated with 15 mL of HCl 1N, filtered and washed withwater (2 x 20 mL) and methanol (2 x 15 mL). It was then purified in a Soxhlet extractorwith glacial acetic acid until the extracts were colorless.
84%	With butyl(2-hydroxyethyl)dimethylammonium acetate; at 100℃; for 2h;Ionic liquid; Inert atmosphere;	General procedure: A mixture of desired phthalonitrile (4a-i, 200mg) and corresponding metal salts (0.25 equivalents) were stirred at 100C with functional ionic liquid 2c (1 equivalent) for the appropriate time (Table 1, 2 and 3). The progress of the reaction was monitored by TLC and UV-Visible spectroscopic analysis. When reaction was completed, the mixture was cooled to room temperature, and distilled water (50 mL) was added to dissolve the functional ionic liquid. The blue-green solid mass was filtered and the aqueous filtrate was evaporated using reduced pressure to recover the pure ionic liquid for further use. The solid mass was further washed thoroughly with H2O-MeOH (1:1, 100 mL) to remove the colorless impurities and metallophthalocyanines are obtained in pure form. All of the phthalocyanines are known compounds and their purities were confirmed by UV-Visible spectroscopic analysis and further comparison with literature.

Reference： [1]Molecules,2021,vol. 26
[2]Synthetic Communications,2014,vol. 44,p. 2797 - 2807

68
[ 4387-36-4 ]
potassium ferrocyanide [ No CAS ]
[ 91-15-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 12h;	General procedure: F mixture of aryl halide (1.0 mmol), K4Fe(CN)6 (0.17 mmol), K2CO3 (1.0 mmol) and Pd/CuO NPs(0.024 mol percent) in DMF (5.0 mL) was heated at 120C for the appropriate time. After completion of the reaction, the mixture was cooled to room temperature and the catalyst separated from the reaction mixture using centrifuge. The resultant solution was extracted with Et2O (320 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure to give the crude product. The residue was purified by recrystallization using ethanol and water. The purity of the compounds was confirmed by 1H NMR.
42%	With 3% Pd/CeO2; sodium acetate; In N,N-dimethyl-formamide; isopropyl alcohol; at 65℃; for 10h;Irradiation;	0.25 mmol of 2-cyanoiodobenzene, 0 l of the cyanide reagent K4 [Fe (CN) 6] was added to a 25 mL screw test tube, Sodium acetate 0.25 mmol, 100 mg 3 wtpercent Pd / Ce ?, and then 7 mL of N, N-dimethylformamide and lmL isopropanol Organic solvent to test tube, 500W visible light irradiation under the magnetic stirring reaction, control visible light intensity of 0.74W / cm2, anti Should be the temperature of 65 ° C, 10 hours after the reaction to stop the reaction, take a small amount of reaction solution by microporous membrane filtration, methanol solvent dilution And the liquid sample to be tested, the sample to be tested with 2-cyanide iodobenzene standard, phthalonitrile standard for high-performance liquid phase detection comparison The selectivity of the reaction product was 94.1percent, the selectivity of the target product was 49.7percent, and the liquid product yield was 46.8percent. Rear Processing method for the use of cloth funnel filter washing catalyst, drying for recycling use; reaction solution by dichloromethane and water After the mixed solution was extracted, the organic layer was concentrated and the final product phthalonitrile was obtained by column chromatography. The isolated yield was 42percent

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 337 - 339
[2]RSC Advances,2015,vol. 5,p. 2785 - 2793
[3]Patent: CN105777579,2016,A .Location in patent: Paragraph 0052; 0053
[4]RSC Advances,2014,vol. 4,p. 57639 - 57645

69
[ 1095-03-0 ]
C₂₀H₂₂N₂ [ No CAS ]
[ 91-15-6 ]
C₄₂H₃₂BN₅O [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 7510 - 7514
Angew. Chem.,2015,vol. 127,p. 7620 - 7624,5

70
[ 1095-03-0 ]
C₁₆H₁₄N₂O [ No CAS ]
[ 91-15-6 ]
C₃₈H₂₄BN₅O₂ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 7510 - 7514
Angew. Chem.,2015,vol. 127,p. 7620 - 7624,5

71
[ 1095-03-0 ]
(Z)-1-(4-trifluoromethylphenylmethylene)-1H-isoindol-3-amine [ No CAS ]
[ 91-15-6 ]
C₃₈H₂₁BF₃N₅O [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 7510 - 7514
Angew. Chem.,2015,vol. 127,p. 7620 - 7624,5

72
[ 1095-03-0 ]
(Z)-1-(phenylmethylene)-1H-isoindol-3-amine [ No CAS ]
[ 91-15-6 ]
C₃₇H₂₂BN₅O [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 7510 - 7514
Angew. Chem.,2015,vol. 127,p. 7620 - 7624,5

73
[ 32703-80-3 ]
(4-(biphenyl-2-yloxy)-3,5,6-trichlorophthalonitrile) [ No CAS ]
[ 557-34-6 ]
[ 91-15-6 ]
C₄₈H₂₉Cl₃N₈OZn [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In pentan-1-ol;Reflux;	Of the compound represented by Formula 4 prepared in Synthesis Example 4 in 100mL flask precursor 4-(2-phenylphenoxy)-3,5,6-trichlorophthalonitrile (1.0g), 4-tert-butylphthalonitrile (0.46g), phthalonitrile (0.64g), 1,8-Diazabicycloundec-7-ene (1.9g), 1-pentanol, and come into the (20mL), then heated to dissolve the solid, and refluxed while putting the zinc acetate (0.46g) heating. After completion of the reaction remove the solvent, and purified by column chromatography. After the resulting solid into dichloromethane dissolved the solid was crystallized by addition of hexane. At this time, to the resulting solid by filtration and vacuum dried to obtain a compound represented by the formula (5).

Reference： [1]Patent: KR2015/127463,2015,A .Location in patent: Paragraph 0147-0148

74
vanadium(III) chloride [ No CAS ]
[ 69518-17-8 ]
[ 91-15-6 ]
C₃₂H₁₅IN₈OV [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6 g	With quinoline; at 150℃; for 10h;	3.9 g of B-4a and 2.5 g of B-4b were dissolved in quinoline, 2.4 g of VCl3 was added, and the mixture was stirred at 150 C for 10 hours.After cooling, water was added thereto and filtered to obtain 6.0 g of YA-4a.

Reference： [1]Patent: CN103052689,2016,B .Location in patent: Paragraph 0344-0349

75
[ 69316-08-1 ]
[ 91-15-6 ]
C₃₀H₁₉N₃O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		5.00 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 42.0 parts of methanolPart. While keeping it at 2 C,28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.)A mixture of 5.83 parts of methanol and 52.5 parts of methanol was added to the obtained mixture for 1 hourWas added dropwise over 30 minutes. The resulting mixture was stirred at 2 C. for 6 hours.While keeping the temperature at 4 C. or less, 7.59 parts of acetic acid was added to the obtained mixture,Further, <strong>[69316-08-1]methyl 4-cyanoacetylbenzoate</strong> (Synthesized according to the method described in JP-A 8-176154)17.4 parts and 682 parts of methanol were added.The resulting mixture was stirred at room temperature for 4 hours,And the mixture was stirred at 40 C. for 48 hours. The resulting mixture was added toAfter distilling off the solvent with a rotary evaporator,The resulting residue was purified by column chromatography,2.21 parts of the compound (Compound 139) represented by the formula (I-7) was obtained.
		5.00 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 42.0 parts of methanol were mixed. While maintaining the temperature at 2 C., a mixture of 5.83 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 52.5 parts of methanol was added to the obtained mixture over 1 hour 30 minutes Was added dropwise. The resulting mixture was stirred at 2 C. for 6 hours. While keeping the temperature at 4 C. or less, 7.59 parts of acetic acid was added to the obtained mixture, and further 17.4 parts of <strong>[69316-08-1]methyl 4-cyanoacetylbenzoate</strong> (synthesized according to the method described in JP-A 8-176154) And 682 parts of methanol were added. The resulting mixture was stirred at room temperature for 4 hours and then stirred at 40 C. for 48 hours. The obtained mixture was evaporated with a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 2.21 parts of a compound (Compound 139) represented by the formula (I-7).

Reference： [1]Patent: JP2017/137490,2017,A .Location in patent: Paragraph 1295; 1296
[2]Patent: JP2018/12834,2018,A .Location in patent: Paragraph 0370; 0371; 0372

76
[ 18853-32-2 ]
[ 98-54-4 ]
[ 10294-34-5 ]
[ 91-15-6 ]
[ 927177-49-9 ]
C₃₂H₂₁BCl₂N₆OS [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 16194 - 16198

77
[ 69518-17-8 ]
[ 10294-34-5 ]
[ 927-74-2 ]
[ 91-15-6 ]
C₂₈H₁₆BIN₆O [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 9809 - 9823

78
[ 2117-12-6 ]
[ 69518-17-8 ]
[ 10294-34-5 ]
[ 91-15-6 ]
C₃₁H₂₄BIN₆OSi [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 9809 - 9823

79
[ 69518-17-8 ]
[ 91-15-6 ]
C₅₆H₃₀B₂I₂N₁₂O₂ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 9809 - 9823

80
[ 91-15-6 ]
[ 88-96-0 ]
[ 17174-98-0 ]

Reference： [1]ChemCatChem,2018,vol. 10,p. 449 - 458

81
[ 98-54-4 ]
[ 69518-17-8 ]
[ 10294-34-5 ]
[ 91-15-6 ]
C₃₄H₂₄BIN₆O [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 2227 - 2234

82
[ 67-52-7 ]
[ 26391-06-0 ]
[ 91-15-6 ]
C₁₉H₁₇N₅O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		10.0 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 83 parts of methanol were mixed.A mixture of 11.7 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 105 parts of methanol was added dropwise to the resulting mixture while keeping the temperature at 2 to 5 for 1 hour and 30 minutes. The resulting mixture was stirred at 2 to 6 for 7 hours. 7.62 parts of acetic acid, 10.9 parts of 2-cyano-N, N-diethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 140 parts of methanol were added to the obtained mixture.Up to this point, 35 parts of methanol in total were added in addition to the above-described methanol.The obtained mixture was stirred at 65 for 3 days. To the obtained mixture, 3.82 parts of acetic acid and 5.48 parts of 2-cyano-N, N-diethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) were added and the mixture was stirred at 65 for 3 days. 7.65 parts of acetic acid, 10.0 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 363 parts of water were added to the obtained mixture, and the mixture was stirred at 65 for 9 days. The resulting mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain the compound represented by the formula IZ4-2.

Reference： [1]Patent: KR2018/26347,2018,A .Location in patent: Paragraph 2589-2593

83
[ 89942-45-0 ]
[ 91-15-6 ]

Reference： [1]ChemistryOpen,2018,vol. 7,p. 885 - 889

84
[ 91-15-6 ]
[ 3016-76-0 ]

Reference： [1]Patent: CN109678826,2019,A

85
[ 91-15-6 ]
[ 1107-00-2 ]

Reference： [1]Patent: CN109678826,2019,A

86
[ 91-15-6 ]
[ 212141-54-3 ]

Reference： [1]Patent: CN110204530,2019,A
[2]Patent: CN110204530,2019,A
[3]Patent: CN110204530,2019,A

87
[ 519059-09-7 ]
[ 91-15-6 ]
2-(4-fluoro-3-carboxyphenyl)acetylbenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94.4%		To a 500 ml four-necked flask equipped with a stirring, thermometer, reflux condenser and dropping funnel, 180 g of toluene, 13.0 g (0.1 mol) of phthalonitrile, 36.5 g (0.32 mol) of potassium tert-butoxide, between 50 and 55 C, a mixture of 16.0 g (0.1 mole) of <strong>[519059-09-7]4-fluoro-3-cyanobenzeneacetonitrile</strong> and 25 g of toluene was added dropwise. After the dropwise addition, the reaction was stirred at 75 to 80 C for 5 hours.Add 150 g of water and stir the reaction for 5 hours at 90 to 95 C. Cooled to 20 to 25 , layers were separated, the organic layer was washed with water and extracted 2 times 25 g of water, and the combined aqueous phase was acidified with 30% hydrochloric acid, pH of 2.0-2.5, filtered, washed with 10 g of water once, and dried to give 28.5 g of 2-(4-fluoro-3-carboxyphenyl)acetylbenzoic acid as a white solid with a yield of 94.4% and a liquid phase purity of 99.4%.

Reference： [1]Patent: CN110143945,2019,A .Location in patent: Paragraph 0098-0099; 0111-0112

88
[ 91-15-6 ]
[ 87-41-2 ]
[ 89942-45-0 ]

Reference： [1]Catalysis science and technology,2019,vol. 9,p. 6092 - 6101

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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

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 91-15-6 ] {[proInfo.proName]}

Quality Control of [ 91-15-6 ]

Related Doc. of [ 91-15-6 ]

Product Details of [ 91-15-6 ]

Safety of [ 91-15-6 ]

Application In Synthesis of [ 91-15-6 ]

[ 91-15-6 ] Synthesis Path-Upstream 1~16

[ 91-15-6 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 91-15-6 ]

Aryls

Nitriles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 91-15-6 ]