Name: 19606-98-5|N1,N1,N4-Triphenylbenzene-1,4-diamine|98%
Brand: Ambeed
SKU: A339155
Price: 22.0 USD
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1
[ 857468-42-9 ]
[ 19606-98-5 ]

Reference： [1]Chemische Berichte,1908,vol. 41,p. 3510

Yield	Reaction Conditions	Operation in experiment
75%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 10h;Inert atmosphere; Reflux;	General procedure: 2,4-dimethylaniline 2.67 g (molecular weight 121,22 mmol) was added to a 100 ml reaction flask under nitrogen.2.68 g of 2,4-dimethylbromobenzene (molecular weight 184,20 mmol), 5.76 g of sodium tert-butoxide (molecular weight 96,60 mmol),Pd2(dba)3 183 mg (molecular weight 916, 0.2 mmol), P(tBu)3 121 mg (molecular weight 202, 0.6 mmol).Anhydrous toluene 50 ml.After the addition, the oil bath was slowly heated to reflux reaction, and the reaction end was monitored by TLC, and the reaction was completed in 10 hours.Cooled, quenched with water, extracted with 50ml of dichloromethane, the organic phase dried over anhydrous MgSO4, the organic phase evaporated to dryness,The resulting solid was separated by column chromatography to give a white solid 3.8g, molecular weight 225, 85% yield.
75%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 10h;Inert atmosphere; Reflux;	General procedure: Under the protection of nitrogen, in 100 ml reaction flask is added 2,4-dimethylaniline 2.67 g (molecular weight 121,22 mmol), 2,4-dimethylbromo benzene 3.68 g (molecular weight 184, 20 mmol), sodium tert-5.76 g (molecular weight 96, 60 mmol), Pd2 (dba) 3 183 mg (molecular weight 916, 0.2 mmol), P (tBu) 3 121 mg (molecular weight 202, 0.6 mmol). Anhydrous toluene 50 ml. Canada finishes, the oil bath to be slowly heated to reflux reaction, TLC monitoring end point of the reaction, 10 hours of reaction. The cooling, water quenching reaction, for 50 ml dichloromethane extraction, the organic phase with anhydrous MgSO4 drying, the organic phase to dryness, the resulting solid method for the chromatographic separation, to obtain 3.8 g white solid, molecular weight 225, yield 85%.
71.9%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In cyclohexane; toluene; for 2h;Inert atmosphere; Reflux;	General procedure: Step 1: Synthesis of 3,5-dimethyl-N-phenylaniline (S2)Under nitrogen, in a 500ml three-necked round flask, add 15.7g (0.1mol) of bromobenzene, 13.3 g (0.11mol) 3,5-dimethylaniline, 0.57g (1.0mol%) Pd (dba)2 , 2.0 ml (1.0mol%) P(t-Bu)3 10% cyclohexane solution and 19.2g (0.2mol)NaO(t-Bu). Followed by addition of 250ml anhydrous toluene, to obtain a reaction solution. The said reaction solution under magnetic stirring in a 110deg.C oil bath was refluxed for 2h. Cool. Then the reaction solution was washed with water and an appropriate amount of 2-3 times after subjected to liquid separation, and the resulting organic phase was dried over anhydrous MgSO4, the organic solvent was removed by rotary evaporation to give crude product. The crude product was purified by silica gel (200-300 mesh, Qingdao Marine Chemical) column chromatography to give the product 16.1g, a yield of 81.6%.

With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene;Heating;

General procedure: After Sub 2-I-7 (15.6 g, 38.97 mmol) was dissolved in toluene (325 ml) in a round bottom flask, naphthalen-1-amine (CAS Registry Number: 134-32-7) (8.4 g, 58.45 mmol), Pd2(dba)3 (1.1 g, 1.17 mmol), 50% P(t-Bu)3 (1.5 ml, 3.12 mmol), NaOt-Bu (11.2 g, 116.91 mmol) were added the solution and the mixture was stirred at 100 C. When the reaction was completed, the reaction product was extracted with CH2Cl2 and water, and then the organic layer was dried with MgSO4 and concentrated. Then, the concentrate was applied to silica gel column and recrystallized to obtain 14.1 g (yield: 78%) of the product.

3
[ 64-17-5 ]
[ 857468-42-9 ]
sodium [ No CAS ]
[ 19606-98-5 ]

Reference： [1]Chemische Berichte,1908,vol. 41,p. 3510

4
[ 108-77-0 ]
[ 19606-98-5 ]
2,4,6-tris[N-[4-(diphenylamino)phenyl]-N-phenylamino]-1,3,5-triazine [ No CAS ]

Reference： [1]Organic Letters,2000,vol. 2,p. 171 - 174

5
[ 3132-99-8 ]
[ 19606-98-5 ]
[ 627538-91-4 ]

Reference： [1]Journal of Physical Chemistry A,2003,vol. 107,p. 9269 - 9283

6
[ 591-50-4 ]
[ 74-31-7 ]
[ 14118-16-2 ]
[ 19606-98-5 ]

Reference： [1]Organic Letters,2000,vol. 2,p. 171 - 174

7
[ 19606-98-5 ]
[ 87736-74-1 ]
N-[4-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-N,N',N'-triphenyl-benzene-1,4-diamine [ No CAS ]

Reference： [1]Macromolecules,2005,vol. 38,p. 1640 - 1647

8
diphenylnitrenium tetrafluoroborate [ No CAS ]
[ 122-39-4 ]
[ 19606-98-5 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 5283 - 5290

9
[ 122-39-4 ]
1-(N,N-diphenylamino)-2,4,6-trimethylpyridinium tetrafluoroborate [ No CAS ]
[ 19606-98-5 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 5283 - 5290

10
[ 36809-26-4 ]
[ 62-53-3 ]
[ 19606-98-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	With tri-tert-butyl phosphine; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 80℃; for 6h;Molecular sieve; Heating / reflux;	The reaction was conducted under the stream of argon. Into a 20 ml two-necked flask, 600 mg of molecular sieves 5A (adsorbing zeolite composed of crystalline sodium aluminosilicate; manufactured by Wako Pure Chemical Industries, Ltd.) was placed and stirred under heating under a reduced pressure sufficiently. To the above, 55 mg (the formula weight (FW): 915.70; 0.06 mmole) of Pd2(dba)3 (tris(dibenzylileneacetone) dipalladium(0)), 0.24 mmole (FW: 202.3; 89 µl as a 2.7 M toluene solution) of tBu3P, 807 mg (FW: 96.11; 8.4 mmole) of Na(OtBu) and 1.946 g (FW: 324.22; 6 mmole) of 4-bromophenyldiphenylamine were added. Then, 18.2 ml of toluene as the solvent was added, and the resultant mixture was sufficiently stirred. To the resultant mixture, 615 mg (FW: 93.129; 6.6 mmole) of aniline was added, and the reaction was allowed to proceed under the refluxing condition (about 80C) for 6 hours. The reaction product was filtered through Celite and sufficiently washed with ethyl acetate. The obtained product was purified in accordance with the silica gel column chromatography (the developing solvent: chloroform). As the result, 1.96 g (the yield: 97%) of the object product (N,N-diphenyl-N'-phenyl-p-phenylenediamine) was obtained (the Rf value: about 0.8). The obtained product was analyzed in accordance with the field desorption mass analysis (FD-MS), and the major ion peak was found at 336, which agreed with the calculated value.
91%	With caesium carbonate; triphenylphosphine; sodium t-butanolate; In toluene; at 80℃; for 8h;Inert atmosphere;	Under argon, the 4.66 g (50 mmol) aniline, 16.21 g (50 mmol) 4 - bromo-aniline, 9.. 61g (100 mmol) of sodium tert-butanol dissolved in 500 ml toluene in dehydration, stirring is added 0.23 g (1.0 mmol) of palladium acetate, 0.20 g (1.0 mmol) triphenylphosphine, in the 80 C lower reaction 8 hours. After cooling, the diatomite/silica gel funnel filter, the filtrate by reduced pressure distillation to remove the organic solvent, the obtained residue in toluene in the re-crystallization, drying, can get 15.31 g (45.5 mmol) intermediate A - 1, and the yield is 91%.
85%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; for 12h;Heating / reflux;	5) Synthesis of Material 7 (Formula 35); 4-bromo triphenylamine 7.6 g(23.45 mmol), aniline 21.85 g(0.235 mol), sodium tert-butoxide 6.76 g(70 mmol), Pd2(dba)3[(tris(dibenzilidene acetone)dipalladium(0))] 0.86 g(0.938 mmol) and tri(tert-butyl)phosphine 0.23 g(1.173 mmol) in 500 ml round bottom flask were dissolved with toluene 200 ml, and refluxed for 12 hours. After the reaction was terminated, the reaction solution was cooled to room temperature, and 200 ml of distilled water was added thereto to extract an organic layer. The organic layer was dried over MgSO4, concentrated, and purified by silica gel column chromatography. The eluate was concentrated and dried to give N,N,N'-triphenyl-p-phenylenediamine (6.71 g, 85%).The obtained N,N,N'-triphenyl-p-phenylenediamine (3.36 g, 10.0 mmol), compound 5 (2.0 g, 4.0 mmol), sodium tert-butoxide(1.15 g, 12 mmol), Pd2(dba)3[(tris(dibenzylidene acetone)dipalladium(0))] (0.14 g, 0.16 mmol) and tri(tert-butyl)phosphine (0.04 g, 0.2 mmol) in 100 ml round bottom flask were dissolved with 50 ml of toluene and refluxed for 12 hours. After the reaction was terminated, the reaction solution was cooled to room temperature and 50 ml of distilled water was added thereto to extract an organic layer. The obtained organic layer was dried over MgSO4, concentrated, and purified by silica gel column chromatography. The eluate was concentrated and dried to give material 7 represented by Formula 35 (2.91 g, yield: 72%).1H NMR (300 MHz, CDCl3, δ): 7.86-7.71(6H, m), 7.32-6.64 (m, 48H).

69%	With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In toluene; for 2h;Heating / reflux;	4-bromophenyl-N-phenyl-N-phenylamine (13.5 g, 41.6 mmol) and aniline (3.98 ml, 43.7 mmol) were dissolved in 120 ml of toluene, sodium-tertiary -butoxide (10.00 g, 104.1 mmol), bisdibenzylidene acetone palladium (0) (0.48 g, 0.83 mmol), and 50 wt% tri-tertiary-butylphosphine toluene solution (0.58 ml, 1.25 mmol) were added thereto, and reflux was conducted in a nitrogen atmosphere for 2 hours. Distilled water was added to the reaction solution to complete the reaction, and the organic layer was extracted. A column separation process was conducted using a solvent of n-hexane and tetrahydrofuran (n-hexane/THF = 10/1), stirring was conducted using petroleum ether, and vacuum drying was conducted to produce an arylamine connection group (9.6 g, yield 69%).[132] MS: [M+H]+= 336.
69%	With tri-tert-butyl phosphine; sodium t-butanolate;bis(dibenzylideneacetone)-palladium(0); In toluene; for 2h;Inert atmosphere; Reflux;	1) Production of arylamine (4-(N-phenyl-N-phenylamino)phenyl-1-phenylamine) to produce the compound represented by Formula 2-1-14-bromophenyl-N-phenyl-N-phenylamine (13.5 g, 41.6 mmol) and aniline (3.98 ml, 43.7 mmol) were dissolved in 120 ml of toluene, sodium-tertiary-butoxide (10.00 g, 104.1 mmol), bisdibenzylidene acetone palladium (0) (0.48 g, 0.83 mmol), and 50 wt % tri-tertiary-butylphosphine toluene solution (0.58 ml, 1.25 mmol) were added thereto, and reflux was conducted in a nitrogen atmosphere for 2 hours. Distilled water was added to the reaction solution to complete the reaction, and the organic layer was extracted. A column separation process was conducted using a solvent of n-hexane and tetrahydrofuran (n-hexane/THF=10/1), stirring was conducted using petroleum ether, and vacuum drying was conducted to produce an arylamine connection group (9.6 g, yield 69%).MS: [M+H]+=336.
65%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 90℃; for 12h;Inert atmosphere;	10 g of 4-bromo-N,N-diphenylaniline, 4.4 g of aniline,6 grams of sodium tert-butoxide, 0.8 grams of tris(dibenzylideneacetone)dipalladium(0),0.4 g of tri(tert-butyl)phosphine and 100 ml of toluene were placed in a 250 ml three-neck round bottom flask under a nitrogen atmosphere.And stirred at 90 C for 12 hours.The reaction solution was extracted with dichloromethane and concentrated, and then column chromatography using a mixed solvent of dichloromethane and n-hexane and concentration was performed, thus obtaining 6.6 g of N,N,N-triphenylbenzene-1,4-dichlorobenzene. Diamine (yield: 65%).
42%	With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In toluene; at 80℃; for 5h;Product distribution / selectivity;	formula 3Pd(dba)2, (f-Bu)3P f-BuONa, toluene(A-2)According to the foregoing reaction scheme (A-2), coupling the N,N-diphenyl-N-(4-bromophenyl)amine to aniline was carried out to synthesize N-(4-diphenylamino)phenylaniline which is an object of the present invention. Dehydrated toluene solution (5 ml) of N,N-diphenyl-N-(4-bromophenyl)amine (559 mg, 6 mmol), Pd (dba)2 (345 mg, 0.6 mmol), and t-BuONa (577 mg, 6mmol) was deaerated, and aniline (559 mg, 6 mmol) and P(t-Bu)3 (0.37 ml, 1.8 mmol) were added to the solution, then the mixture was heated to stir at 80 C under nitrogen atmosphere for 5 hours. Thin-layer chromatography confirmed that a raw material,4-bromotriphenylamine, was lost. The reaction was terminated by adding saturated salt solution and a water layer was extracted with approximately 100 ml of ethyl acetate. An organic layer was dried with magnesium sulfate and filtered. After condensing the filtrate, the filtrate was passed through silica gel column (ethyl acetate: hexane = 1: 20) to be purified. Then, an object as viscous fluid was obtained. The viscous fluid was added with hexane and exposed to ultrasound to separate cream-colored powder therefrom. The mixture was condensed to obtain the above mentioned compound N-(4-diphenylamino)phenylaniline in a yield of 42% based on the N,N-diphenyl-N-(4-bromophenyl)amine. FIG 1 shows a XH-NMR chart of the obtained N-(4-diphenylamino)phenylaniline and the result was as follows:*H NMR (300 MHz, CDC13) 5 ppm: 7.35-6.83 (m, 19H), 5.60 (s, 1H)FIG. 2 shows C-NMR chart of the N-(4-diphenylamino)phenylaniline and the result was as follows:13CNMR (75.5 MHz, DMSO-d6) 6 ppm: 147.8,143.7,140.2,139.4,129.4,129.3, 127.1,122.4,122.0,119.8,118.4,116.8The melting point of the obtained N-(4-diphenylamino)phenylaniline was measured by melting-point apparatus (manufactured by AS ONE CORPORATION, ATM-01) and the result was that the melting point was 105 to 106 C.FIG. 3 shows the result of thermogravimetry-differential thermal analysis (TG-DTA) of the N-(4-diphenylamino)phenylaniline. In FIG. 3, a left hand vertical axis represents calorie, whereas a right hand vertical axis represents weight (%; weight represented on the basis that the weight at onset of measurement as 100%). Further, a horizontal axis represents temperature (C). Thermo-Gravimetric/Differential Thermal Analyzer (SII Nano Technology Inc., TG/DTA-320) was used for the measurement, which measured thermophysical properties under nitrogen atmosphere at heating rate of 10 C/min. As a result, from the relationship between the weight and the temperature (thermogravimetry), the temperature at which the weight is 95% or less against the weight at the onset of measurement at normal pressure was 214 C.
42%	With tri-tert-butyl phosphine; sodium t-butanolate;bis(dibenzylideneacetone)-palladium(0); In hexane; toluene; at 80℃; for 5.05h;	A three-necked flask was charged with 559 mg (6 mmol) of 4-bromotriphenylamine, 345 mg (0.6 mmol) of dibenzylidineacetonepalladium (0), and 577 mg (6 mmol) of sodium tert-butoxide and the atmosphere in the flask was replaced by nitrogen. After that, 5 ml of dehydrated toluene was added to the flask including these, and degassing was carried out for about 3 minutes till air bubbles were not generated. 559 mg (6 mmol) of aniline, 0.37 ml (1.8 mmol) of tri-tert-buthylphosphine (10 % hexane solution) were added thereto, and stirring was carried out at 80 0C for 5 hours in an atmosphere of nitrogen. Then, it was confirmed by thin film chromatography (TLC) that 4-bromotriphenylamine as a material was almost gon&. A saturated aqueous solution of sodium chloride was added to finish the reaction, and a toluene layer and a water layer were obtained. The water layer was extracted with about 100 ml of ethyl acetate, and this ethyl acetate layer and the toluene layer ΛVere mixed. Magnesium sulfate was added to this mixed solution to remove moisture^ and then, the magnesium sulfate was removed by filtration. After concentrating this EPO <DP n="58"/>filtrate, an object was purified by silica gel column using a solvent of ethyl acetate and hexane in a ratio of 1:20. After purifying, further condensation was carried out, hexane was added, and the object was precipitated by using an ultra sonic washing machine. When the precipitation appeared, a condensation and a precipitation were carried out again and 700 mg of cream powder was obtained in a yield of 42 %.
42%	With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In hexane; toluene; at 80℃; for 5h;	(ii) Synthesis of N,N,N'-triphenyl-1,4-phenylenediamine (abbreviation: DPA); Subsequently, 0.56 g (6 mmol) of the 4-bromotriphenylamine obtained in (i) above, 0.35 g (0.6 mmol) of bis(dibenzylideneacetone)palladium(0), and 0.58 g (6 mmol) of sodium-tert-butoxide were put in a 100-mL three-neck flask, 5 mL of toluene was added therein, and nitrogen was substituted for air in the flask. Then, 0.56 g (6 mmol) of aniline and 0.37 mL (1.8 mmol) of a 10% hexane solution of tri-tert-butylphosphine were added therein, and the mixture was heated and stirred at 80 C. for 5 hours. After the reaction, the reaction was terminated by adding a saturated saline solution, and a water layer was extracted with approximately 100 mL of ethyl acetate. The extract was dried with magnesium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography of ethyl acetate:hexane=1:20; thus, 0.24 g of a light yellow powdered solid DPA that was an object of Step 2 was obtained (yield: 42%). The synthesis scheme of Step 2 as described above is shown in the following scheme (b-3).
42%	With tri-tert-butyl phosphine; sodium t-butanolate;bis(dibenzylideneacetone)-palladium(0); In toluene; at 80℃; for 5h;	A dehydrated toluene solution (5 mL) of 4-bromotriphenylamine (559mg, 6 mmol), Pd(dba)2 (345mg, 0.6 mmol), and t-BuONa (577 mg, 6 mmol) was degassed.Then, aniline (559 mg, 6 mmol) and P(t-Bu)3 (0 37 mL, 1.8 mmol) were added. The mixture was heated and stirred for 5 hours under a nitrogen atmosphere at 800C. By thin-film chromatography, it was ascertained that the raw material,4-bromotriphenylamine, had disappeared. A saturated saline solution was added to complete the reaction, and an aqueous layer was extracted with about 100 ml of ethyl acetate. The organic layer was dried by magnesium sulfate, and filtered. After the filtrate was concentrated, purification was conducted in an ethyl acetate:hexane = 120 silica gel column, and the target product was obtained as a viscous liquid. By adding hexane to this viscous liquid and applying ultrasonic waves, a cream-colored powder was extracted. This mixture was concentrated, and DPA was obtained in a yield of42%.[0282]1H NMR of the DPA obtained is shown: 1H NMR (300 MHz, CDCl3) δppm: 7.35 - 6.83 (m, 19H), 5 60 (s, IH) [0283]Further, the 13C NMR is shown: 13C-NMR (75.5 MHz, DMSO-d6) δ ppm: 147.8, 143.7, 140.2, 139.4, 129.4, 129.3, 127.1, 122.4, 122.0, 119.8, 118.4, 116.8 [0284]Next, a synthesis scheme (b-2) of DPA is shown.
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In toluene; at 90℃;Inert atmosphere;	Catalyst B was added to the solution of I (8.5 g, 26.2 mmol), aniline (7.34 g, 78.7 mmol) and sodium tert-butoxide (3.12 g, 32 mmol) in toluene (65 mL) and the mixture was stirred overnight at 90C under an argon atmosphere. The reaction was stopped by opening the reaction to the air and the insoluble material was removed by filtration. The product was purified by flash-column chromatography using toluene as the eluent.

Reference： [1]Patent: EP1749823,2007,A1 .Location in patent: Page/Page column 29-30
[2]Patent: CN108863918,2018,A .Location in patent: Paragraph 0081-0083
[3]Patent: US2007/290610,2007,A1 .Location in patent: Page/Page column 19
[4]Macromolecules,2005,vol. 38,p. 1640 - 1647
[5]Patent: WO2008/66358,2008,A1 .Location in patent: Page/Page column 48
[6]Patent: US2010/65828,2010,A1 .Location in patent: Page/Page column 116
[7]Patent: TWI602799,2017,B .Location in patent: Paragraph 0135-0136
[8]Patent: WO2006/16684,2006,A1 .Location in patent: Page/Page column 7-8
[9]Patent: WO2006/43647,2006,A1 .Location in patent: Page/Page column 55-56
[10]Patent: US2007/149784,2007,A1 .Location in patent: Page/Page column 70
[11]Patent: WO2007/43354,2007,A1 .Location in patent: Page/Page column 83-84
[12]Patent: WO2006/46441,2006,A1 .Location in patent: Page/Page column 77
[13]Patent: WO2006/114921,2006,A1 .Location in patent: Page/Page column 64-66
[14]Chemical Papers,2016,vol. 70,p. 1238 - 1252
[15]Organometallics,2017,vol. 36,p. 2692 - 2701

11
[ 19606-98-5 ]
[ 201731-79-5 ]
9,10-diphenyl-2-[N-(4-diphenylaminophenyl)-N-phenylamino]anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In hexane; toluene; at 80℃; for 6h;	[Step 2] Synthetic method of 2DPAPA.A synthetic scheme of 2DPAPAiS shown in (C-4). [0283] <n="135"/>(C-4) [0284] . . ;1.8 g (4.40 mmol) of 2-bromo-9,10-diphenylanthracene synthesized in Step 1 ofEmbodiment 1, 1.78 g (5.28 mmol) of iVJiV^Vri-triphenyl-i,4-pheϖylenediamiiie (DPA), 0.126 g (0.220 mmol) of bis(dibenzylideneacetone)palladium (0), and 2.11 g (21.99 mmol) of sodium tert-butoxide were put into a 100 mL three-neck flask, and the atmosphere in the flask was substituted with nitrogen. Further, 30 mL of toluene and0.44 g (0.220 mmol) of tri(fert-butyl)phosphine (a 10% hexane solution) were added to the flask, and the solution was heated at 80 0C for 6 hours. After the reaction, the solution was washed with water, and the aqueous layer was extracted with ethyl acetate.The organic layer was dried over magnesium sulfate, filtered and concentrated, and the residue was dissolved in toluene, which was followed by filtration through celite, Florisil, and then alumina. The filtrate was concentrated, and then the residue was recrystallized with chloroform, methanol, and hexane, resulting in 2.24 g of the target compound as a yellow solid in 77% yield. By a nuclear magnetic resonance measurement (NMR), it was confirmed that this compound was9,10-diphenyl-2-[iV-(4-diphenylaminophenyl)-iV-phenylamino]anthracene (abbreviation:2DPAPA). [0285]1H NMR data of 2DPAPA is shown below. 1H NMR (DMSO-J6, 300 MHz): δ = 6.90-7.14 (m, 15H), 7.25-7.37 (m, 10H), 7.44-7.52 (m, 8H), 7.57-7.66 (m, 3H). The 1H NMR chart is shown in FIGS. HA and HB. Note that the range of 6.5 ppm to 8.0 <n="136"/>ppm in FIG. 11 A is expanded and shown in FIG. HB. [

Reference： [1]Patent: WO2007/125934,2007,A1 .Location in patent: Page/Page column 132-134

12
[ 474688-77-2 ]
[ 19606-98-5 ]
N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In hexane; toluene; at 80℃; for 7h;	Synthetic method of 2DPABPhA.A synthetic scheme of 2DPABPhA is shown in (C-Il). [0320](C-11) [0321]2.0 g (3.56 mmol) of 9,10-di(2-biphenylyl)-2-bromoanthracene synthesized in Step 1 of Embodiment 3, 1.44 g (4.27 mmol) of iV^,λP-triphenyl-l,4-phenylenediamine (DPA), 0.102 g (0.178 mmol) of bis(dibenzylideneacetone)palladium (0), and 1.71 g (17.81 mmol) of sodium tert-butoxide were put into a 100 mL three-neck flask, and the atmosphere in the flask was substituted with nitrogen. 30 mL of toluene and 0.36 g (0.178 mmol) of tri(tert-butyl)phosphine (10% hexane solution) were added to the flask, and the solution was heated at 80 0C with stirring for 7 hours. After the reaction, the solution was washed with water, and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated, and the residue was dissolved in toluene. This toluene solution was filtered through celite, <n="146"/>Florisil, and then alumina. The filtrate was concentrated, and the residue was recrystallized with chloroform and methanol, giving 2.5 g of the target compound as a yellow solid in 87% yield. By the nuclear magnetic resonance measurement (NMR), it was confirmed that this compound was 9,10-di(2-biphenylyl)-2-[iV-(4-diphenylaminophenyl)-iV-phenylamino]anthracene (abbreviation: 2DPABPhA). [0322]The 1H NMR data of this compound is shown below. 1H-NMR (CDCl3, 300 MHz): δ = 6.78-7.08 (m, 24H), 7.12-7.30 (m, 10H), 7.32-7.59 (m, 10H). The 1H NMR chart is shown in each of FIGS.24A and 24B. Note that the range of 6.5 ppm to 8.0 ppm in FIG. 24A is expanded and shown in FIG. 24B. [0323]The decomposition temperature (Td) of 2DPABPhA, measured with a thermogravimetric/differential thermal analyzer (type TG/DTA 320, manufactured by Seiko Instruments Inc.), was found to be 419.8 C, meaning high thermal stability of this compound.

Reference： [1]Patent: WO2007/125934,2007,A1 .Location in patent: Page/Page column 143-144

13
[ 960135-41-5 ]
[ 19606-98-5 ]
C₇₅H₅₄N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; for 12h;Heating / reflux;	5) Synthesis of Material 7 (Formula 35); 4-bromo triphenylamine 7.6 g(23.45 mmol), aniline 21.85 g(0.235 mol), sodium tert-butoxide 6.76 g(70 mmol), Pd2(dba)3[(tris(dibenzilidene acetone)dipalladium(0))] 0.86 g(0.938 mmol) and tri(tert-butyl)phosphine 0.23 g(1.173 mmol) in 500 ml round bottom flask were dissolved with toluene 200 ml, and refluxed for 12 hours. After the reaction was terminated, the reaction solution was cooled to room temperature, and 200 ml of distilled water was added thereto to extract an organic layer. The organic layer was dried over MgSO4, concentrated, and purified by silica gel column chromatography. The eluate was concentrated and dried to give <strong>[19606-98-5]N,N,N'-triphenyl-p-phenylenediamine</strong> (6.71 g, 85%).The obtained <strong>[19606-98-5]N,N,N'-triphenyl-p-phenylenediamine</strong> (3.36 g, 10.0 mmol), compound 5 (2.0 g, 4.0 mmol), sodium tert-butoxide(1.15 g, 12 mmol), Pd2(dba)3[(tris(dibenzylidene acetone)dipalladium(0))] (0.14 g, 0.16 mmol) and tri(tert-butyl)phosphine (0.04 g, 0.2 mmol) in 100 ml round bottom flask were dissolved with 50 ml of toluene and refluxed for 12 hours. After the reaction was terminated, the reaction solution was cooled to room temperature and 50 ml of distilled water was added thereto to extract an organic layer. The obtained organic layer was dried over MgSO4, concentrated, and purified by silica gel column chromatography. The eluate was concentrated and dried to give material 7 represented by Formula 35 (2.91 g, yield: 72%).1H NMR (300 MHz, CDCl3, δ): 7.86-7.71(6H, m), 7.32-6.64 (m, 48H).

Reference： [1]Patent: US2007/290610,2007,A1 .Location in patent: Page/Page column 19

14
[ 13716-12-6 ]
[ 36809-26-4 ]
[ 865-48-5 ]
[ 19606-98-5 ]

Yield	Reaction Conditions	Operation in experiment
	With aniline;dipalladiumtris(benzylideneacetone); In toluene;	(2) Synthesis of N,N,N'-triphenyl-1,4-phenylenediamine A 0.66 weight % toluene solution 150 μl of tri-t-butylphosphine was added to a toluene 50 ml solution of 4-bromo-triphenylamine 5.00 g, aniline 1.72 g, tris(benzylideneacetone)dipalladium (0) 282 mg and t-butoxysodium 2.07 g, and the mixture was stirred at room temperature for 5 hours. After finishing the reaction, the mixture was filtered through celite, and the filtrate was extracted with toluene. This was concentrated under reduced pressure, and the resulting crude product was subjected to column refining to obtain 4.20 g of pale yellow powder of N,N,N'-triphenyl-1,4-phenylenediamine.

Reference： [1]Patent: US2006/232198,2006,A1

15
[ 603-34-9 ]
[ 19606-98-5 ]

Reference： [1]Macromolecules,2005,vol. 38,p. 1640 - 1647
[2]Chemical Papers,2016,vol. 70,p. 1238 - 1252
[3]Patent: JP5648101,2015,B2

16
[ 19606-98-5 ]
[ 849146-77-6 ]

Reference： [1]Macromolecules,2005,vol. 38,p. 1640 - 1647

17
[ 19606-98-5 ]
[ 849146-81-2 ]

Reference： [1]Macromolecules,2005,vol. 38,p. 1640 - 1647

18
[ 19606-98-5 ]
[ 627538-92-5 ]

Reference： [1]Journal of Physical Chemistry A,2003,vol. 107,p. 9269 - 9283

19
[ 19606-98-5 ]
(E,E,E)-4-[4-{4-[N-(4-diphenylaminophenyl)-N-(phenyl)-3-aminostyryl]-2,5-bis[(S)-2-methylbutoxy]styryl}-2,5-bis[(S)-2-methylbutoxy]styryl]-2,5-bis[(S)-2-methylbutoxy]-5-deuteriobenzene [ No CAS ]

Reference： [1]Journal of Physical Chemistry A,2003,vol. 107,p. 9269 - 9283

20
[ 19606-98-5 ]
(E,E,E)-4-[4-{4-[N-(4-diphenylaminophenyl)-N-(phenyl)-3-aminostyryl]-2,5-bis[(S)-2-methylbutoxy]styryl}-2,5-bis[(S)-2-methylbutoxy]styryl]-2,5-bis[(S)-2-methylbutoxy]benzaldehyde [ No CAS ]

Reference： [1]Journal of Physical Chemistry A,2003,vol. 107,p. 9269 - 9283

21
[ 632-52-0 ]
[ 19606-98-5 ]

Reference： [1]Chemische Berichte,1908,vol. 41,p. 3510

22
[ 29558-77-8 ]
[ 19606-98-5 ]
[ 896427-54-6 ]

Yield	Reaction Conditions	Operation in experiment
45%	With lithium hexamethyldisilazane;tris-(dibenzylideneacetone)dipalladium(0); CyJohnPhos; In 1,4-dioxane; toluene; at 80℃; for 72h;	A mixture of <strong>[29558-77-8]4-bromo-4'-hydroxybiphenyl</strong> (13.45 g, 5.3x10'2 mol) and [4-(N, N- diphenylamino)phenyl]phenylamine (20 g, 5.9x10"2 mol) in toluene (100 mL) and dioxane (100 ml_ ) are stirred under nitrogen. To this solution Pd2(dba)3 (0.970 g, 1.05x10"3 mol) and P(cyclohexyl)2(2-biphenyl) (0.890 g, 2.5x10"3 mol) are added followed by LiN(SiMe3)2 (19.8 g, 1.19x10'2 mol). The resulting mixture is heated at 800C for 72 hrs. After cooling to room temperature, 1 M HCl (50mL) is added and allowed to stir to 10 minutes. After neutralization with 10% NaHCO3 the phases are separated and the organic phase washed with water (2x200mL). The organic phase is dried over magnesium sulphate and the solvent is evaporated. Upon addition of hexane a brown solid is obtained which is further purified by chromatography (1 :5 EtOAc:hexane) to obtain a light-brown solid in 45% yield (12 g). The product was confirmed by NMR analysis.

Reference： [1]Patent: WO2006/72002,2006,A2 .Location in patent: Page/Page column 19-20

23
[ 29344-72-7 ]
[ 19606-98-5 ]

Yield	Reaction Conditions	Operation in experiment
83%	With sodium hydroxide; In tetrahydrofuran; ethanol; water; at 20℃; for 2h;Heating / reflux;Product distribution / selectivity;	Subsequently, the synthesized N-(4-diphenylamino)phenylacetanilide (20.00 g, 0.053 mol), 100 g of 40% sodium hydroxide solution, 50 ml of tetrahydrofuran, and 50 ml of ethanol are heated to be refluxed for 2 hours in the air. After the reaction, the solution was cooled to room temperature, and a water layer and an organic layer were isolated. The organic layer was washed with water twice. On the other hand, the water layer was extracted with chloroform twice. The chloroform layer and the organic layer were washed with saturated salt solution. After drying the chloroform layer and the organic layer with magnesium sulfate, the layers were filtered naturally and condensed to give a colorless solid. The obtained colorless solid was recrystallized with ethyl acetate-hexane and 14.69 g of colorless powder solid was obtained in a yield of 83%. 1H-NMR of the white powder solid was carried out to confirm that the white powder solid was N-(4-diphenylamino)phenylaniline.
83%	With sodium hydroxide; In tetrahydrofuran; ethanol; water; for 2h;Reflux;	To 500ml eggplant flask, synthesized N-(4- diphenylamino) phenyl acetanilide 20.00g (0.053mol), 40% aqueous sodium hydroxide solution 100 g, was refluxed in tetrahydrofuran 50 ml, 2 hours in the air put ethanol 50 ml. After completion of the reaction, to remove the aqueous sodium hydroxide after cooling to room temperature. The organic layer was washed twice with water, the aqueous layer was extracted twice with chloroform, washed with saturated saline together with the organic layer. After drying with magnesium acid, gravity filtered, and concentrated to a colorless solid with ethyl acetate thus obtained to give a colorless powdery solid was recrystallized 14.69g, 83% yield hexane. By a nuclear magnetic resonance method (1H-NMR), it was confirmed that this colorless powdery solid is N-(4- diphenylamino) phenyl aniline.

Reference： [1]Patent: WO2006/16684,2006,A1 .Location in patent: Page/Page column 11
[2]Patent: JP5648101,2015,B2 .Location in patent: Paragraph 0118; 0120-0121

24
[ 591-50-4 ]
[ 74-31-7 ]
[ 19606-98-5 ]

Yield	Reaction Conditions	Operation in experiment
65%		A mixture of N,N0-diphenyl-p-phenylenediamine (260 mg,1 mmol), [Pd(dppf)Cl2] (3.65 mg, 0.05 mmol), sodium tert-butoxide(144 mg, 1.5 mmol), toluene (10 ml) was stirred at 112 C for 5 minunder the protection of nitrogen, iodobenzene (1.2 mmol) wasthen added to the flask via a syringe. Then the reaction mixturewas kept at this temperature for 5 h. After cooled to room temperature,water (3 ml) and ethyl acetate (20 ml) was added to the mixture.The organic layer was separated from the aqueous layerthrough a separation funnel, and washed successively with waterand brine solution. After dried over anhydrous magnesium sulfatefor overnight, the solvents were evaporated under reduced pressure.The residue was purified by column chromatography on silicagel with chloroform/petroleum (v/v = 2:1) as eluent. Compound 5was collected as green powder (210.4 mg, 65%). MS (ESI): m/z, calculatedfor C24H20N2: 336.43, found: 336.11 [M+]. Elemental analysis(%), calculated for C24H20N2: C 78.60, H 5.94, N 8.32; found: C78.47, H 6.12, N 8.45.

Reference： [1]Journal of Molecular Structure,2014,vol. 1056-1057,p. 339 - 346
[2]Organic Letters,2011,vol. 13,p. 2826 - 2829
[3]Patent: WO2006/49316,2006,A1 .Location in patent: Page/Page column 18

25
[ 523-27-3 ]
[ 19606-98-5 ]
9,10-bis[N-(4-diphenylaminophenyl)-N-phenylamino]anthracene [ No CAS ]

Reference： [1]Patent: WO2006/49316,2006,A1 .Location in patent: Page/Page column 20

26
[ 19606-98-5 ]
[ 23055-77-8 ]
[ 885684-34-4 ]

Reference： [1]Patent: WO2006/46441,2006,A1 .Location in patent: Page/Page column 77; 78

27
[ 83-53-4 ]
[ 19606-98-5 ]
1,4-bis[N-(4-diphenylaminophenyl)-N-phenylamino] naphthalene [ No CAS ]

Reference： [1]Patent: WO2006/49316,2006,A1 .Location in patent: Page/Page column 18-19

28
[ 19606-98-5 ]
[ 57103-21-6 ]
3,6-bis[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With tri-tert-butyl phosphine; sodium t-butanolate;bis(dibenzylideneacetone)-palladium(0); In hexane; toluene; at 80℃; for 16.05h;Microwave irradiation;	A three-necked flask was charged with 5.44 g (11 mmol) of 3,6-diiodo-9-phenylcarbazol, 9 g (27 mmol) ofN-(4-diphenylaminophenyl)-N-phenylamine, 500 mg (0.87 mmol) of dibenzylideneacetonepalladium, and 3.35 g (35 mmol) of sodium tert-butoxide and the atmosphere in the flask was replaced by nitrogen. 100 ml of dehydrated toluene was added thereto and degassing was carried out for 3 minutes. After adding 4 ml of tri-tert-butylphosphine (10 wpercent hexane solution), the solution was stirred for 16 hours at 80 0C in an atmosphere of nitrogen. After the reaction, a saturated aqueous solution of sodium chloride was added and the solution was extracted with 200 ml of ethyl acetate. Magnesium sulfate was added thereto to remove moisture. Then, the solution was filtered to remove magnesium sulfate. The filtrate was condensed and was added by drops to a solution of ethyl acetate and hexane in a ratio of 1:10 to be suspended. Supernatant liquid of the suspension was collected. Then the collected supernatant liquid was purified by silica gel column with the solvent of ethyl acetate and hexane in a ratio of 1:10 and was condensed to obtain cream-colored powder. Insoluble constituent of the suspension was purified using solvent of toluene and hexane in a ratio of 5:1 by a silica gel column to obtain cream-colored powder. Thus obtained cream-colored powder is the object and was 6.5 g in a yield of 75 percent in total. The NMR data of the object are indicated below. 1H NMR (300MHz, DMSO-d); 6=6.86-6.97 (m, 26H), 7.18-7.36 (m, 14H), 7.35 (d, j=9.0, 2H), 7.52-7.66 (m 5H), 7.99 (s, 2H). FIG. 15 shows a chart of 1H NMR and FIG. 16 shows an enlarged view of the portion from 6.0 to 9.0 ppm in FIG. 15.

Reference： [1]Patent: WO2006/43647,2006,A1 .Location in patent: Page/Page column 60-61

29
[ 19606-98-5 ]
[ 502161-03-7 ]
3-[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With tri-tert-butyl phosphine; sodium t-butanolate;bis(dibenzylideneacetone)-palladium(0); In hexane; toluene; at 80℃; for 0.216667h;Microwave irradiation;	627.64 mg (1.7 mmol) of 3-iodine-9-phenylcarbazol, 672.86 mg (2.0 mmol) of N-(4-diphenylaminophenyl)-N-phenylamine, 57.5 mg (0.1 mmol) of dibenzylideneacetonepalladium, and 335 mg (3.5 mmol) of sodium tert-butoxide were put into a three-necked flask, and the atmosphere in the flask was replaced by nitrogen. 3.5 ml of dehydrated toluene was added thereto and degassing was carried out for 3 minutes. After adding 0.4 ml of tri-tert-butylphosphine (10 w% hexane solution), the flask was shaked lightly up and down to stir the content. The solution was heated and stirred at 80 0C for 10 minutes with irradiating by a microwave at 200 W. After the reaction, saturated aqueous solution of sodium chloride was added, and the extraction with 100 ml of ethyl acetate was carried out. Further, magnesium sulfate was added to remove moisture, and then, magnesium sulfate was removed by filtration. Filtrate was EPO <DP n="60"/>condensed and purified by silica gel column using a solution of ethyl acetate and hexane in a ratio of 1:1. Hexane was added to the purified solution, and recrystallization was carried out to obtain 650 mg of cream powder in a yield of 65 %. The NMR data are indicated below. 1H NMR (300MHz, DMSO-d); delta=6.89-7.05 (m, 13H), 7.21-7.28 (m, 9H), 7.32-7.43 (m, 3H), 7.50-7.69 (m, 5H), 8.02(s, IH), 8.14 (d, j=7.2, 1 H). In addition, FIG. 13 shows a chart of 1H NMR, and FIG. 14 shows an enlarged view of the porition of 6.0 to 9.0 ppm in FIG. 13.

Reference： [1]Patent: WO2006/43647,2006,A1 .Location in patent: Page/Page column 57-58

30
[ 885684-37-7 ]
[ 19606-98-5 ]
C₆₉H₅₄N₄ [ No CAS ]

Reference： [1]Patent: WO2006/46441,2006,A1 .Location in patent: Page/Page column 81

31
[ 885684-41-3 ]
[ 19606-98-5 ]
C₇₂H₅₈N₄ [ No CAS ]

Reference： [1]Patent: WO2006/46441,2006,A1 .Location in patent: Page/Page column 84

32
[ 19606-98-5 ]
[ 668493-37-6 ]
C₅₄H₄₁N₃ [ No CAS ]

Reference： [1]Patent: WO2006/114921,2006,A1 .Location in patent: Page/Page column 64-66

33
[ 19606-98-5 ]
[ 148231-12-3 ]
5,8-bis[{4-(diphenylamino)phenyl}phenylamino]quinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With tri-tert-butyl phosphine; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 120℃; for 6h;Molecular sieve; Heating / reflux;	The reaction was conducted under the stream of argon. Into a 20 ml two-necked flask, 600 mg of molecular sieves 5A was placed and stirred under heating under a reduced pressure sufficiently. To the above, 48.4 mg (FW: 915.70; 0.0528 mmole) of Pd2(dba)3, 0.212 mmole (FW: 202.3; 78.6 mul as a 2.7 M toluene solution) of tBu3P, 710 mg (FW: 96.11; 7.39 mmole) of Na(OtBu) and 1.96 g (FW: 33.644; 5.82 mmole) of N,N-diphenyl-N'-phenyl-p-phenylenediamine were added. Then, 16 ml of toluene as the solvent was added, and the resultant mixture was sufficiently stirred. To the resultant mixture, 767 mg (FW: 289.94; 2.64 mmole) of <strong>[148231-12-3]5,8-dibromoquinoxaline</strong> was added, and the reaction was allowed to proceed under the refluxing condition (about 120C) for 6 hours. The reaction product was filtered through Celite and sufficiently washed with ethyl acetate. The obtained product was purified in accordance with the silica gel column chromatography (the developing solvent: methylene chloride). As the result, 1.74 g (the yield: 83%) of the object product (Compound (1)) was obtained (the Rf value: about 0.5). The obtained product was analyzed in accordance with FD-MS, and the major ion peak was found at 798, which agreed with the calculated value. The glass transition temperature as measured in accordance with the differential scanning calorimetry (DSC) was 138.6C, and the ionization potential was 5.3 eV.

Reference： [1]Patent: EP1749823,2007,A1 .Location in patent: Page/Page column 30-31

34
[ 21510-43-0 ]
[ 19606-98-5 ]
2-{4-[N-(4-diphenylaminophenyl)-N-phenylamino]phenyl}-5-phenyl-1,3,4-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In hexane; toluene; at 80℃; for 8h;	Step 3: Synthesis of 2-{4-[N-(4-diphenylaminophenyl)-N-phenylamino]phenyl}-5-phenyl-1,3,4-oxadiazole (abbreviation: DPAO11); 0.61 g (2.0 mmol) of O11Br obtained in Step 1, 0.67 g (2.0 mmol) of DPA obtained by the method shown in Step 2, 1.0 g (10.4 mmol) of sodium-tert-butoxide, and 0.014 g (0.02 mmol) of bis(dibenzylideneacetone)palladium(0) were put in a 50-mL three-neck flask, and nitrogen was substituted for air in the flask. Then, 7 mL of toluene and 0.1 mL of a 10% hexane solution of tri-tert-butylphosphine were added therein, and the mixture was heated and stirred at 80 C. for 8 hours. After the reaction was terminated, an obtained solid was dissolved in chloroform, washed with water and a saturated saline solution in this order, and filtered through Celite. The filtrate was concentrated, and an obtained solid was dissolved in toluene and purified by silica gel column chromatography. Purification by column chromatography was performed by using toluene as a developing solvent and then using a mixed solvent of toluene:ethyl acetate=1:1 as a developing solvent. The purified solid was recrystallized with chloroform and hexane; thus, 0.65 g of a yellow solid DPAO11 that was an object of Synthesis Example 3 was obtained (yield: 58%). The synthesis scheme of Step 3 as described above is shown in the following scheme (c-3). The following shows a result of analyzing DPAO11 that was obtained in Step 3 by nuclear magnetic resonance spectroscopy (1H-NMR). FIG. 12A shows an 1H-NMR chart and FIG. 12B shows an enlarged chart thereof. Accordingly, it was found that the oxadiazole derivative DPAO11 of the present invention represented by the structural formula (91) was obtained in Synthesis Example 3. 1H-NMR (CDCl3, 300 MHz,): δ=7.00-7.37 (m, 21H), δ=7.52 (m, 3H), δ=7.95 (d, J=9.0, 2H), δ=8.10-8.13(m, 2H) Next, the absorption spectrum and the emission spectrum of DPAO11 were measured. The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V-550, by JASCO Corporation) and the emission spectrum was measured using a spectrofluorometer (FS920, by Hamamatsu Photonics K.K.). The measurement was performed at room temperature for a toluene solution and a deposited film. FIG. 13A shows a measurement result for the toluene solution and FIG. 13B shows a measurement result for the deposited film. The horizontal axis indicates the wavelength and the vertical axis indicates the intensity of the absorption and light emission. As shown in FIG. 13A, the oxadiazole derivative DPAO11 of the present invention has an absorption peak at 369 nm with the toluene solution. A reference numeral 1300a is an absorption spectrum. In addition, the emission spectrum 1300b has a peak at 498 nm. Note that the emission spectrum was measured through excitation of DPAO11 at a wavelength of 369 nm. In addition, as shown in FIG. 13B, the deposited film of the oxadiazole derivative DPAO11 of the present invention has an absorption peak at 373 nm. A reference numeral 1301a is an absorption spectrum. In addition, the emission spectrum 1301b has a peak at 504 nm. Note that the emission spectrum was measured through excitation of DPAO11 at a wavelength of 373 nm. Data on the absorption spectrum in FIG. 13B was used to obtain the absorption edge by a Tauc plot. Further, the energy of the absorption edge was used as an energy gap to find that an energy gap of DPAO11 was 2.99 eV. Accordingly, it was found that the oxadiazole derivative DPAO11 of the present invention has high excitation energy. In addition, when the ionizing potential of DPAO11 in a thin film state was measured with a photoelectron spectrometer (AC-2, by RIKEN KEIKI CO., LTD.) in the air, the ionizing potential was 5.41 eV. As a result, it was found that the HOMO level was -5.41 eV. Further, when the LUMO level was calculated from the value of the energy gap and the HOMO level obtained as described above, the LUMO level was -2.42 eV. Further, the glass transition point was measured with a differential scanning calorimeter (DSC Pyris 1, by PerkinElmer Inc.). After a sample was heated to 280 C. at 40 C./min, it was cooled to room temperature at 40 C./min. After that, the temperature was raised to 280 C. at 10 C./min, the sample was cooled to room temperature at 40 C./min, and the glass transition point was measured. As a result, it was found that the glass transition point (Tg) of DPAO11 was 72 C. Subsequently, an oxidation property and a reduction property of DPAO11 were examined by cyclic voltammetry (CV). The measurement device, and the solution and the concentration for the CV measurement were the same as those of Synthesis Example 1. The oxidation property was measured by first scanning potential of the working electrode with respect to the reference electrode from -0.35 to 0.60 V and then continuously scanning the potential from 0.60 to -0.35 V. In addition, the reduction property was measured by first scanning potential of the working electrode with respect to t...

Reference： [1]Patent: US2007/149784,2007,A1 .Location in patent: Page/Page column 71-72

35
[ 591-50-4 ]
[ 74-31-7 ]
copper [ No CAS ]
[ 19606-98-5 ]

Yield	Reaction Conditions	Operation in experiment
29%	With potassium carbonate; In ethanol; hexane; toluene;	Example 3 (Synthesis of N,N,N'-triphenyl-1,4-phenylenediamine (10)) 100.0 g of N,N'-diphenyl-1,4-phenylenediamine, 78.4 g of iodobenzene, 265.5 g of potassium carbonate and 77 g of copper powder and mesitylene as a reaction solvent were placed in a 2 L capacity four necked glass flask, and the reaction was carried out at a temperature of 160C for 10 hours under a nitrogen atmosphere. After the reaction, the resultant reaction mixture was extracted with toluene and the toluene solution was concentrated. Ethanol was added to the resulting concentrate and the resulting mixture was stirred for a little while, followed by removing resulting precipitates by filtration. The filtrate was concentrated to provide viscose liquid, to which a mixed solvent of toluene/hexane was added, and the resulting mixture was subjected to silica gel chromatography. The obtained fractions containing the reaction product were concentrated to provide viscose liquid, to which hexane was added. After the mixture was stirred for a little while, the resulting precipitates were collected by filtration, and dried, to provide 37.5 g of the desired N,N,N'-triphenyl-1,4-phenylenediamine as white solid. The yield was 29%.

Reference： [1]Patent: EP1829855,2007,A1

36
[ 13716-12-6 ]
[ 523-27-3 ]
[ 19606-98-5 ]
9,10-bis[N-(4-diphenylaminophenyl)-N-phenylamino]anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	palladium diacetate; In o-xylene; water;	Example 5 (Synthesis of 9,10-bis[N-(4-diphenylaminophenyl)-N-phenylamino]-anthracene) A hexane solution of 40.0 g of N,N,N'-triphenyl-1,4-phenylenediamine, 15.9 g of 9,10-dibromoanthracene, 21.9 g of sodium t-butoxide, 0.10 mg of palladium acetate and 0.38 g of tri-t-butylphosphine were dissolved in 300 mL of o-xylene. The reaction was carried out at a temperature of 70C for 8 hours under a nitrogen atmosphere. After the reaction, water was added to the resulting reaction mixture and the resulting red precipitates were collected by filtration. The precipitates were dissolved in hot toluene, and the resulting solution was filtered while hot to remove impurities therefrom, followed by cooling, to provide 24.7 g of 9,10-bis[N-(4-diphenylaminophenyl)-N-phenylamino]anthracene as red solid. The yield was 24%.

Reference： [1]Patent: EP1829855,2007,A1

37
palladium t-butylphosphinebromide [ No CAS ]
[ 83-53-4 ]
[ 19606-98-5 ]
magnesium sulfide [ No CAS ]
1,4-bis[N-(4-diphenylaminophenyl)-N-phenylamino] naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	In o-xylene; water; toluene;	(Synthesis of 1,4-bis[N-(4-diphenylaminophenyl)- N-phenylamino]-naphthalene (8)) 26.5 g of N,N,N'-triphenyl-1,4-phenylenediamine, 9.0 g of 1,4-dibromonaphthalene, 6.0g of sodium t-butoxide and 0.008 g of palladium t-butylphosphinebromide dimmer were dissolved in 200 mL of o-xylene. The reaction was carried out at a temperature of 70C for 5 hours under a nitrogen atmosphere. After the reaction, the resulting reaction mixture was extracted with a mixture of water/toluene and the organic layer was dehydrated over anhydrous magnesium sulfide, followed by concentration. The resulting concentrate was fractionated by chromatography on a column of silica gel and the desired fractions were concentrated under reduced pressure to provide solid. The solid was recrystallized from toluene and was then subjected to sublimation purification, thereby providing 3.9 g of 1,4-bis[N-(4-diphenylamino-phenyl)-N-phenylamino]naphthalene (1) as yellow solid. The yield was 16%.

Reference： [1]Patent: EP1829855,2007,A1

38
[ 19606-98-5 ]
[ 171408-76-7 ]
DPASF [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium t-butanolate;bis(dibenzylideneacetone)-palladium(0); In hexane; toluene; at 80℃; for 11h;	2.5 g (6.3 mmol) of 2-bromo-spiro-9,9'-bifluorene, 2.2 g (6.5 mmol) of DPA, 37.6 mg (0.063 mmol) of bis(dibenzyhdeneacetone)palladium(0), and 2.1 g (21 mmol) of t-butoxysodium were placed in a 100 mL three-necked flask. Nitrogen substitution was carried out, 50 mL of toluene was added, and the mixture was degassed at reduced pressure. 0.1 mL of tri(t-butyl)phosphine (10wt% hexane solution) was added, and the mixture was stirred for 11 hours at 800C. After the re'action, filtration was done through Celite. The filtrate was washed 3 times with water and once with a saturated saline solution, and dried with magnesium sulfate. The reaction mixture was naturally filtered, the filtrate was concentrated, and an oily product was obtained. This oily product was purified by silica gel column chromatography (hexanertoluene = 7:3), and after recrystallizing from dichloromethane and hexane, the target product of a white powdered solid was obtained, weighing 3.8 g in a yield of 91%. It was confirmed that this white powdered solid was DPASF by a nuclear magnetic resonance method (NMR). [0288]1H NMR of the compound obtained is shown below. Further, a 1H NMR chart is shown in FIG 10.1H NMR (300 MHz, DMSO-d6); δ = 7.95 (d, J=7 80 Hz, 2H), 7.90 (d, J=7.80 Hz, 2H), 7.40-7.77 (m, 26H), 6.67 (d, J=7.20 Hz, 2H), 6.55 (d, J=7.20 Hz, IH), 6.16 (d, J=2.33 Hz, IH) EPO <DP n="86"/>[0289]A synthesis scheme (c-1) of DPASF is shown below.

Reference： [1]Patent: WO2007/43354,2007,A1 .Location in patent: Page/Page column 84-85

39
[ 19606-98-5 ]
[ 171408-84-7 ]
DPA₂SF [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With tri-tert-butyl phosphine; sodium t-butanolate;bis(dibenzylideneacetone)-palladium(0); In hexane; toluene; at 80℃; for 6h;	5.0 g (10.6 mmol) of 2, 7-dibromo-spiro-9,9'-bifluorene, 7.4 g (21.0 mmol) of DPA, 63 mg (0.1 mmol) of bis(dibenzylideneacetone)palladium(0), and 3.6g (37 mmol) of t-butoxysodium were placed in a 300 mL three-necked flask, and nitrogen substitution was conducted. 100 mL of toluene was added to the mixture, and the mixture was degassed at reduced pressure. 0.05 mL of tri(t-butyl)phosphine (10 wtpercent hexane solution) was added, and the mixture was stirred for 6 hours at 8O0C. After the reaction, the mixture was filtered through Celite. The filtrate was washed 3 times with EPO <DP n="103"/>water and once with a saturated saline solution, then dried with magnesium sulfate. The reaction mixture was naturally filtered, and the filtrate was concentrated to obtain an oily product. This oily product was purified by silica gel column chromatography (hexane:ethyl acetate = 7:3), and recrystallized with chloroform and ethanol, giving 6.0 g of a pale yellow powdered solid in a yield of 57percent. It was confirmed that this pale yellow powdered solid was DPA2SF by a nuclear magnetic resonance method (NMR). [0363]1H NMR of the compound obtained is shown below. Also, a 1H NMR chart is shown in FIG. 27.1H NMR (300 MHz, DMSO-d6), delta=7.84 (d, J= 7.21 Hz, 2H), 7.77 (d, J= 7.80 Hz, 2H), 7.32-7 79 (m, 40H), 6.73 (d, J= 7.80 Hz, 2H), 6.16 (d, J= 2.10 Hz, 2H) [0364]A synthesis scheme (i-1) of DPA2SF is shown below. [0366]Sublimation purification was conducted on 2.0 g of the DPA2SF for 24 hours at a pressure of 6.7 Pa and a temperature of 3500C. 1.3 g was recovered, in a yield of 66percent.

Reference： [1]Patent: WO2007/43354,2007,A1 .Location in patent: Page/Page column 101-102

40
[ 1029634-23-8 ]
[ 19606-98-5 ]
[ 1029634-25-0 ]

Yield	Reaction Conditions	Operation in experiment
47%	With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In toluene; for 2h;Heating / reflux;	The compound of Formula b (3.0 g, 5.3 mmol) and4-(N-phenyl-N-phenylamino)phenyl-l-phenylamine (4.12 g, 12.3 mmol) were dissolved in 80 ml of toluene, and sodium-tertiary-butoxide (1.54 g, 16.0 mmol), bisdibenzylidene acetone palladium(O) (0.06 g, 0.11 mmol), and 50 wt% tri- tertiary-butylphosphine toluene solution (0.06 ml, 0.16 mmol) were added thereto. After reflux was conducted in a nitrogen atmosphere for 2 hours, distilled water was added to the reaction solution to complete the reaction. The organic layer was extracted, and a column separation process was conducted using a solvent of n-hexane and tetrahydrofuran (n-hexane/THF = 4/1), stirring was conducted using petroleum ether, and vacuum drying was conducted to produce the compound of Formula 2-1-1 (2.7 g, yield 47%).[134] MS: [M+H]+= 1076.
47%	With tri-tert-butyl phosphine; sodium t-butanolate;bis(dibenzylideneacetone)-palladium(0); In toluene; for 2h;Inert atmosphere; Reflux;	2) The compound of Formula b (3.0 g, 5.3 mmol) and 4-(N-phenyl-N-phenylamino)phenyl-1-phenylamine (4.12 g, 12.3 mmol) were dissolved in 80 ml of toluene, and sodium-tertiary-butoxide (1.54 g, 16.0 mmol), bis-dibenzylidene acetone palladium(0) (0.06 g, 0.11 mmol), and 50 wt % tri-tertiary-butylphosphine toluene solution (0.06 ml, 0.16 mmol) were added thereto. After reflux was conducted in a nitrogen atmosphere for 2 hours, distilled water was added to the reaction solution to complete the reaction. The organic layer was extracted, and a column separation process was conducted using a solvent of n-hexane and tetrahydrofuran (n-hexane/THF=4/1), stirring was conducted using petroleum ether, and vacuum drying was conducted to produce the compound of Formula 2-1-1 (2.7 g, yield 47%).MS: [M+H]+=1076.

Reference： [1]Patent: WO2008/66358,2008,A1 .Location in patent: Page/Page column 48
[2]Patent: US2010/65828,2010,A1 .Location in patent: Page/Page column 116

41
[ 19606-98-5 ]
[ 165550-62-9 ]
[ 937042-74-5 ]

Yield	Reaction Conditions	Operation in experiment
39%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; at 80℃; for 16h;	Step a):A mixture of 0.50 g (0.89 mmol) of N-(2,6-diisopropylphenyl)-9-bromoperylene-3,4-dicarboximide, 0.46 g (1.30 mmol) of <strong>[19606-98-5]N,N,N'-triphenyl-p-phenylenediamine</strong>, 20 mg (0.018 mmol) of tris(dibenzylideneacetone)dipalladium(0), 90 mg (0.045 mmol) of tris(tert-butyl)phosphine, 130 mg (1.3 mmol) of sodium tert-butoxide and 10 ml of dry toluene were heated to 80 C. under nitrogen and stirred at this temperature for 16 h.After the solvent had been distilled off, the crude product was subjected to column chromatography on silica gel with chloroform as the eluent.0.285 g of the amine-substituted perylene was obtained in the form of a violet solid, which corresponds to a yield of 39%.Analytical Data:UV-Vis (CH2Cl2): λmax=598 nmMS (FD): m/z (rel. int.)=815.3 (100%) [M+].

Reference： [1]Patent: US2008/269482,2008,A1 .Location in patent: Page/Page column 50

42
[ 4316-56-7 ]
[ 62-53-3 ]
[ 19606-98-5 ]

Yield	Reaction Conditions	Operation in experiment
77.6%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 130℃;	General procedure: bromobenzene (40.68 g, 259.09 mmol) was added to a round bottom flask and dissolved in toluene (1360 ml)aniline (26.54 g, 285.00 mmol),Pd2 (dba) 3 (7.12 g, 7.77 mmol),50% P (t-Bu) 3 (10.1 mL, 20.73 mmol) And NaOt-Bu (74.70 g, 777.28 mmol) were added,And stirred at 80 C. Upon completion of the reaction, extraction with CH2Cl2 and water, the organic layer was dried over MgSO4 and concentrated. Thereafter, the concentrate was passed through a silica gel column,And recrystallized to obtain 32.88 g (yield: 75%) of the product Sub2-1.
56%		Aniline (10 ml, 109.74 mmol) and the compound L prepared in Preparation Example 12 (30.7 g, 109.7 mmol) were dissolved in 300 ml of toluene. Then, bis(dibenzylidene-acetone)palladium (0) (Pd(dba) , 1.26 g, 2.20 mmol), 50 wt% of tri-? -butylphosphine (1.30 ml, 3.29 mmol) and sodium ?-butoxide (21.09 g, 219.5 mmol) were added thereto, and refluxed under nitrogen atmosphere for 2 hrs. Distilled water was added to the reaction solution to terminate the reaction. The organic layer was extracted, and separated by column chromatography using n-hexane/THF (10/1), stirred in pet. Ether, and dried under vacuum to obtain a compound N (15 g, yield 56%).[146] MS: [M+H]+ = 336.
47%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In o-xylene; at 130℃; for 15h;Inert atmosphere;	It is p-chlorotriphenylamine in the 300mL four mouth flask provided with the stirring device under a nitrogen atmosphere. 8.00 g (27.0mmol), Aniline 3.27 g (35.1mmol), tert-butoxysodium 3.12 g (32.5mmol), Palladium acetate 61 mg (0.27mmol), tritertbutylphosphine 218 mg (1.08mmol), o-xylene 100 mL was added and it stirred at 130 degreesC for 15 hours. After ending reaction, pure water 100 mL and toluene 100 mL was added andwashing liquid separation was carried out. It is pure water about the obtained organic layer.After carrying out washing liquid separation with 100 mL and then a saturated sodium chloridesolution, the obtained organic layer was concentrated in vacuum and the solvent was distilledoff. Silica gel column chromatography refines the obtained residue, and it is white powder. 4.30g was obtained (yield 47%, purity 96.9%). From the result of mass analysis, it checked thatthe obtained white powder was the target compound (G1).

Reference： [1]Patent: KR2019/37772,2019,A .Location in patent: Paragraph 0130; 0134-0136; 0143; 0144; 0147; 0148
[2]Patent: WO2008/133459,2008,A1 .Location in patent: Page/Page column 54
[3]Patent: JP5935283,2016,B2 .Location in patent: Paragraph 0142; 0143

43
[ 27973-29-1 ]
[ 19606-98-5 ]
[ 1193362-65-0 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 8472 - 8475

44
[ 19606-98-5 ]
[ 74-88-4 ]
[ 1287224-97-8 ]

Reference： [1]Journal of the Chinese Chemical Society,2009,vol. 56,p. 493 - 503

45
[ 19606-98-5 ]
[ 925674-50-6 ]
[ 1019779-54-4 ]

Yield	Reaction Conditions	Operation in experiment
59%	With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In hexane; xylene; at 110℃; for 7h;Inert atmosphere;	Embodiment 4In this embodiment, a synthetic method of N-{4-[(E)-4-(diphenylamino)styryl]phenyl}-N,N',N'-triphenyl-1,4-phenylenediamine represented by the following structure (hereinafter, abbreviated as “DPAPhAS”) in which A11 corresponds to the general formula (1-1) of the general formula (1) is shown. First, (E)-4-bromo-4'-(N,N-diphenyl)aminostilbene was synthesized in accordance with synthetic schemes (b-1) and (b-2) shown in Embodiment 2. Then, in a 50 mL three-neck flask, 490 mg (1.2 mmol) of (E)-4-bromo-4'-(N,N-diphenyl)aminostilbene; 400 mg (1.2 mmol) of N,N,N'-triphenyl-1,4-phenylenediamine (abbreviation: DPA); 55 mg (0.1 mmol) of bis(dibenzylideneacetone)palladium(0); and a suspension of 200 mg (2.0 mmol) of sodium tert-butoxide, 15 mL of dehydrated xylene, and 600 μL (0.3 mmol) of tri-tert-butylphosphine (10% hexane solution) were heated and stirred at 110 C. for 7 hours under a nitrogen atmosphere.After the completion of the reaction, approximately 200 mL of toluene was added to this suspension, and the mixture was subjected to suction filtration through Florisil, alumina, and celite. The obtained filtrate was washed with water and dried with magnesium sulfate. This suspension was filtered through Florisil, alumina, and celite, and the obtained filtrate was concentrated. This concentrate was subjected to silica gel column chromatography (a developing solvent was a mixed solution of toluene and hexane), and the target substance was obtained. The obtained target substance was recrystallized with an acetate:hexane mixed solvent.480 mg of N-{4-[(E)-4-(diphenylamino)styryl]phenyl}-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: DPAPhAS), a yellow powder which was the target substance, was obtained in a yield of 59%. Rf values in silica gel thin layer chromatography (TLC) (in the developing solvent, hexane:ethyl acetate=10:1) were as follows: the target substance was 0.45, (E)-4-bromo-4'-(N,N-diphenyl)aminostilbene was 0.55, and DPA was 0.34.1H NMR data is shown below. FIGS. 29A and 29B are each a 1H NMR chart, and FIG. 29B is an enlarged chart of the 6 ppm to 9 ppm range in FIG. 29A.1H NMR (CDCl3, 300 MHz): δ=6.93 (s, 2H), 6.98-7.27 (m, 33H), 7.35 (d, J=8.4 Hz, 4H)

Reference： [1]Patent: US7732619,2010,B2 .Location in patent: Page/Page column 91-92

46
[ 1123921-68-5 ]
[ 19606-98-5 ]
[ 1123921-70-9 ]

Yield	Reaction Conditions	Operation in experiment
66%	With tri-tert-butyl phosphine; sodium t-butanolate;bis(dibenzylideneacetone)-palladium(0); In hexane; toluene; at 80℃; for 5h;Inert atmosphere;	0.84 g (1.7 mmol) of 2-(4-bromophenyl)-9,10-diphenylanthracene synthesized in Step 2 of Example 1, 0.30 g (3.1 mmol) of sodium tert-butoxide, 0.53 g (1.60 mmol) of N,N',N'-triphenyl-1,4-phenylenediamine, and 0.03 g (0.06 mmol) of bis(dibenzylideneacetone)palladium(0) were put into a 50 mL three-neck flask and the atmosphere in the flask was substituted by nitrogen. 10 mL of toluene and 0.02 mL of tri(tert-butyl)phosphine 10 wt % hexane solution were added to this mixture. This mixture was stirred while being heated at 80 C. for five hours to be reacted. After reaction, toluene was added into the reacted mixture, and this suspension was subjected to suction filtration through Celite (manufactured by Celite Co., Ltd.), Florisil (manufactured by Floridin Company), and alumina so that a filtrate was obtained. The obtained filtrate was washed with water and saturated brine, and magnesium sulfate was added to an organic layer to be dried. This mixture was subjected to suction filtration to remove magnesium sulfate, so that a filtrate was obtained. A solid substance obtained by concentrating the obtained filtrate was purified by silica gel column chromatography (a developing solvent was a mixed solvent of toluene:hexane=1:10 and then a developing solvent was a mixed solvent of toluene: hexane=1:3). The obtained fraction was concentrated to obtain a solid substance. The solid substance was recrystallized with a mixture solvent of dichloromethane and methanol, so that 0.84 g of a light yellow powdered solid substance was obtained in 66% yield. By a nuclear magnetic resonance measurement (NMR), this compound was proved to be 2-{4-[N-(4-diphenylaminophenyl)-N-phenylamino]phenyl}-9,10-diphenylanthracene (abbreviation: 2DPAPPA).

Reference： [1]Patent: US8288012,2012,B2 .Location in patent: Page/Page column 154-155

47
[ 19606-98-5 ]
[ 525602-17-9 ]
C₇₈H₆₀N₆ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 8627 - 8633,7

48
[ 108-86-1 ]
[ 74-31-7 ]
[ 19606-98-5 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 8627 - 8633,7

49
[ 34658-66-7 ]
[ 19606-98-5 ]
[ 1246635-31-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In hexane; toluene; at 120℃; for 5h;Inert atmosphere;	Example 4In Example 4, an example of a synthesis method of N-[4-(imidazo[1,2-a]pyridin-2-yl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: DPAPIM) which is represented by a structural formula (100) will be described. A synthesis scheme is shown in the following (E4-1). In a 100 mL three-necked flask were placed 1.6 g (5.9 mmol) of <strong>[34658-66-7]2-(4-bromophenyl)imidazo[1,2-a]pyridine</strong>, 1.4 g (15 mmol) of sodium tert-butoxide, 2.0 g (5.9 mmol) of N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: DPA), and 0.20 g (0.35 mmol) of bis(dibenzylideneacetone)palladium(0), and the atmosphere in the flask was replaced with nitrogen.To this mixture were added 30 mL of toluene and 0.20 mL of a 10% hexane solution of tri(tert-butyl)phosphine. This mixture was stirred under a nitrogen stream at 120 C. for 5 hours. After the stirring, toluene was added to this mixture, and this suspension was subjected to suction filtration through Celite to give a filtrate. The obtained filtrate was washed with water and a saturated saline solution in this order, and then the organic layer was dried with magnesium sulfate. After the drying, this mixture was subjected to suction filtration to give a filtrate. The obtained filtrate was concentrated to give a compound. The obtained compound was purified by silica gel column chromatography. The silica gel column chromatography was performed by, first, using a mixed solvent of toluene and hexane (toluene:hexane=1:2) as a developing solvent, and then using toluene as another developing solvent. The obtained fraction was concentrated to give a solid. This solid was recrystallized with a mixed solvent of chloroform and hexane to give 2.5 g of a white powdered solid in a yield of 80%.In addition, 2.5 g of the obtained solid was sublimated and purified by train sublimation. The sublimation purification was performed under a reduced pressure of 7.0 Pa, with a flow rate of argon at 3.0 mL/min, at 281 C., and for 22 hours. After the sublimation purification, 2.0 g of a target substance was obtained in a yield of 80%.By a nuclear magnetic resonance (NMR) method, this compound was confirmed to be N-[4-(imidazo[1,2-a]pyridin-2-yl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: DPAPIM), which was a target substance.1H NMR data of the obtained compound is shown below: 1H NMR (CDCl3, 300 MHz): delta=6.75 (td, J1=6.4 Hz, J2=0.98 Hz, 1H), 6.95-7.29 (m, 22H), 7.60 (d, J=9.8 Hz, 1H), 7.77 (s, 1H), 7.83 (d, J=8.8 Hz, 2H), 8.08 (d, J=6.8 Hz, 1H)

Reference： [1]Patent: US8329917,2012,B2 .Location in patent: Page/Page column 104-106

50
[ 81-86-7 ]
[ 19606-98-5 ]
4-(N-phenyl-N-(4-(N',N''-diphenyl)amino)phenyl)amino-1,8-naphthalene anhydride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; at 95℃; for 3h;Inert atmosphere;	General procedure: To a three-necked flask, 4-bromo-1,8-naphthalic anhydride(276 mg, 1 mmol), diphenylamine (254 mg, 1.5 mmol),[Pd(dppf)Cl2] (3.65 mg, 0.0050 mmol) and cesium carbonate(488 mg, 1.5 mmol) were added. The flask was purged with nitrogengas for several times and then 1,4-diethylene dioxide (3 ml)was added via a syringe [29]. The mixture was heated to 95 C underthe protection of nitrogen flow and kept at this temperature forabout 3 h. After cooled to room temperature, a mixture of water(3 ml) and ethyl acetate (20 ml) was added to the flask, the organiclayer was then separated from the aqueous layer in a separationfunnel and washed successively with water and brine solution.The organic layer was dried over anhydrous magnesium sulfatefor overnight. After filtration, the solvents were removed under reducedpressure. The residue was purified by column chromatographyon silica gel with chloroform/petroleum (v/v = 2/1) as eluent.Compound 2 was collected as orange powder (315.4 mg, 85%). red solid(266.5 mg, 50%). Mp > 300 C; 1H NMR (300 MHz, CDCl3, 25C,TMS): 8.56-8.47 (m, 2H), 8.27 (d, 1H), 7.56-7.50 (t, 1H), 7.40 (d,1H), 7.31-7.24 (m, 7H), 7.11-6.91 (d, 12H). MS (MALDI-TOF): m/z, calculated for C36H24O3N2: 532.18, found: 533.19 [M + H]+. Elementalanalysis (%) calculated for C36H24O3N2: C 81.17, H 4.51, N5.26; found: C 80.63, H 4.72, N 4.72. IR (KBr, cm1) 1690 (masCO), 1662 (ms CO).

Reference： [1]Journal of Molecular Structure,2014,vol. 1056-1057,p. 339 - 346

51
[ 106-37-6 ]
[ 19606-98-5 ]
N1-(4-bromophenyl)-N1,N4,N4-triphenyl-1,4-benzenediamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In toluene; at 95℃; for 12h;Inert atmosphere;	Catalyst B (in 10 mL of toluene) was added to the solution of V (5.5 g, 15 mmol), 1,4-dibromobenzene (10.61 g, 45 mmol) and sodium tert-butoxide (2.1 g, 22 mmol) in toluene (50 mL) and the mixture was stirred at 95C for 12 h under an argon atmosphere. The reaction was stopped by opening the reaction to the air and the insoluble material was removed by filtration. The product was isolated by column chromatography. First, 1,4,-dibromobenzene was eluted with cyclohexane followed by elution of the product with toluene.

Reference： [1]Chemical Papers,2016,vol. 70,p. 1238 - 1252

52
[ 19606-98-5 ]
N¹-{4-[(diphenylmethylene)amino]phenyl}-N¹,N⁴,N⁴-triphenyl-1,4-benzenediamine [ No CAS ]

Reference： [1]Chemical Papers,2016,vol. 70,p. 1238 - 1252

53
[ 19606-98-5 ]
N1-(4-aminophenyl)-N1,N4,N4-triphenyl-1,4-benzenediamine [ No CAS ]

Reference： [1]Chemical Papers,2016,vol. 70,p. 1238 - 1252

54
[ 19606-98-5 ]
N-{4-[4-(diphenylamino)-N-phenylanilino]phenyl}-2-methylacrylamide [ No CAS ]

Reference： [1]Chemical Papers,2016,vol. 70,p. 1238 - 1252

55
[ 36809-26-4 ]
[ 19606-98-5 ]

Reference： [1]Patent: JP5648101,2015,B2

56
[ 887951-17-9 ]
[ 19606-98-5 ]
9,10-bis{4-[N-(4-diphenylamino)phenyl-N-phenyl]aminophenyl}-2-tert-butyl anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In hexane; toluene; at 80℃; for 8h;Inert atmosphere;	In 200ml three-necked flask, 9,10-bis (4-bromo-phenyl) -2-tert- butyl anthracene 2.00g (0.0037mol), N- (4- diphenyl-amino) phenyl aniline 2.61g (0.0078mol) , bis dibenzylideneacetone palladium 428 mg (0.77mmol), placed tert- butoxide sodium 2.00 g (0.021 mol), after the inside of the system under a nitrogen flow, dehydrated toluene 20ml and tri -tert- butylphosphine 10 % hexane solution 4.0 ml was added, and the mixture was stirred for 8 hours at 80 . After completion of the reaction, cooled the reaction solution to room temperature, twice washed reaction solution with water, the aqueous layer was extracted twice with chloroform, washed with saturated brine and combined with the organic layers were dried over magnesium sulfate. Then concentrated natural filtration, the resulting brown oily matter was purified by silica gel chromatography (hexane: ethyl acetate = 9: 1) after purification by, dichloromethane, 1.14 g yield a yellow powdery solid was recrystallized with hexane It was obtained in 29% (synthesis scheme (d-1)). By nuclear magnetic resonance spectroscopy (1H-NMR), this yellow powdery solid 9,10-bis {4- [N- (4- diphenylamino) phenyl -N- phenyl] amino phenyl} -2-tert- butyl anthracene (abbreviation: DPABPA) was confirmed to be.

Reference： [1]Patent: JP5648101,2015,B2 .Location in patent: Paragraph 0122-0123; 0125-0126

57
[ 328-70-1 ]
[ 19606-98-5 ]
C₃₂H₂₂F₆N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; for 0.25h;Inert atmosphere;	N1,N1,N4-triphenylbenzene-1,4-diamine (1.0 g, 3.0 mmol) and 1-bromo-3,5-bis(trifluoromethyl)benzene (1.15 g, 3.9mmol) to 70 mL of xylene were mixed in dry. The solution was bubbling with nitrogen for 15 minutes. Then, Pd2(dba)3 (0.29 g, 0.32 mmol), 2-dicyclohexylphosphino-2 ',6'-di-methoxy-biphenyl fertilization (0.58 g, 1.20 mmol) and tBuONa (0.44 g, 4.50 mmol) It was added to the solution. The mixture was refluxed overnight under a nitrogen atmosphere. After cooled, filtered through celite / silica pad to the reaction mixture, the filtrate was concentrated. Then, the residue as the eluant DCM: hexane (1: 4, v / v) and purified by column chromatography using compound 743 was collected in .1.3 g (80%).

Reference： [1]Patent: KR2015/56046,2015,A .Location in patent: Paragraph 0242; 0243; 0244

58
[ 19606-98-5 ]
C₂₃H₁₅BrN₂ [ No CAS ]
C₄₇H₃₄N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%		In a two-neck 250 ml flask, 9 (1.2 g, 3.1 mmol), N, N, N-triphenylbenzene-1,4-Diamine, 1 g, 3 mmol), NaOTBu (0.86 g, 9 mmol) was added to toluene (100 ml), stirred under nitrogen, and the reaction temperature was raised to 80 CAnd the reaction is allowed to proceed for 1 hour. To this was added Pd (dba) 2 (0.05 g, 0.09 mmol) and (tert-Bu) 3P (0.03 g, 0.12 mmol)The reaction is carried out at 80 for a period of time. The reaction solution is filtered to remove the salt. The filtrate was distilled to remove tolueneThe concentrate was separated into columns and the yield of DPAA-P-BPaC3 was 1.2 g (yield: 65%).

Reference： [1]Patent: KR2015/9205,2015,A .Location in patent: Paragraph 0142; 0143; 0144; 0148; 0149; 0151

59
[ 19606-98-5 ]
C₂₃H₁₇Cl [ No CAS ]
C₄₇H₃₆N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In o-xylene; at 130℃; for 10h;Inert atmosphere;	A stirring device under a nitrogen atmosphere in the 100mL four mouth flask which it had A0.720 g (2.13mmol) compound (G1), A 0.700 g (2.13mmol) compound (C4) and tertbutoxysodium 0.250 g (2.60mmol), Palladium acetate 5 mg (0.02mmol), tritertbutylphosphine 18 mg (0.09mmol), o-xylene 10 mL was added and it stirred at 130 degrees Cfor 10 hours. After ending reaction, pure water 30 mL and toluene 15 mL was added andwashing liquid separation was carried out. After carrying out washing liquid separation of theobtained organic layer with 30 mL of pure water, and then a saturated sodium chloridesolution, the obtained organic layer was concentrated in vacuum and the solvent was distilledoff. Silica gel column chromatography refines the obtained residue, and it is white powder. 0.55g was obtained (yield 41%, purity 99.7%). From the result of mass analysis, it checked thatthe obtained white powder was the target compound (A67).

Reference： [1]Patent: JP5935283,2016,B2 .Location in patent: Paragraph 0142; 0144

60
[ 19606-98-5 ]
dibenzo[f,h]quinoxalin-2-yl trifluoromethanesulfonate [ No CAS ]
C₄₀H₂₈N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; for 48h;Inert atmosphere; Reflux;	N’,N’,N4-triphenylbenzene-1,4-diamine (0.089 g, 0.3 mmol) and dibenzo[f,h]quinoxalin-2-yl trifluoromethanesulfonate (0.1 g, 0.3 mmol) were mixed in 10 mL of xylene. The solution was bubbled with nitrogen for 15 min. Pd2(dba)3 (0.012 g, 0.01 mmol), 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl (0.011 g, 0.03 mmol) and sodium t-butoxide (0.025 g, 0.3 mmol) were added. The mixture was refluxed for 2 days under nitrogen. After cooling, the reaction mixture was filtered and the solvent was evaporated. The residue was then purified by column chromatography using gradient from hexane to toluene:hexane (1:1, v/v) as eluent, yielding 0.86 g (58%) of Compound 4-H.

Reference： [1]Patent: US9537106,2017,B2 .Location in patent: Page/Page column 343; 344

61
9-(3,5-dibromophenyl)-9H-carbazole [ No CAS ]
[ 19606-98-5 ]
C₆₆H₄₉N₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In o-xylene; at 130℃; for 6h;Inert atmosphere;	An 100 mE 3-neck round bottom flask was charged withnitrogen, and then a compound A which is 9-(3,5-dibro-mophenyl)-9H-carbazole (24.7 mmol, 9.9 g), a compound E which is (4-anilinophenyl)diphenylamine (54.3 mmol, 18.3 g), palladium acetate (Pd(OAc)2 2.5 mmol, 0.6 g), sodium tert-butoxide (54.3 mmol, 5.2 g), 50 mE of o-xylene, andtri-tert-butylphosphine (5.0 mmol, 1.2 mE) were added thereto, and the resulting mixture was heated at 130 C. for 6 hours. The solution of the mixture was cooled to room temperature, stirred in 750 mE of methanol for 20 minutes, and filtered, thereby obtaining 15.9 g of a white solid,Compound 3 (yield: 70%).MAEDI-TOF: mlz=91 1.2232 (C55H49N5=9 12.13)1H-NMR (CDC13, 500 MHz) ö: 8.19 (d, J=7.68 Hz, 2H),7.41 (d, J=8.21 Hz, 2H), 7.36 (t, J=7.25 Hz, 2H), 7.31 (t,J=8.16 Hz, 4H), 7.26 (t, J=7.73 Hz, 1OH), 7.20 (d, J=7.72 Hz, 4H), 7.14 (d, J=8.80 Hz, 4H), 6.94-7.06 (m, 18H), 6.62 (s, 1H), 6.50 (d, J=1.85 Hz, 2H)

Reference： [1]Patent: US9680107,2017,B2 .Location in patent: Page/Page column 20

62
[ 19606-98-5 ]
9-(3,5-dibromophenyl)-3,6-diphenyl-9H-carbazole [ No CAS ]
C₇₈H₅₇N₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10 g	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In o-xylene; at 130℃; for 4h;Inert atmosphere;	A 250 mE 3-neck round bottom flask was charged with nitrogen, and then a compound B which is 9-(3,5-dibro- mophenyl)-3,6-diphenyl-9H-carbazole (9.1 mmol, 5.0 g), a compound L which is (4-anilinophenyl)diphenylamine (20.0mmol, 6.7 g), palladium acetate (Pd(OAc)2 0.9 mmol, 0.2 g), sodium tert-butoxide (20.0 mmol, 1.9 g), 100 mE of o-xylene, and tri-tert-butylphosphine (1.8 mmol, 0.4 mE) were added thereto, and the resulting mixture was heated at 130 C. for 4 hours. The solution of the mixture was cooled to room temperature, and 100 mE of tetrahydrofuran wasadded thereto. The mixture solution was stirred in 800 mE of methanol for 25 minutes, and filtered, thereby obtaining 10.0 g of a white solid, Compound 8 (yield: 103%).MAEDI-TOF: mlz=1063.61 52 (C78H57N5=1 064.32)1H-NMR (DMSO, 500 MHz) ö: 8.68 (s, 2H), 7.9 (d, J=7.5 Hz, 4H), 7.70 (d, J=8 Hz, 2H), 7.51 (t, J=8 Hz, 6H),7.38-7.34 (m, 6H), 7.22 (t, J=7 Hz, 12H), 7.17 (d, J=8 Hz,4H), 7.06 (t, J=6 Hz, 2H), 6.99-6.95 (m, 16H), 6.64 (s, 1H),6.58 (s, 2H)

Reference： [1]Patent: US9680107,2017,B2 .Location in patent: Page/Page column 25; 26

63
[ 19606-98-5 ]
5-(3,5-dibromophenyl)-5H-benzo[b]phosphindole [ No CAS ]
C₆₆H₄₉N₄P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In o-xylene; at 130℃; for 5h;Inert atmosphere;	An 100 mE 3-neck round bottom flask was charged withnitrogen, and then a compound F which is 5-(3,5-dibro-mophenyl)-5H-pentaphenylphosphole (24.6 mmol, 10.3 g), a compound E which is (4-anilinophenyl)diphenylamine (54.1 mmol, 18.2 g), palladium acetate (Pd(OAc)2) (2.5 mmol, 0.6 g), sodium tert-butoxide (54.1 mmol, 5.2 g), 65mE of o-xylene, and tri-tert-butylphosphine (4.9 mmol, 1.2 mE) were added thereto, and heated at 130 C. for 5 hours. The resulting solution was cooled to room temperature, stirred in 325 mE of methanol for 40 minutes, and filtered, thereby obtaining 14.2 g of a white solid, Compound 16 (yield: 62%).MALDI-TOF: m/z=927.3232 (C55H49N4P=928.37)

Reference： [1]Patent: US9680107,2017,B2 .Location in patent: Page/Page column 34; 35

64
[ 19606-98-5 ]
[ 436-59-9 ]
N₁-(dimesitylboryl)-N₁,N₄,N₄-triphenylbenzene-1,4-diamine [ No CAS ]

Reference： [1]Organometallics,2017,vol. 36,p. 2692 - 2701

65
[ 19606-98-5 ]
[ 105946-82-5 ]
C₃₆H₂₇BrN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With caesium carbonate; triphenylphosphine; sodium t-butanolate; In toluene; at 80℃; for 8h;Inert atmosphere;	Under argon, will be 10.09 g (30 mmol) intermediate A - 1, 10.77 g (30 mmol) 4 - iodo -4 ' - bromo biphenyl, 5.77 g (60 mmol) of sodium tert-butanol dissolved in 300 ml dehydration in toluene, added under mixing 0.14 g (0.6 mmol) of palladium acetate, 0.12 g (0.6 mmol) triphenylphosphine, in the 80 C lower reaction 8 hours. After cooling, the diatomite/silica gel funnel filter, the filtrate by reduced pressure distillation to remove the organic solvent, the obtained residue in toluene in the re-crystallization, drying, can get 14.47 g (25.5 mmol) intermediate C - 1, and the yield is 85%.

Reference： [1]Patent: CN108863918,2018,A .Location in patent: Paragraph 0081; 0086; 0087; 0088

66
[ 19606-98-5 ]
4,4'-(2-bromo-9H-fluorene-9,9-diyl)diphenol [ No CAS ]
C₄₉H₃₆N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		4,4'-(2-bromo-9H-fluorene-9,9-diyl)diphenol (3.00 g, 6.99 mmol),Triphenylbenzene-1,4-diamine(2.59 g, 7.68 mmol)And NaOtBu (3.36 g, 34.9 mmol) were added to degassed tolueneAnd tetrahydrofuran were dissolved in 200 mL and 50 mL, respectively. The temperature was raised to 60 DEG C and stirred for 30 minutes,Bis(tri-tert-butylphosphine) palladium (0.18 g, 0.35 mmol) was dissolved in tetrahydrofuran and reacted for about 18 hours.The reaction mixture was cooled to room temperature, the solvent was removed, and the organic layer was extracted several times with CH2Cl2 / H2O. Dried over MgSO4, adsorbed on palladium and filtered through celite and silica, respectively. The reaction solution was concentrated and flash column to synthesize intermediate 2-1.

Reference： [1]Patent: KR2019/5654,2019,A .Location in patent: Paragraph 0242-0244

67
[ 108-86-1 ]
[ 19606-98-5 ]

Reference： [1]Patent: KR2019/37772,2019,A

68
[ 62-53-3 ]
[ 19606-98-5 ]

Reference： [1]Patent: KR2019/37772,2019,A

69
[ 19606-98-5 ]
[ 93-91-4 ]
(5-(diphenylamino)-2-methyl-1-phenyl-1H-indol-3-yl)(phenyl)methanone [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 6736 - 6740

70
[ 19606-98-5 ]
C₃₄H₂₈N₂O [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 6736 - 6740

71
[ 19606-98-5 ]
C₃₄H₂₈N₂ [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 6736 - 6740

72
[ 19606-98-5 ]
C₂₀H₁₁ClS [ No CAS ]
C₄₄H₃₀N₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In o-xylene; at 140℃; for 4h;Inert atmosphere;	Under a nitrogen stream,In a 50 mL three-necked flask, compound (7) 2.0 g (6.2 mmol), compound represented by Amine 1 2.1 g (6.2 mmol), sodium tert-butoxide 0.84 g (8.7 mmol), and o -Xylene 20 mL was added. Palladium acetate (42 mg, 0.18 mmol) and tri (tert-butyl) phosphine (132 mg, 0.65 mmol) were added to the resulting slurry reaction solution, and the mixture was stirred at 140 C. for 4 hours. After cooling to room temperature, 15 mL of pure water was added and stirred. The product precipitated in the organic layer was collected by filtration and washed with water and ethanol. The resulting brown powder was recrystallized from o-xylene to give compound (C1)Was isolated in an amount of 3.5 g (5.6 mmol) (89% yield).

Reference： [1]Patent: JP2020/29416,2020,A .Location in patent: Paragraph 0117-0121

73
[ 603-76-9 ]
[ 19606-98-5 ]
6-methyl-N,N,5-triphenyl-5,6-dihydroindolo[2,3-b]indol-2-amine [ No CAS ]

Reference： [1]Chemical Communications,2020,vol. 56,p. 2807 - 2810

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CAS No. :	19606-98-5	MDL No. :	MFCD27939629
Formula :	C₂₄H₂₀N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OCQFHFNWMCLWKC-UHFFFAOYSA-N
M.W :	336.43	Pubchem ID :	161288
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
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P103	Read label before use
Prevention
Code	Phrase
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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:
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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. 19606-98-5 ] {[proInfo.proName]}

Quality Control of [ 19606-98-5 ]

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[ 19606-98-5 ] Synthesis Path-Downstream 1~73

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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