Conditions | Yield |
---|---|
With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 20℃; for 1h; | 99% |
With palladium diacetate; sodium t-butanolate; ruphos In neat (no solvent) at 110℃; for 24h; Catalytic behavior; Reagent/catalyst; Time; Buchwald-Hartwig Coupling; Inert atmosphere; Green chemistry; | 99% |
With palladium diacetate; sodium t-butanolate; ruphos In neat (no solvent) at 110℃; for 12h; Reagent/catalyst; Buchwald-Hartwig Coupling; Inert atmosphere; Green chemistry; | 99% |
Conditions | Yield |
---|---|
With (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl; sodium t-butanolate In neat (no solvent) at 110℃; for 12h; Reagent/catalyst; Buchwald-Hartwig Coupling; Inert atmosphere; Green chemistry; | 99% |
With potassium tert-butylate In toluene at 135℃; for 36h; | 78% |
With copper chromium oxide; potassium hydroxide In toluene for 18h; Ullmann Condensation; Inert atmosphere; Reflux; Green chemistry; | 43% |
With bis-triphenylphosphine-palladium(II) chloride; (E)-2-(((2,5-bis(trifluoromethyl)phenyl)imino)methyl)phenol; sodium t-butanolate In o-xylene at 145℃; for 12h; Schlenk technique; Inert atmosphere; |
Conditions | Yield |
---|---|
With palladium diacetate; sodium t-butanolate; ruphos In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Green chemistry; | 99% |
With C30H41ClPPd; sodium t-butanolate In toluene at 100℃; for 2h; Buchwald-Hartwig Coupling; Inert atmosphere; | 99% |
With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 100℃; for 21h; | 98% |
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
aniline
N,N-diphenylaminobenzene
Conditions | Yield |
---|---|
With cesium fluoride In acetonitrile at 25℃; for 72h; | 98% |
With cesium fluoride In acetonitrile at 20℃; for 72h; | 98% |
Conditions | Yield |
---|---|
With potassium tert-butylate; 1,2-bis(2,6-diisopropylphenylimino)ethane; copper(l) iodide In toluene at 120℃; for 48h; | 97% |
With potassium tert-butylate In toluene at 120℃; for 12h; Ullmann coupling; Inert atmosphere; | 95% |
With copper chromium oxide; potassium hydroxide In toluene for 6h; Catalytic behavior; Reagent/catalyst; Solvent; Ullmann Condensation; Inert atmosphere; Reflux; Green chemistry; | 95% |
Conditions | Yield |
---|---|
With cesium fluoride; bis(dibenzylideneacetone)-palladium(0); XPhos at 100℃; for 1h; Inert atmosphere; | 97% |
With cesium fluoride; bis(dibenzylideneacetone)-palladium(0); XPhos at 100℃; for 1h; Time; Inert atmosphere; | 97% |
4-(diphenylamino)phenyl boronic acid
N,N-diphenylaminobenzene
Conditions | Yield |
---|---|
With silver nitrate; triethylamine In ethanol; water at 80℃; for 0.166667h; Solvent; Reagent/catalyst; | 97% |
With copper(ll) sulfate pentahydrate; oxygen; diisopropylamine In ethanol; water at 80℃; for 1.5h; Catalytic behavior; Reagent/catalyst; Green chemistry; | 96% |
Conditions | Yield |
---|---|
With bis(triphenylphosphine)nickel(II) chloride; ethylmagnesium bromide; triphenylphosphine In tetrahydrofuran at 80℃; for 3h; | 96% |
With [Pd{C6H4(CH2N(CH2Ph)2)}(μ-Br)]2; potassium hydroxide In dimethyl sulfoxide at 120℃; for 0.666667h; | 96% |
With potassium tert-butylate In toluene at 120℃; for 12h; | 95% |
2-((4-diphenylamino)phenyl)[1,3,2]dioxaborolane
N,N-diphenylaminobenzene
Conditions | Yield |
---|---|
With silver nitrate; triethylamine In ethanol; water at 80℃; for 0.233333h; | 96% |
Conditions | Yield |
---|---|
With N/O-doped porous carbon (on base of polypyrrole) supported nanopalladium In toluene at 160℃; for 36h; Reagent/catalyst; Inert atmosphere; Sealed tube; | 96% |
Conditions | Yield |
---|---|
With potassium tert-butylate; urea; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane at 100℃; for 46h; | 95% |
With ammonia; sodium; Petroleum ether | |
Multi-step reaction with 2 steps 1: sodium t-butanolate; (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl / neat (no solvent) / 12 h / 110 °C / Inert atmosphere; Green chemistry 2: sodium t-butanolate; (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl / neat (no solvent) / 12 h / 110 °C / Inert atmosphere; Green chemistry View Scheme |
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; potassium tert-butylate; copper(l) iodide In toluene at 115℃; for 3.5h; Product distribution; Further Variations:; Reagents; | A 95% B 2% |
With copper at 180℃; for 12h; | A 46% B 31% |
With copper(l) iodide; cesium fluoride In dimethyl sulfoxide at 130℃; for 24h; Ullmann Condensation; Inert atmosphere; Glovebox; | A 12% B 39 %Chromat. |
With potassium tert-butylate; copper(l) iodide; tributylphosphine In toluene at 110℃; for 3.5h; Product distribution; Further Variations:; Catalysts; high pressure; |
Conditions | Yield |
---|---|
With potassium tetrachloropalladate(II); L-arginine; potassium hydroxide In water at 80℃; for 2h; Reagent/catalyst; | 95% |
With potassium phosphate; copper(l) iodide; lithium amide In N,N-dimethyl-formamide at 130℃; for 24h; Inert atmosphere; chemoselective reaction; | 79% |
Multi-step reaction with 2 steps 1: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 24 h / Reflux 2: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 144 h / Reflux View Scheme | |
Multi-step reaction with 2 steps 1: Pd(tris[2-(diphenylphosphino)ethyl]phosphine tetrasulfide)(dibenzylideneacetone); caesium carbonate / isopropyl alcohol / 6 h / 80 °C 2: Pd(tris[2-(diphenylphosphino)ethyl]phosphine tetrasulfide)(dibenzylideneacetone); caesium carbonate / isopropyl alcohol / 24 h / 80 °C View Scheme | |
Multi-step reaction with 3 steps 1: ammonia; potassium carbonate / water; ethanol / 20 °C / UV-irradiation; Green chemistry 2: potassium carbonate / water; ethanol / 20 °C / UV-irradiation; Green chemistry 3: potassium carbonate / water; ethanol / 20 °C / UV-irradiation; Green chemistry View Scheme |
Conditions | Yield |
---|---|
With chloranil at -60℃; | 94% |
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon; sodium t-butanolate In 1,3,5-trimethyl-benzene for 24h; Inert atmosphere; Reflux; | 92% |
With dichloro{1,10-[dicyclohexylbenzyl]-3,3'-o-xylyldibenzimidazolidin-2,2'-diylidene}palladium (II); potassium tert-butylate In 1,2-dimethoxyethane at 80℃; for 15h; Buchwald-Hartwig amination; Inert atmosphere; | 92% |
With potassium hydroxide In water for 24h; Buchwald-Hartwig reaction; Reflux; Inert atmosphere; | 88% |
4-(diphenylamino)phenylboronic pinacol ester
N,N-diphenylaminobenzene
Conditions | Yield |
---|---|
With silver nitrate; triethylamine In ethanol; water at 80℃; for 0.916667h; | 92% |
With copper(ll) sulfate pentahydrate; oxygen; diisopropylamine In ethanol; water at 80℃; for 24h; Green chemistry; | 61% |
4-N,N-diphenylamino-1-bromobenzene
N,N-diphenylaminobenzene
Conditions | Yield |
---|---|
With 1,4-dioxane; 1,10-Phenanthroline; sodium hydride In mineral oil at 140℃; for 22h; Schlenk technique; Inert atmosphere; | 90% |
With tributyl-amine; tetrabutylammonium tetrafluoroborate In acetonitrile at 20℃; for 1.8h; Inert atmosphere; Electrolysis; | 80% |
With formic acid; C59H60N6O2Pt; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 4h; Inert atmosphere; Sealed tube; UV-irradiation; | 74 %Spectr. |
Conditions | Yield |
---|---|
toluene-4-sulfonic acid | 88.2% |
toluene-4-sulfonic acid In toluene for 12h; Heating; | 88% |
Conditions | Yield |
---|---|
potassium hydroxide; copper In various solvent(s) at 160℃; for 8h; | 88% |
diphenylamine
chlorobenzene
A
N,N-diphenylaminobenzene
B
N-(2-biphenyl)aniline
Conditions | Yield |
---|---|
With 2,2,6,6-tetramethylpiperidinyl-lithium In diethyl ether; cyclohexane at 25℃; for 24h; Inert atmosphere; | A n/a B 87% |
Conditions | Yield |
---|---|
With CoCuFe2O4; potassium hydroxide In ethanol at 60℃; for 5h; Green chemistry; | 85% |
With potassium carbonate In ethanol; water at 70℃; for 8h; Chan-Lam Coupling; | 40 %Chromat. |
Conditions | Yield |
---|---|
With C46H58Br2N4O4Pd; potassium tert-butylate In 1,2-dimethoxyethane at 80℃; for 15h; Inert atmosphere; Buchwald-Hartwig amination; | A 84% B 16% |
With water; sodium t-butanolate In N,N-dimethyl-formamide at 120℃; for 3h; Schlenk technique; | A 40% B 60% |
With potassium tert-butylate; copper(l) iodide; tributylphosphine In toluene at 135℃; for 10.5h; Product distribution; Further Variations:; Catalysts; high pressure; |
Conditions | Yield |
---|---|
With potassium tert-butylate; urea; tri tert-butylphosphoniumtetrafluoroborate; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In 1,4-dioxane at 100℃; for 19h; | 83% |
With potassium tert-butylate; urea; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane at 100℃; for 19h; | 83% |
Multi-step reaction with 2 steps 1: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 96 h / Reflux 2: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 144 h / Reflux View Scheme |
Conditions | Yield |
---|---|
With potassium phosphate; bis(acetylacetonato)palladium(II); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine In n-heptane at 130℃; for 24h; Buchwald-Hartwig Coupling; Sealed tube; Inert atmosphere; | 83% |
With potassium phosphate; bis(acetylacetonato)palladium(II); BrettPhos In n-heptane at 130℃; for 24h; | 83% |
iodobenzene
copper
N,N-diphenylaminobenzene
Conditions | Yield |
---|---|
With potassium hydroxide; diphenylamine | 82% |
Conditions | Yield |
---|---|
With methanol; gold; hydrogen; caesium carbonate at 100℃; under 3800.26 Torr; for 132h; | 82% |
Conditions | Yield |
---|---|
With potassium hydroxide at 60℃; for 0.5h; Catalytic behavior; Green chemistry; | 81% |
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
A
N,N-diphenylaminobenzene
B
(E)-2-[(4-nitrophenyl)methylene]cyclohexanone
Conditions | Yield |
---|---|
Stage #1: 2-[10-(N-phenylamino)-1'-(4-nitrophenyl)]methylcyclohexanone; 2-(trimethylsilyl)phenyl trifluoromethanesulfonate With potassium fluoride; 18-crown-6 ether In acetonitrile at 20℃; Inert atmosphere; Stage #2: With hydrogenchloride In water; acetonitrile for 1h; Inert atmosphere; Reflux; | A 15% B 15% C 80% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; triethylamine In N,N-dimethyl-formamide at 20℃; | 100% |
With bromine In chloroform at 0 - 20℃; for 1h; | 97% |
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 12h; Cooling with ice; | 94% |
Conditions | Yield |
---|---|
With sodium nitrate; acetic acid In chloroform at 85℃; Inert atmosphere; | 100% |
With 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imide at 20℃; for 3h; Ionic liquid; | 89% |
With dinitrogen trioxide In dichloromethane at 0℃; | 42% |
N,N-diphenylaminobenzene
N,N,N',N'-tetraphenyl-4,4'-diaminobiphenyl
Conditions | Yield |
---|---|
Stage #1: N,N-diphenylaminobenzene With methanesulfonic acid In dichloromethane at 0℃; Stage #2: With chloranil In dichloromethane at 0 - 20℃; for 0.0166667h; Reagent/catalyst; Solvent; Time; | 99% |
With 5% rhodium-on-charcoal; trifluoroacetic acid at 50℃; for 1h; Reagent/catalyst; Green chemistry; regioselective reaction; | 99% |
Stage #1: N,N-diphenylaminobenzene With copper(II) perchlorate In acetonitrile at 25℃; for 12h; Stage #2: With potassium carbonate In water; acetonitrile at 25℃; for 0.5h; Further stages.; | 81% |
Conditions | Yield |
---|---|
Stage #1: N,N-diphenylaminobenzene With trifluorormethanesulfonic acid; [bis(pyridine)iodine]+ tetrafluoroborate In dichloromethane at 0 - 20℃; for 21h; Stage #2: With water; sodium thiosulfate In dichloromethane | 99% |
Stage #1: N,N-diphenylaminobenzene With trifluorormethanesulfonic acid; [bis(pyridine)iodine]+ tetrafluoroborate In dichloromethane at 0 - 20℃; for 21h; Stage #2: With sodium thiosulfate In dichloromethane; water | 99% |
With iodine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; | 97% |
N,N-diphenylaminobenzene
N,N-bis(4-bromophenyl)aniline
Conditions | Yield |
---|---|
With N-Bromosuccinimide In ethyl acetate at 20℃; for 24h; | 99% |
With N-Bromosuccinimide In ethyl acetate at 20℃; for 24h; | 99% |
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 4h; | 90% |
N,N-diphenylaminobenzene
Conditions | Yield |
---|---|
With C21H17F3OP(1+)*C32H12BF24(1-) In 1,2-dichloro-ethane at 20℃; for 0.0833333h; Friedel-Crafts Alkylation; | 99% |
Conditions | Yield |
---|---|
Stage #1: 1H-imidazole; N,N-diphenylaminobenzene In acetonitrile for 0.5h; Stage #2: trifluoroacetic anhydride In acetonitrile for 1.5h; | 98.32% |
N,N-diphenylaminobenzene
5-hexylbicyclo[2.2.1]hept-2-ene
Conditions | Yield |
---|---|
{(η6-toluene)Ni(C6F5)2} In toluene at 20℃; for 24h; | 98% |
N,N-diphenylaminobenzene
tris(phenyl-2,4,6-d3)amine
Conditions | Yield |
---|---|
With tris(pentafluorophenyl)borate; water-d2 In chloroform-d1 at 80℃; for 24h; Sealed tube; regioselective reaction; | 98% |
N,N-diphenylaminobenzene
N,N-dimethyl-formamide
4-(diphenylamino)benzaldehyde
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-formamide With trichlorophosphate In 1,2-dichloro-ethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: N,N-diphenylaminobenzene In 1,2-dichloro-ethane at 60℃; for 16h; Inert atmosphere; | 97.6% |
With trichlorophosphate at 35 - 40℃; Inert atmosphere; | 96% |
Stage #1: N,N-diphenylaminobenzene; N,N-dimethyl-formamide With trichlorophosphate In 1,2-dichloro-ethane at 0 - 45℃; Vilsmeier-Haack reaction; Stage #2: With water In 1,2-dichloro-ethane Vilsmeier-Haack reaction; Cooling with ice; | 96% |
Conditions | Yield |
---|---|
In water at 50℃; for 3h; | 97% |
N,N-diphenylaminobenzene
chloranil
A
2,3,5,6-tetrachlorobenzene-1,4-diol
B
N,N,N',N'-tetraphenyl-4,4'-diaminobiphenyl
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 0.0166667h; Molecular sieve; | A 96% B 83% |
Conditions | Yield |
---|---|
With trichlorophosphate In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Reflux; | 95% |
Stage #1: N,N-diphenylaminobenzene With trichlorophosphate In N,N-dimethyl-formamide for 1h; Stage #2: With sodium hydroxide | 85% |
With N,N-dimethyl-formamide; trichlorophosphate at 100℃; for 6h; | 52.74% |
N,N-diphenylaminobenzene
acetyl chloride
(1,1',1''-[nitrilotri(4,1-phenylene)]tri(ethan-1-one))
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 0 - 20℃; Friedel-Crafts Acylation; Inert atmosphere; | 95% |
With aluminum (III) chloride In dichloromethane at 0℃; for 12h; | 95% |
With aluminum (III) chloride In dichloromethane Reflux; | 92% |
N,N-diphenylaminobenzene
2,7-dibromo-(9-phenyl-9H-fluoren-9-ol)
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2h; Inert atmosphere; Schlenk technique; | 95% |
N,N-diphenylaminobenzene
4-N,N-diphenylamino-1-bromobenzene
Conditions | Yield |
---|---|
With N-Bromosuccinimide In tetrachloromethane for 4h; Reflux; | 94% |
With N-Bromosuccinimide In tetrachloromethane for 4h; Heating; | 93% |
With N-Bromosuccinimide In tetrachloromethane for 4h; Inert atmosphere; Reflux; | 93% |
Structure of Triphenylamine (CAS NO.603-34-9):
IUPAC Name: N,N-diphenylaniline
Empirical Formula: C18H15N
Molecular Weight: 245.3184
EINECS: 210-035-5
Index of Refraction: 1.646
Molar Refractivity: 80.09 cm3
Molar Volume: 220.5 cm3
Polarizability: 31.75×10-24cm3
Surface Tension: 47.2 dyne/cm
Density: 1.112 g/cm3
Flash Point: 157.3 °C
Enthalpy of Vaporization: 61.12 kJ/mol
Melting Point: 124-128 °C(lit.)
Boiling Point: 365 °C at 760 mmHg
Vapour Pressure: 1.62E-05 mmHg at 25°C
Water Solubility: insoluble
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
Physical Appearance: Crystals or off-white lumpy solid
Product Categories: Triphenylamine series;White crystalline powder;White Powder;Phenylamine Series;Dye Intermediate;Amines;C11 to C38;Nitrogen Compounds
Triphenylamine (CAS NO.603-34-9) is coated on film bases as primary photoconductor.
1. | orl-rat LD50:3200 mg/kg | 85INA8 Documentation of the Threshold Limit Values and Biological Exposure Indices. 5 (1986),612. | ||
2. | orl-mus LD50:1600 mg/kg | 85INA8 Documentation of the Threshold Limit Values and Biological Exposure Indices. 5 (1986),612. |
Reported in EPA TSCA Inventory.
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-28-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S28:After contact with skin, wash immediately with plenty of soap-suds.
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 2
RTECS: YK2680000
Hazard Note: Irritant
HS Code: 29214980
Moderately toxic by ingestion. When heated to decomposition it emits toxic fumes of NOx. See also AROMATIC AMINES.
OSHA PEL: TWA 5 mg/m3
ACGIH TLV: TWA 5 mg/m3
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