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% |
4-(diphenylamino)benzonitrile
4-(diphenylamino)benzaldehyde
Conditions | Yield |
---|---|
With diisobutylaluminium hydride In tetrahydrofuran; hexane at -78 - -20℃; for 7h; Reduction; | 95% |
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-dimethyl-formamide
triphenylphosphine
4-(diphenylamino)benzaldehyde
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-formamide With trichlorophosphate for 0.5h; Cooling with ice; Stage #2: triphenylphosphine at 55℃; for 1h; | 95% |
N,N-diphenylaminobenzene
N,N-dimethyl-formamide
A
4-(diphenylamino)benzaldehyde
B
4,4'-diformyltriphenylamine
C
tris(4-formylphenyl)amine
Conditions | Yield |
---|---|
With trichlorophosphate at 95℃; for 4h; Product distribution; Further Variations:; Temperatures; time; Vilsmeier-Haack formylation; | A 1% B 81% C 10% |
With trichlorophosphate for 0.0833333h; Vilsmeier-Haack reaction; Microwave irradiation; | A 60% B 20% C 20% |
With trichlorophosphate | A n/a B 57% C n/a |
With trichlorophosphate at 0 - 100℃; | A n/a B 57% C n/a |
With trichlorophosphate at 80℃; for 10h; |
4-(diphenylamino)benzaldehyde
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0) In toluene at 160℃; for 14h; Inert atmosphere; Sealed tube; Glovebox; | 80% |
dichloromethane
N,N-diphenylaminobenzene
acetone
4-(diphenylamino)benzaldehyde
Conditions | Yield |
---|---|
With sodium acetate trihydrate; magnesium sulfate; trichlorophosphate In methanol | 73% |
N,N-diphenylaminobenzene
N,N-dimethyl-formamide
A
4-(diphenylamino)benzaldehyde
B
4,4'-diformyltriphenylamine
Conditions | Yield |
---|---|
With trichlorophosphate at 95 - 100℃; for 6h; | A 3% B 71% |
With trichlorophosphate at 95℃; Vilsmeier-Haack Formylation; |
4-(diphenylamino)benzaldehyde
Conditions | Yield |
---|---|
With (4,4-dimethyl-2,6-dioxo-cyclohexyl)-phenyl-iodonium betaine In dichloromethane at 20℃; Kinetics; | 68% |
Conditions | Yield |
---|---|
Stage #1: 4-bromo-benzaldehyde With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate In toluene at 20℃; for 0.5h; Buchwald-Hartwig reaction; Inert atmosphere; Stage #2: diphenylamine With sodium t-butanolate In toluene at 110℃; for 24h; Inert atmosphere; | 63% |
[4-(diphenylamino)phenyl]methanol
4-(diphenylamino)benzaldehyde
Conditions | Yield |
---|---|
With eosin y In dimethyl sulfoxide at 80℃; for 24h; Irradiation; | 40% |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 78 percent / t-BuONa; 1,1'-bis(diphenylphosphanyl)ferrocene / Pd2(dba)3 / toluene / 8 h / 70 °C 2: 95 percent / DIBAL-H / tetrahydrofuran; hexane / 7 h / -78 - -20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 78 percent / t-BuONa; 1,1'-bis(diphenylphosphanyl)ferrocene / Pd2(dba)3 / toluene / 8 h / 70 °C 2: 95 percent / DIBAL-H / tetrahydrofuran; hexane / 7 h / -78 - -20 °C View Scheme |
N,N-diphenylaminobenzene
A
4-[2 (triethoxysilyl) ethyl] triphenylamine
B
4-(diphenylamino)benzaldehyde
Conditions | Yield |
---|---|
With trichlorophosphate In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethanol; water; N,N-dimethyl-formamide |
Triethoxysilane
N,N-diphenyl-N-(4-vinylphenyl)amine
A
4-[2 (triethoxysilyl) ethyl] triphenylamine
B
4-(diphenylamino)benzaldehyde
Conditions | Yield |
---|---|
In toluene |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium t-butanolate / toluene / 110 °C 2: trichlorophosphate View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate; sodium stearate; tetrabutylammomium bromide / water; ethanol / 100 °C 2: trichlorophosphate / 0 - 80 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium t-butanolate / toluene / 110 °C 2: trichlorophosphate View Scheme | |
Multi-step reaction with 2 steps 1.1: copper(I) oxide; sodium t-butanolate / 1-Methylpyrrolidine / 24 h / 90 °C / Inert atmosphere 2.1: trichlorophosphate / 10 °C / Inert atmosphere 2.2: 24 h / 35 °C / Inert atmosphere 2.3: Cooling with ice; Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: copper(I) oxide; sodium t-butanolate / 1-Methylpyrrolidine / 24 h / 90 °C / Inert atmosphere 2.1: trichlorophosphate / 10 °C / Inert atmosphere 2.2: 24 h / 35 °C / Inert atmosphere 2.3: Cooling with ice; Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: Cu catalyst / 3.5 h / 115 °C / Inert atmosphere 2: trichlorophosphate / 20 h / 0 - 100 °C / Inert atmosphere View Scheme |
2-cyano-3-(4-(diphenylamino)phenyl) acrylic acid
4-(diphenylamino)benzaldehyde
Conditions | Yield |
---|---|
With water; iodine; lithium iodide In dichloromethane; acetonitrile at 20℃; for 300h; |
4-(N,N-diphenylamino)benzyl bromide
4-(diphenylamino)benzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: eosin y; oxygen / dimethyl sulfoxide / 12 h / 25 °C / Irradiation 2: eosin y / dimethyl sulfoxide / 24 h / 80 °C / Irradiation View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; sodium stearate; tetrabutylammomium bromide / water; ethanol / 100 °C 2: trichlorophosphate / 0 - 80 °C View Scheme | |
Multi-step reaction with 2 steps 1: Cu catalyst / 3.5 h / 115 °C / Inert atmosphere 2: trichlorophosphate / 20 h / 0 - 100 °C / Inert atmosphere View Scheme |
N,N-diphenylaminobenzene
trichlorophosphate
4-(diphenylamino)benzaldehyde
Conditions | Yield |
---|---|
With N,N-dimethyl-formamide Vilsmeier Reaction; |
4-N,N-diphenylamino-1-bromobenzene
N,N-dimethyl-formamide
4-(diphenylamino)benzaldehyde
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere; |
A
4-(diphenylamino)benzaldehyde
B
3,4,5-tri-O-(octyloxy)benzohydrazide
Conditions | Yield |
---|---|
UV-irradiation; |
4-(diphenylamino)benzaldehyde
Conditions | Yield |
---|---|
With sodium hypochlorite; water In aq. phosphate buffer; dimethyl sulfoxide at 20℃; for 0.00833333h; pH=7.4; Solvent; |
diphenylamine
p-(iodophenyl)carboxaldehyde
4-(diphenylamino)benzaldehyde
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate at 70 - 120℃; for 13h; |
4-(diphenylamino)benzaldehyde
[4-(diphenylamino)phenyl]methanol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol; chloroform at 0 - 20℃; for 4h; | 100% |
With sodium tetrahydroborate; ethanol at 78℃; for 3h; | 99.2% |
With sodium tetrahydroborate In ethanol; dichloromethane at 20℃; for 1.2h; Large scale; | 99.9% |
4-(diphenylamino)benzaldehyde
diethyl (5-(thiophen-2-yl)thiophen-2-yl)methylphosphonate
N,N-diphenyl-4-[(E)-2-(2,2'-bithien-5-yl)-1-ethenyl]aniline
Conditions | Yield |
---|---|
With 15-crown-5; sodium hydride In tetrahydrofuran at 20℃; Wittig-Horner reaction; | 100% |
{4-[7-(5,5-dimethyl[1,3]dioxan-2-yl)2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl]-benzyl}phosphonic acid diethyl ester
4-(diphenylamino)benzaldehyde
[4-(2-{4-[7-(5,5-dimethyl[1,3]dioxan-2-yl)-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl]phenyl}-vinyl)-phenyl]-diphenyl-amine
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 1h; Horner-Wadsworth-Emmons olefination; Inert atmosphere; | 100% |
{4-[7-(5,5-dimethyl-[1,3]dioxan-2-yl)-9,9-dioctyl-9H-fluoren-2-yl]benzyl}phosphonic acid diethyl ester
4-(diphenylamino)benzaldehyde
[4-(2-{4-[7-(5,5-dimethyl-[1,3]dioxan-2-yl)-9,9-dioctyl-9H-fluoren-2-yl]phenyl}-vinyl)-phenyl]-diphenylamine
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 1h; Horner-Wadsworth-Emmons olefination; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With acetic acid In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; | 100% |
With trifluoroacetic acid In methanol at 60℃; | 320 mg |
Conditions | Yield |
---|---|
With propionic acid for 5h; Reflux; | 100% |
2-Methylbenzothiazole
4-(diphenylamino)benzaldehyde
(E)-N-{4-[2-(benzothiazol-2-yl)vinyl]phenyl}-N-phenylaniline
Conditions | Yield |
---|---|
With sodium hydroxide In methanol Heating; | 98% |
diethyl (4-bromobenzyl)phosphonate
4-(diphenylamino)benzaldehyde
4-bromo-4′-(N,N′-diphenylamine)stilbene
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere; | 98% |
With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere; | 87% |
With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere; | 87% |
4-(diphenylamino)benzaldehyde
4,4’-[(4-iodophenyl)amino]bis[benzaldehyde]
Conditions | Yield |
---|---|
With potassium iodate; potassium iodide In acetic acid at 70℃; for 3h; | 98% |
4-(diphenylamino)benzaldehyde
N,N-bis(4-bromophenyl)aminobenzaldehyde
Conditions | Yield |
---|---|
With N-Bromosuccinimide In N,N-dimethyl-formamide at -5 - 0℃; for 2h; Inert atmosphere; Darkness; | 97.41% |
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 25℃; Inert atmosphere; | 97.41% |
With N-Bromosuccinimide In tetrachloromethane at 80℃; for 6h; Inert atmosphere; | 90% |
4-(diphenylamino)benzaldehyde
4,4'-bis(diethylphosphonomethyl)-2,2'-bipyridine
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 20℃; for 5h; Horner-Wadsworth-Emmons olefination; | 97% |
With potassium tert-butylate In tetrahydrofuran at 70℃; for 24h; Horner-Wadsworth-Emmons olefination; Inert atmosphere; | 92% |
4-(diphenylamino)benzaldehyde
4-[bis-(4-iodophenyl)amino]benzaldehyde
Conditions | Yield |
---|---|
With potassium iodate; acetic acid; potassium iodide In water at 80℃; for 3h; | 96% |
With potassium iodate; potassium iodide In water; acetic acid at 80℃; for 5h; Inert atmosphere; | 96% |
With potassium iodate; acetic acid; potassium iodide at 85℃; for 5h; | 95% |
4-(diphenylamino)benzaldehyde
malononitrile
[4-(diphenylamino)phenyl]methylene-propanedinitrile
Conditions | Yield |
---|---|
With piperidine In ethanol at 20℃; for 1h; | 96% |
With sodium carbonate In neat (no solvent) | 94% |
With aluminum oxide In dichloromethane at 25℃; for 18h; Knoevenagel Condensation; | 89% |
4-(diphenylamino)benzaldehyde
4,4'-hydrazine-1,2-diylidenebis(methan-1-yl-1-ylidene)bis(N,N-diphenylaniline)
Conditions | Yield |
---|---|
With carbazic acid In neat (no solvent) Heating; | 96% |
With hydrazine hydrate In ethanol at 20℃; Inert atmosphere; | 87% |
With hydrazine hydrate In ethanol at 60 - 80℃; for 4h; | 81% |
With hydrazine hydrate at 20℃; for 3h; | 77% |
With hydrazine hydrate In ethanol at 80℃; |
Conditions | Yield |
---|---|
Stage #1: ammonium thiocyanate; chloroacetic acid In methanol; acetonitrile at 20℃; for 0.25h; Stage #2: 4-(diphenylamino)benzaldehyde With ammonium acetate In methanol; acetonitrile at 20℃; for 12h; stereoselective reaction; | 96% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 40 - 45℃; for 3h; | 95.4% |
4-(diphenylamino)benzaldehyde
diethyl 4-nitrobenzylphosphonate
(E)-4-(4-nitrostyryl)-N,N-diphenylaniline
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol; N,N-dimethyl-formamide for 3h; Ambient temperature; | 95% |
4-(diphenylamino)benzaldehyde
methyl-triphenylphosphonium iodide
N,N-diphenyl-N-(4-vinylphenyl)amine
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20℃; | 95% |
Stage #1: methyl-triphenylphosphonium iodide With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 0.25h; Stage #2: 4-(diphenylamino)benzaldehyde In tetrahydrofuran at 0 - 20℃; for 3h; Wittig reaction; | 89% |
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 4h; | 79% |
Conditions | Yield |
---|---|
With ammonium acetate; ytterbium(III) triflate In ethanol at 20℃; for 2h; Hantzsch reaction; | 95% |
4-(diphenylamino)benzaldehyde
4-Amino 3-nitro-benzonitrile
2-(4-(diphenylamino)phenyl)-1H-benzo[d]imidazole-5-carbonitrile
Conditions | Yield |
---|---|
With sodium dithionite In water; dimethyl sulfoxide at 120℃; for 4h; | 95% |
4-(diphenylamino)benzaldehyde
4-Nitrophenylene-1,2-diamine
5-nitro-2-triphenylaminebenzimidazole
Conditions | Yield |
---|---|
With potassium iodide In N,N-dimethyl-formamide at 150℃; for 120h; | 95% |
malonic acid
4-(diphenylamino)benzaldehyde
3-(4-(diphenylamino)phenyl)acrylic acid
Conditions | Yield |
---|---|
With piperidine; pyridine for 4h; Reflux; | 95% |
With piperidine; pyridine for 3h; Reflux; Inert atmosphere; Schlenk technique; |
Conditions | Yield |
---|---|
Stage #1: 4-(diphenylamino)benzaldehyde; naphthalene-1,8-diamine In isopropyl alcohol at 50℃; for 20h; Stage #2: With sodium metabisulfite In water; isopropyl alcohol at 50℃; for 1.5h; | 95% |
Conditions | Yield |
---|---|
With piperidine In ethanol for 4h; Reflux; Inert atmosphere; | 95% |
4-(diphenylamino)benzaldehyde
anthranilic acid amide
2-(4-(diphenylamino)phenyl)quinazolin-4(3H)-one
Conditions | Yield |
---|---|
With sodium hydrogensulfite In N,N-dimethyl acetamide at 150℃; for 5h; Inert atmosphere; | 94.3% |
Conditions | Yield |
---|---|
With potassium tert-butylate In ethanol for 2h; Knoevenagel condensation; Heating; | 94% |
In methanol at 20℃; Knoevenagel Condensation; Reflux; | 86.3% |
With tetra(n-butyl)ammonium hydroxide In ethanol for 3h; Reflux; | 68.3% |
Molecular Structure of 4-(N,N-Diphenylamino)benzaldehyde (CAS NO.4181-05-9):
IUPAC Name: 4-(N-phenylanilino)benzaldehyde
Empirical Formula: C19H15NO
Molecular Weight: 273.3285
H bond acceptors: 2
H bond donors: 0
Freely Rotating Bonds: 4
Polar Surface Area: 20.31Å2
Index of Refraction: 1.67
Molar Refractivity: 86.84 cm3
Molar Volume: 232.2 cm3
Surface Tension: 51.8 dyne/cm
Density: 1.176 g/cm3
Flash Point: 171.2 °C
Enthalpy of Vaporization: 69.34 kJ/mol
Boiling Point: 436.8 °C at 760 mmHg
Vapour Pressure: 7.84E-08 mmHg at 25°C
Melting Point: 129-133 °C(lit.)
Product Categories: Aromatic Aldehydes & Derivatives (substituted); Triphenylamine series; Yellow crystalline powder; White Powder; Phenylamine Series
InChI
InChI=1/C19H15NO/c21-15-16-11-13-19(14-12-16)20(17-7-3-1-4-8-17)18-9-5-2-6-10-18/h1-15H
Smiles
O=Cc1ccc(N(c2ccccc2)c2ccccc2)cc1
Safety information of 4-(N,N-Diphenylamino)benzaldehyde (CAS NO.4181-05-9):
Hazard Codes: Xi,Xn
Risk Statements:
36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements:
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
WGK Germany: 3
F: 8
4-(N,N-Diphenylamino)benzaldehyde , with CAS number of 4181-05-9, can be called 4-(diphenylamino)benzaldehyde ; Benzaldehyde, 4- (diphenylamino)- ; benzaldehyde, 4-(diphenylamino)- . It is a pale yellow powder.
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