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Basic Information
CAS No.: 4181-05-9
Name: 4-(N,N-Diphenylamino)benzaldehyde
Article Data: 136
Molecular Structure:
Molecular Structure of 4181-05-9 (4-(N,N-Diphenylamino)benzaldehyde)
Formula: C19H15NO
Molecular Weight: 273.334
Synonyms: Benzaldehyde,p-(diphenylamino)- (7CI,8CI);4-(Diphenylamino)benzaldehyde;4-Formyltriphenylamine;p-(Diphenylamino)benzaldehyde;p-(N,N-Diphenylamino)benzaldehyde;p-Formyl-N,N-diphenylaniline;
EINECS: 628-054-6
Density: 1.176 g/cm3
Melting Point: 129-133 °C(lit.)
Boiling Point: 436.8 °C at 760 mmHg
Flash Point: 171.2 °C
Appearance: Pale yellow powder
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
PSA: 20.31000
LogP: 4.96890
Synthetic route
603-34-9

N,N-diphenylaminobenzene

68-12-2, 33513-42-7

N,N-dimethyl-formamide

4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
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%
20441-00-3

4-(diphenylamino)benzonitrile

4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
With diisobutylaluminium hydride In tetrahydrofuran; hexane at -78 - -20℃; for 7h; Reduction;95%
603-34-9

N,N-diphenylaminobenzene

4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
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%
68-12-2, 33513-42-7

N,N-dimethyl-formamide

603-35-0

triphenylphosphine

4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate for 0.5h; Cooling with ice;
Stage #2: triphenylphosphine at 55℃; for 1h;
95%
603-34-9

N,N-diphenylaminobenzene

68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

4181-05-9

4-(diphenylamino)benzaldehyde

B

53566-95-3

4,4'-diformyltriphenylamine

C

119001-43-3

tris(4-formylphenyl)amine

Conditions
ConditionsYield
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 trichlorophosphateA 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-formylphenyl diphenylcarbamate

4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0) In toluene at 160℃; for 14h; Inert atmosphere; Sealed tube; Glovebox;80%
75-09-2

dichloromethane

603-34-9

N,N-diphenylaminobenzene

67-64-1

acetone

4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
With sodium acetate trihydrate; magnesium sulfate; trichlorophosphate In methanol73%
603-34-9

N,N-diphenylaminobenzene

68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

4181-05-9

4-(diphenylamino)benzaldehyde

B

53566-95-3

4,4'-diformyltriphenylamine

Conditions
ConditionsYield
With trichlorophosphate at 95 - 100℃; for 6h;A 3%
B 71%
With trichlorophosphate at 95℃; Vilsmeier-Haack Formylation;

bis(4-(diphenylamino)phenyl)methylium tetrafluoroborate

4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
With (4,4-dimethyl-2,6-dioxo-cyclohexyl)-phenyl-iodonium betaine In dichloromethane at 20℃; Kinetics;68%
1122-91-4

4-bromo-benzaldehyde

122-39-4

diphenylamine

4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
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%
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    4181-05-9

    4-Diphenylaminobenzaldehyde

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    4-(N,N-Diphenylamino)benzaldehyde Chemical Properties Melting point 129-133 °C (lit.) Boiling point 436.8±28.0 °C(Predicted) density 1.176±0.06 g/cm3(Predicted) solubility Soluble in methanol. pka -5.61±

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    4-(N,N-Diphenylamino)benzaldehyde

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    4-(N,N-Diphenylamino)benzaldehyde

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  • 4181-05-9  CAS NO.4181-05-9

  • Casno:

    4181-05-9

    4181-05-9 CAS NO.4181-05-9

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  • 4-Diphenylamino-benzaldehyde

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    4181-05-9

    4-Diphenylamino-benzaldehyde

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    4181-05-9

    4-(N,N-Diphenylamino)benzaldehyde

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    4-(N,N-Diphenylamino)benzaldehyde

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  • 4-(N,N-Diphenylamino)benzaldehyde cas no. 4181-05-9 98%

  • Casno:

    4181-05-9

    4-(N,N-Diphenylamino)benzaldehyde cas no. 4181-05-9 98%

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  • Casno:

    4181-05-9

    4-(N,N-Diphenylamino)benzaldehyde

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  • trans-Anethole

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    4181-05-9

    trans-Anethole

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  • Casno:

    4181-05-9

    4-(N,N-Diphenylamino)benzaldehyde

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  • 4-(N,N-Diphenylamino)Benzaldehyde

  • Casno:

    4181-05-9

    4-(N,N-Diphenylamino)Benzaldehyde

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Chemistry

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 Profile

Safety information of  4-(N,N-Diphenylamino)benzaldehyde (CAS NO.4181-05-9):
Hazard Codes:  IrritantXi,HarmfulXn
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

Specification

 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.