Product Name

  • Name

    4-(N,N-Diphenylamino)benzaldehyde

  • EINECS 628-054-6
  • CAS No. 4181-05-9
  • Article Data136
  • CAS DataBase
  • Density 1.176 g/cm3
  • Solubility
  • Melting Point 129-133 °C(lit.)
  • Formula C19H15NO
  • Boiling Point 436.8 °C at 760 mmHg
  • Molecular Weight 273.334
  • Flash Point 171.2 °C
  • Transport Information
  • Appearance Pale yellow powder
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 4181-05-9 (4-(N,N-Diphenylamino)benzaldehyde)
  • Hazard Symbols HarmfulXn, IrritantXi
  • Synonyms Benzaldehyde,p-(diphenylamino)- (7CI,8CI);4-(Diphenylamino)benzaldehyde;4-Formyltriphenylamine;p-(Diphenylamino)benzaldehyde;p-(N,N-Diphenylamino)benzaldehyde;p-Formyl-N,N-diphenylaniline;
  • PSA 20.31000
  • LogP 4.96890

Synthetic route

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

4-(diphenylamino)benzaldehyde
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%
4-(diphenylamino)benzonitrile
20441-00-3

4-(diphenylamino)benzonitrile

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

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

N,N-diphenylaminobenzene

4-(diphenylamino)benzaldehyde
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%
N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

triphenylphosphine
603-35-0

triphenylphosphine

4-(diphenylamino)benzaldehyde
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%
N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

B

4,4'-diformyltriphenylamine
53566-95-3

4,4'-diformyltriphenylamine

C

tris(4-formylphenyl)amine
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

4-formylphenyl diphenylcarbamate

4-(diphenylamino)benzaldehyde
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%
dichloromethane
75-09-2

dichloromethane

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

acetone
67-64-1

acetone

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

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

N,N-diphenylaminobenzene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

B

4,4'-diformyltriphenylamine
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

bis(4-(diphenylamino)phenyl)methylium tetrafluoroborate

4-(diphenylamino)benzaldehyde
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%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

diphenylamine
122-39-4

diphenylamine

4-(diphenylamino)benzaldehyde
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%
[4-(diphenylamino)phenyl]methanol
25069-40-3

[4-(diphenylamino)phenyl]methanol

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
With eosin y In dimethyl sulfoxide at 80℃; for 24h; Irradiation;40%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
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
diphenylamine
122-39-4

diphenylamine

4-halogen-4'-methoxybiphenyl

4-halogen-4'-methoxybiphenyl

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
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
603-34-9

N,N-diphenylaminobenzene

A

4-[2 (triethoxysilyl) ethyl] triphenylamine
190334-72-6

4-[2 (triethoxysilyl) ethyl] triphenylamine

B

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
With trichlorophosphate In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethanol; water; N,N-dimethyl-formamide
Triethoxysilane
998-30-1

Triethoxysilane

N,N-diphenyl-N-(4-vinylphenyl)amine
25069-74-3

N,N-diphenyl-N-(4-vinylphenyl)amine

A

4-[2 (triethoxysilyl) ethyl] triphenylamine
190334-72-6

4-[2 (triethoxysilyl) ethyl] triphenylamine

B

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
In toluene
bromobenzene
108-86-1

bromobenzene

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
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
diphenylamine
122-39-4

diphenylamine

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
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
iodobenzene
591-50-4

iodobenzene

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
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
30388-31-9

2-cyano-3-(4-(diphenylamino)phenyl) acrylic acid

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
With water; iodine; lithium iodide In dichloromethane; acetonitrile at 20℃; for 300h;
4-(N,N-diphenylamino)benzyl bromide
183994-94-7

4-(N,N-diphenylamino)benzyl bromide

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
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
aniline
62-53-3

aniline

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
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
603-34-9

N,N-diphenylaminobenzene

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
With N,N-dimethyl-formamide Vilsmeier Reaction;
4-N,N-diphenylamino-1-bromobenzene
36809-26-4

4-N,N-diphenylamino-1-bromobenzene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere;
C50H69N3O4

C50H69N3O4

A

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

B

3,4,5-tri-O-(octyloxy)benzohydrazide
872140-54-0

3,4,5-tri-O-(octyloxy)benzohydrazide

Conditions
ConditionsYield
UV-irradiation;
C25H20N4O

C25H20N4O

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
With sodium hypochlorite; water In aq. phosphate buffer; dimethyl sulfoxide at 20℃; for 0.00833333h; pH=7.4; Solvent;
diphenylamine
122-39-4

diphenylamine

p-(iodophenyl)carboxaldehyde
15164-44-0

p-(iodophenyl)carboxaldehyde

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate at 70 - 120℃; for 13h;
4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

[4-(diphenylamino)phenyl]methanol
25069-40-3

[4-(diphenylamino)phenyl]methanol

Conditions
ConditionsYield
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
4181-05-9

4-(diphenylamino)benzaldehyde

diethyl (5-(thiophen-2-yl)thiophen-2-yl)methylphosphonate
253344-94-4

diethyl (5-(thiophen-2-yl)thiophen-2-yl)methylphosphonate

N,N-diphenyl-4-[(E)-2-(2,2'-bithien-5-yl)-1-ethenyl]aniline
253345-02-7

N,N-diphenyl-4-[(E)-2-(2,2'-bithien-5-yl)-1-ethenyl]aniline

Conditions
ConditionsYield
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
1286685-28-6

{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
4181-05-9

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
1286685-59-3

[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
ConditionsYield
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
1286685-34-4

{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
4181-05-9

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
1286685-62-8

[4-(2-{4-[7-(5,5-dimethyl-[1,3]dioxan-2-yl)-9,9-dioctyl-9H-fluoren-2-yl]phenyl}-vinyl)-phenyl]-diphenylamine

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 1h; Horner-Wadsworth-Emmons olefination; Inert atmosphere;100%
4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

acetic acid hydrazide
1068-57-1

acetic acid hydrazide

C21H19N3O
1471986-40-9

C21H19N3O

Conditions
ConditionsYield
With acetic acid In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere;100%
With trifluoroacetic acid In methanol at 60℃;320 mg
pyrrole
109-97-7

pyrrole

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

5-(4’-hydroxyphenyl)-10,15,20-tri(N,N-diphenylaminophenyl)porphyrin

5-(4’-hydroxyphenyl)-10,15,20-tri(N,N-diphenylaminophenyl)porphyrin

Conditions
ConditionsYield
With propionic acid for 5h; Reflux;100%
2-Methylbenzothiazole
120-75-2

2-Methylbenzothiazole

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

(E)-N-{4-[2-(benzothiazol-2-yl)vinyl]phenyl}-N-phenylaniline
1016164-01-4

(E)-N-{4-[2-(benzothiazol-2-yl)vinyl]phenyl}-N-phenylaniline

Conditions
ConditionsYield
With sodium hydroxide In methanol Heating;98%
diethyl (4-bromobenzyl)phosphonate
38186-51-5

diethyl (4-bromobenzyl)phosphonate

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

4-bromo-4′-(N,N′-diphenylamine)stilbene
925674-50-6

4-bromo-4′-(N,N′-diphenylamine)stilbene

Conditions
ConditionsYield
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
4181-05-9

4-(diphenylamino)benzaldehyde

4,4’-[(4-iodophenyl)amino]bis[benzaldehyde]
1548368-48-4

4,4’-[(4-iodophenyl)amino]bis[benzaldehyde]

Conditions
ConditionsYield
With potassium iodate; potassium iodide In acetic acid at 70℃; for 3h;98%
4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

N,N-bis(4-bromophenyl)aminobenzaldehyde
25069-38-9

N,N-bis(4-bromophenyl)aminobenzaldehyde

Conditions
ConditionsYield
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
4181-05-9

4-(diphenylamino)benzaldehyde

4,4'-bis(diethylphosphonomethyl)-2,2'-bipyridine
176220-38-5

4,4'-bis(diethylphosphonomethyl)-2,2'-bipyridine

4,4'-bis[(E)-2-(4-(diphenylamino)phenyl)ethenyl]-2,2'-bipyridyl

4,4'-bis[(E)-2-(4-(diphenylamino)phenyl)ethenyl]-2,2'-bipyridyl

Conditions
ConditionsYield
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
4181-05-9

4-(diphenylamino)benzaldehyde

4-[bis-(4-iodophenyl)amino]benzaldehyde
808758-81-8

4-[bis-(4-iodophenyl)amino]benzaldehyde

Conditions
ConditionsYield
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
4181-05-9

4-(diphenylamino)benzaldehyde

malononitrile
109-77-3

malononitrile

[4-(diphenylamino)phenyl]methylene-propanedinitrile
40703-88-6

[4-(diphenylamino)phenyl]methylene-propanedinitrile

Conditions
ConditionsYield
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
4181-05-9

4-(diphenylamino)benzaldehyde

4,4'-hydrazine-1,2-diylidenebis(methan-1-yl-1-ylidene)bis(N,N-diphenylaniline)
53338-51-5

4,4'-hydrazine-1,2-diylidenebis(methan-1-yl-1-ylidene)bis(N,N-diphenylaniline)

Conditions
ConditionsYield
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℃;
4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

chloroacetic acid
79-11-8

chloroacetic acid

C22H16N2O2S

C22H16N2O2S

Conditions
ConditionsYield
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%
4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

N,N-diphenylhydrazine hydrochloride
530-47-2

N,N-diphenylhydrazine hydrochloride

4-Diphenylaminobenzaldehyde diphenylhydrazone

4-Diphenylaminobenzaldehyde diphenylhydrazone

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 40 - 45℃; for 3h;95.4%
4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

diethyl 4-nitrobenzylphosphonate
2609-49-6

diethyl 4-nitrobenzylphosphonate

(E)-4-(4-nitrostyryl)-N,N-diphenylaniline
142677-07-4

(E)-4-(4-nitrostyryl)-N,N-diphenylaniline

Conditions
ConditionsYield
With sodium ethanolate In ethanol; N,N-dimethyl-formamide for 3h; Ambient temperature;95%
4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

methyl-triphenylphosphonium iodide
2065-66-9

methyl-triphenylphosphonium iodide

N,N-diphenyl-N-(4-vinylphenyl)amine
25069-74-3

N,N-diphenyl-N-(4-vinylphenyl)amine

Conditions
ConditionsYield
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%
4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

ethyl acetoacetate
141-97-9

ethyl acetoacetate

dimedone
126-81-8

dimedone

4-(4-diphenylamino-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester

4-(4-diphenylamino-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
With ammonium acetate; ytterbium(III) triflate In ethanol at 20℃; for 2h; Hantzsch reaction;95%
4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

4-Amino 3-nitro-benzonitrile
6393-40-4

4-Amino 3-nitro-benzonitrile

2-(4-(diphenylamino)phenyl)-1H-benzo[d]imidazole-5-carbonitrile
1476155-80-2

2-(4-(diphenylamino)phenyl)-1H-benzo[d]imidazole-5-carbonitrile

Conditions
ConditionsYield
With sodium dithionite In water; dimethyl sulfoxide at 120℃; for 4h;95%
4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

4-Nitrophenylene-1,2-diamine
99-56-9

4-Nitrophenylene-1,2-diamine

5-nitro-2-triphenylaminebenzimidazole
1585976-56-2

5-nitro-2-triphenylaminebenzimidazole

Conditions
ConditionsYield
With potassium iodide In N,N-dimethyl-formamide at 150℃; for 120h;95%
malonic acid
141-82-2

malonic acid

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

3-(4-(diphenylamino)phenyl)acrylic acid
25069-29-8

3-(4-(diphenylamino)phenyl)acrylic acid

Conditions
ConditionsYield
With piperidine; pyridine for 4h; Reflux;95%
With piperidine; pyridine for 3h; Reflux; Inert atmosphere; Schlenk technique;
4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

naphthalene-1,8-diamine
479-27-6

naphthalene-1,8-diamine

N-(4-(1H-perimidin-2-yl)phenyl)-N-phenylbenzenamine

N-(4-(1H-perimidin-2-yl)phenyl)-N-phenylbenzenamine

Conditions
ConditionsYield
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%
4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

N-methyl-4-methylpyridinium iodide
2301-80-6

N-methyl-4-methylpyridinium iodide

C26H23N2(1+)*I(1-)

C26H23N2(1+)*I(1-)

Conditions
ConditionsYield
With piperidine In ethanol for 4h; Reflux; Inert atmosphere;95%
4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

anthranilic acid amide
28144-70-9

anthranilic acid amide

2-(4-(diphenylamino)phenyl)quinazolin-4(3H)-one
1396108-98-7

2-(4-(diphenylamino)phenyl)quinazolin-4(3H)-one

Conditions
ConditionsYield
With sodium hydrogensulfite In N,N-dimethyl acetamide at 150℃; for 5h; Inert atmosphere;94.3%
1,4-phenylenediacetonitrile
622-75-3

1,4-phenylenediacetonitrile

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

(2Z,2'Z)-2,2'-(1,4-phenylene)bis(3-(4-(diphenylamino)phenyl)acrylonitrile)

(2Z,2'Z)-2,2'-(1,4-phenylene)bis(3-(4-(diphenylamino)phenyl)acrylonitrile)

Conditions
ConditionsYield
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%

4-(N,N-Diphenylamino)benzaldehyde Chemical Properties

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

4-(N,N-Diphenylamino)benzaldehyde 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

4-(N,N-Diphenylamino)benzaldehyde 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.

Post buying leads

About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia

Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog

©2008 LookChem.com,License: ICP

NO.:Zhejiang16009103

complaints:service@lookchem.com Desktop View