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4181-05-9

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4181-05-9 Usage

Chemical Properties

Pale yellow powder

Uses

It is used as pharmaceutical intermediate.

Check Digit Verification of cas no

The CAS Registry Mumber 4181-05-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,1,8 and 1 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 4181-05:
(6*4)+(5*1)+(4*8)+(3*1)+(2*0)+(1*5)=69
69 % 10 = 9
So 4181-05-9 is a valid CAS Registry Number.
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

4181-05-9 Well-known Company Product Price

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  • Alfa Aesar

  • (H64887)  4-(Diphenylamino)benzaldehyde, 98%   

  • 4181-05-9

  • 1g

  • 206.0CNY

  • Detail
  • Alfa Aesar

  • (H64887)  4-(Diphenylamino)benzaldehyde, 98%   

  • 4181-05-9

  • 5g

  • 772.0CNY

  • Detail
  • Alfa Aesar

  • (H64887)  4-(Diphenylamino)benzaldehyde, 98%   

  • 4181-05-9

  • 25g

  • 3087.0CNY

  • Detail

4181-05-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-(N,N-Diphenylamino)benzaldehyde

1.2 Other means of identification

Product number -
Other names 4-Diphenylaminobenzaldehyde

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4181-05-9 SDS

4181-05-9Synthetic 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%

4181-05-9Relevant articles and documents

Fluorophore-functionalized graphene oxide with application in cell imaging

Lei, Lei,Ma, Hengchang,Yang, Manyi,Qin, Yanfang,Ma, Yucheng,Wang, Tao,Yang, Yuan,Lei, Ziqiang,Lu, Dedai,Guan, Xiaolin

, p. 12375 - 12379 (2017)

In this work, we fabricated a novel triphenylamine-derivative (DNDT)-modified nanographene oxide by following a simple gram-scale method. The product showed interesting optical properties and good potential for use in bioimaging applications. This fluorescent carbon material could be readily internalized by HepG2 cells and was clearly visualized to accumulate mainly in the nucleus.

Novel D-π-A type triphenylamine based chromogens for DSSC: Design, synthesis and performance studies

Hosseinzadeh, Behzad,Beni, Alireza Salimi,Azari, Masoumeh,Zarandi, Maryam,Karami, Marzeih

, p. 8371 - 8381 (2016)

In this work, four novel D-π-A organic dyes (MH, MT, DT, DH) consisting of triphenylamine as an electron donor and 2,4-thiazolidinedione/hydantoin as anchoring groups were designed and synthesized for use in dye-sensitized solar cells (DSSCs). The synthesized dyes were characterized using FT-IR, NMR, mass spectrometry, absorbance and electrochemical measurements. The photophysical, electrochemical and photovoltaic properties of the solar cells based on these dyes were investigated to study the effect of two different anchoring groups on the performance of the dye-sensitized solar cells. The dye consisting of two hydantoin anchoring groups shows the highest conversion efficiency of 2.70% (short-circuit current = 7.60 mA cm-2, open circuit voltage = 570 mV, and fill factor = 0.62 under standard AM1.5G irradiation) compared to the other designed dyes. The observed results will provide basic information for the future design of sensitizers with different anchoring groups for photovoltaic applications.

Triarylamine-Pyridine-Carbonitriles for Organic Light-Emitting Devices with EQE Nearly 40%

Chen, Yi-Kuan,Jayakumar, Jayachandran,Hsieh, Chia-Min,Wu, Tien-Lin,Liao, Chun-Cheng,Pandidurai, Jayabalan,Ko, Chang-Lun,Hung, Wen-Yi,Cheng, Chien-Hong

, (2021)

Highly efficient thermally activated delayed fluorescence (TADF) molecules are in urgent demand for solid-state lighting and full-color displays. Here, the design and synthesis of three triarylamine-pyridine-carbonitrile-based TADF compounds, TPAPPC, TPAmPPC, and tTPAmPPC, are shown. They exhibit excellent photoluminescence quantum yields of 79?100% with small ΔEST values, fast reverse intersystem crossing (RISC), and high horizontal dipole ratios (Θ//?= 86?88%) in the thin films leading to the enhancement of device light outcoupling. Consequently, a green organic light-emitting diode (OLED) based on TPAmPPC shows a high average external quantum efficiency of 38.8?± 0.6%, a current efficiency of 130.1?± 2.1?cd A–1, and a power efficiency of 136.3?± 2.2?lm W–1. The highest device efficiency of 39.8% appears to be record-breaking among TADF-based OLEDs to date. In addition, the TPAmPPC-based device shows superior operation lifetime and high-temperature resistance. It is worth noting that the TPA-PPC-based materials have excellent optical properties and the potential for making them strong candidates for TADF practical application.

Real-Time Fluorescence in Situ Visualization of Latent Fingerprints Exceeding Level 3 Details Based on Aggregation-Induced Emission

Wang, Ya-Long,Li, Chong,Qu, Hong-Qing,Fan, Cheng,Zhao, Peng-Ju,Tian, Rui,Zhu, Ming-Qiang

, p. 7497 - 7505 (2020)

A water-soluble probe, TPA-1OH, with aggregation-induced emission activity is synthesized and used for expedient real-time fluorescence in situ visualization of latent fingerprints (LFPs). A TPA-1OH aqueous solution exhibits nonfluorescence in pure water

Axial anchoring designed silicon-porphyrin sensitizers for efficient dye-sensitized solar cells

Liu, Jing,Yang, Xichuan,Sun, Licheng

, p. 11785 - 11787 (2013)

Using silicon as a central atom of porphyrin allows the introduction of axial ligands, which are not only employed to prevent the aggregation of the macrocycles but also anchor the dyes onto the TiO2 surface. A dye-sensitized solar cell with th

A triphenylamine-based benzoxazole derivative as a high-contrast piezofluorochromic material induced by protonation

Xue, Pengchong,Chen, Peng,Jia, Junhui,Xu, Qiuxia,Sun, Jiabao,Yao, Boqi,Zhang, Zhenqi,Lu, Ran

, p. 2569 - 2571 (2014)

A triphenylamine-based benzoxazole derivative exhibits a low contrast piezofluorochromic behavior under external pressure, and a high-contrast fluorescence change induced by protonation can be observed. The Royal Society of Chemistry 2014.

Novel triphenylamine-based fluorescent probe for specific detection and bioimaging of OCl?

Jiang, Yuliang,Zhang, Sheng,Wang, Bingxiang,Qian, Tao,Jin, Can,Wu, Shishan,Shen, Jian

, p. 5733 - 5738 (2018)

Hypochlorite (OCl?) plays important roles both in physiological and pathological processes, the detection of which is of great significance. Herein, a novel fluorescent probe based on the triphenylamine-type schiff base derivative (TPAD) was developed to detect OCl?. Probe TPAD exhibited specific fluorescence response toward ClO? with the fluorescence quenching rate up to 80%, and the detection limit was estimated to be 0.8 μM. The sensing mechanism study demonstrated that TPAD reacted with ClO? via an oxidation process, which was evidenced by MS and NMR characterization. Moreover, owing to the excellent sensing properties and negligible cytotoxicity, TPAD was successfully applied in the bioimaging of OCl? in living A549 cells.

Aggregation‐induced Emission Properties of Triphenylamine Chalcone Compounds

Zhang, Ying-Peng,Teng, Qi,Yang, Yun-Shang,Cao, Jing-Qi,Xue, Ji-Jun

, p. 807 - 815 (2021)

Two triphenylamine chalcone derivatives 1 and 2 were synthesized through the Vilsmeier-Haack reaction and Claisen-Schmidt condensation reaction. Through ultraviolet absorption spectroscopy and fluorescence emission spectroscopy experiments, it was confirmed that these two compounds exhibited good aggregation-induced emission (AIE) behavior in ethanol/water mixtures. The solvent effect test showed with the increase of the orientation polarizability of the solvent, the Stokes shift in the solvent of compound 1 and compound 2 shows a linear change trend. Through solid state fluorescence test and universal density function theory (DFT), the existence of π-π stacking interaction in the solid state of the compound has been studied, resulting in weak fluorescence emission. pH has no effect on the fluorescence intensity of the aggregate state of excited state intramolecular proton transfer (ESIPT) molecules in an acidic environment, but greatly weakens its fluorescence intensity in an alkaline environment. Cyclic voltammetry (CV) test shows that compound 1 was more prone to oxidation reaction than compound 2. The results of thermal stability test show that the thermal stability of compound 1 was better than that of compound 2, indicating that triphenylamine chalcone derivatives can improve the thermal stability of compounds by increasing the number of branches.

BF2 group chelated AIE fluorescent probe for polarity mapping of lipid droplets in cells and in vivo

Lai, Chaofeng,Zhao, Yuping,Liang, Yun,Zou, Xiang,Lin, Weiying

supporting information, (2021/12/02)

Lipid droplets (LDs), are multi-functional organelles with the storage of neutral lipids and proteins, participating in various of physiological processes. However, abnormal of LDs in morphology and numbers always lead to multiple diseases, including canc

A kind of AIE type triphenylamine derivative fluorescent probe and preparation method thereof and its application in the detection of hydrazine hydrate

-

Paragraph 0043; 0049-0052, (2022/01/10)

The present invention relates to an AIE type triphenylamine derivative fluorescent probe, chemically named (Z)-2- (4- (((E)4-(dimethylamino)benzene)3-(4-(diphenylamine)phenyl)acrylonitrile, the molecular formula is C36H30N4/sub

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