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4-(N,N-Diphenylamino)benzaldehyde is a key intermediate used in the synthesis of azines and azomethines for optoelectronic applications. It contributes to the distinct thermal, optical, and electrochemical properties of these compounds, with azines typically exhibiting higher melting points and lower LUMO levels compared to their azomethine counterparts. The compound's structural features influence solubility, processability, and photoluminescence behavior, making it valuable for designing materials with tunable optoelectronic properties.

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  • 4181-05-9 Structure
  • Basic information

    1. Product Name: 4-(N,N-Diphenylamino)benzaldehyde
    2. Synonyms: 4-(diphenylamino)-benzaldehyd;4-(DIPHENYLAMINO)BENZALDEHYDE;4-FORMYLTRIPHENYLAMINE;4-(N,N-DIPHENYLAMINO)BENZALDEHYDE;P-N,N-DIPHENYLAMINO-BENZALDEHYDE;P-FORMYLTRIPHENYLAMINE;4-(N,N-DIPHENYLAMINO)BENZALDEHYDE (P-) 98+%;4-Diphenylaminobenzaldehyde,98%
    3. CAS NO:4181-05-9
    4. Molecular Formula: C19H15NO
    5. Molecular Weight: 273.33
    6. EINECS: 1533716-785-6
    7. Product Categories: Aromatic Aldehydes & Derivatives (substituted);Triphenylamine series;Yellow crystalline powder;White Powder;Phenylamine Series;Pyrroles ,Pyrimidines
    8. Mol File: 4181-05-9.mol
  • Chemical Properties

    1. Melting Point: 129-133 °C(lit.)
    2. Boiling Point: 436.8 °C at 760 mmHg
    3. Flash Point: 171.2 °C
    4. Appearance: Pale yellow/Solid
    5. Density: 1.176 g/cm3
    6. Vapor Pressure: 7.84E-08mmHg at 25°C
    7. Refractive Index: 1.67
    8. Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
    9. Solubility: Soluble in methanol.
    10. PKA: -5.61±0.30(Predicted)
    11. Sensitive: Air Sensitive
    12. BRN: 2732795
    13. CAS DataBase Reference: 4-(N,N-Diphenylamino)benzaldehyde(CAS DataBase Reference)
    14. NIST Chemistry Reference: 4-(N,N-Diphenylamino)benzaldehyde(4181-05-9)
    15. EPA Substance Registry System: 4-(N,N-Diphenylamino)benzaldehyde(4181-05-9)
  • Safety Data

    1. Hazard Codes: Xi,Xn
    2. Statements: 36/37/38
    3. Safety Statements: 26-36
    4. WGK Germany: 3
    5. RTECS:
    6. F: 8
    7. TSCA: Yes
    8. HazardClass: N/A
    9. PackingGroup: N/A
    10. Hazardous Substances Data: 4181-05-9(Hazardous Substances Data)

4181-05-9 Usage

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.

Facile synthesis of triphenylamine and phenothiazine-based Schiff bases for aggregation-induced enhanced emission, white light generation, and highly selective and sensitive copper(ii) sensing

Anand, Vivek,Sadhasivam, Balaji,Dhamodharan, Raghavachari

, p. 18979 - 18990 (2018)

Two new Schiff bases, one triphenylamine-based (TPA-SB) and another phenothiazine-based (PTz-SB), were synthesized via facile reactions. Both molecules showed aggregation-induced enhanced emission (AIEE) properties. In fact, an 8-fold increase in the fluo

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.

A novel triphenylamine-based dye sensitizer supported on titania nanoparticles and the effect of titania fabrication on its optical properties

Moretti, Elisa,Aversa, Manuela,Scrivanti, Alberto,Storaro, Loretta,Talon, Aldo,Marin, Riccardo,Cecilia, Juan Antonio,Rodríguez-Castellón, Enrique,Polizzi, Stefano

, p. 218 - 230 (2015)

A new synthesised triphenylamine-based dye having a branched structure with one OH-ending branch able to interact with the surface hydroxyl moieties of mesoporous TiO2 is reported. Optical properties of the dye-titania hybrid material are presented and the higher efficiency of the dye on pure anatase TiO2 compared to the commercial Degussa P25, which contains a rutile phase component, is confirmed. The optical and chemical properties of the dye make it a promising candidate as a metal-free dye for DSSCs or as a host for a variety of transition or main group metal ions for different 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.

Detection of nitroaromatics based on aggregation induced emission of barbituric acid derivatives

Zhang, Han-Jun,Tian, Yan,Tao, Fu-rong,Yu, William,You, Kai-Yue,Zhou, Lin-Rui,Su, Xi,Li, Tian-duo,Cui, Yue-Zhi

, (2019)

Barbituric acid derivatives with typical aggregation induced emission (AIE) are reported. Their emission wavelengths varied with water fraction of their solution. UV–visible absorption spectroscopy and theoretical calculations revealed the intramolecular

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

Synthesis and characterization of a new pillar[5]arene-based [1]rotaxane

Tian, Huasheng,Wang, Chunyu,Lin, Po-Han,Meguellati, Kamel

, p. 3416 - 3422 (2018)

In this study, we reported the synthesis of three kinds of mono-functional pillar[5]arene derivatives PRI, PRII and R and their structures were studied by 1D and 2D NMR spectra and mass spectra. The 2D NMR spectra including 1H-13C HSQC, 1H-1H COSY and NOESY spectra indicated that PRI and PRII are both stable self-included pseudo[1]rotaxanes in CDCl3. These original structures are promising compounds for the design of pillar[5]-based [1]rotaxane. And the results showed that R could exist stable in CDCl3 and DMSO because of the coordination of N-H?O hydrogen bonding interaction and C-H?π interaction.

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

Axial-symmetric conjugated group promoting intramolecular charge transfer performances of triphenylamine sensitizers for dye-sensitized solar cells

Chen, Shaorui,Pei, Juan,Pang, Zhihan,Wu, Wenjun,Yu, Xudong,Zhang, Cong

, (2020)

The intramolecular charge transport (ICT) process directly determines the charge generation, transport, and even injection of the dye-sensitized solar cell (DSSC) sensitizer. Herein, we constructed a new series of D-π-A system by linking 4-methoxyphenyl and triphenylamine donors with an ethynyl group having an axial-symmetric conjugated system. Since the axisymmetric conjugate group overcomes the reduction of the conjugate characteristic caused by the plane distortion, the molecular ICT performance and the electronic recombination inhibition are effectively improved. As a result, the photoelectric conversion efficiency was increased from 3.43% to 6.37% by means of the extension of the π-bridge at same time. It provides a new idea for the design and development of DSSC sensitizers in the future.

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