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Tris(4-aminophenyl)amine
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Name

Tris(4-aminophenyl)amine

 EINECS 227-791-7
CAS No. 5981-09-9 Density 1.276g/cm3
PSA 81.30000 LogP 5.64660
Solubility Slightly soluble in water. Melting Point 230 °C
Formula C18H18N4 Boiling Point 571.3°C at 760 mmHg
Molecular Weight 290.368 Flash Point 294.1°C
Transport Information N/A Appearance Yellow Crystalline Solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 5981-09-9 (TAPA) Hazard Symbols N/A
Synonyms

1,4-Benzenediamine,N,N-bis(4-aminophenyl)- (9CI);Triphenylamine, 4,4',4''-triamino- (7CI,8CI);4,4',4''-Triaminotriphenylamine;N,N-Bis(4-aminophenyl)-1,4-benzenediamine;Tris(4-aminophenyl)amine;Tris(p-aminophenyl)amine;

Article Data 31

Tris(4-aminophenyl)amine Synthetic route

20440-93-1

tris(4-nitrophenyl)amine

5981-09-9

4,4',4-triaminotriphenylamine

Conditions
ConditionsYield
Stage #1: tris(4-nitrophenyl)amine With hydrogenchloride; tin In ethanol; water for 16h; Reflux;
Stage #2: With sodium hydroxide In water		95.7%
With palladium 10% on activated carbon; hydrazine hydrate In 1,4-dioxane; ethanol for 24.75h; Reflux;94%
With hydrogenchloride; tin In ethanol Reflux;94%
33331-95-2

1-N,1-N-bis(4-nitrophenyl)benzene-1,4-diamine

5981-09-9

4,4',4-triaminotriphenylamine

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrazine hydrate In tetrahydrofuran; ethanol for 16h; Reflux;85%
With hydrazine hydrate; palladium on activated charcoal In 1,4-dioxane; methanol at 80℃; for 3h; Inert atmosphere;82%
With hydrogenchloride; tin for 3h; Heating;78%
With tin(II) chloride dihdyrate In ethanol; acetonitrile Reflux; Inert atmosphere;
350-46-9

4-Fluoronitrobenzene

5981-09-9

4,4',4-triaminotriphenylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 65 percent / K2CO3 / dimethylsulfoxide / 72 h / 90 °C
2: 78 percent / Sn; aq. HCl / 3 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / dimethyl sulfoxide / 90 °C
2: tin(II) chloride dihdyrate / acetonitrile; ethanol / Reflux; Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: cesium fluoride / dimethyl sulfoxide / 24 h / 120 °C
2: palladium 10% on activated carbon; hydrazine hydrate / ethanol / 9 h / Reflux
View Scheme
106-50-3

1,4-phenylenediamine

5981-09-9

4,4',4-triaminotriphenylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 65 percent / K2CO3 / dimethylsulfoxide / 72 h / 90 °C
2: 78 percent / Sn; aq. HCl / 3 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / dimethyl sulfoxide / 90 °C
2: tin(II) chloride dihdyrate / acetonitrile; ethanol / Reflux; Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / dimethyl sulfoxide / 72 h / 90 °C / Inert atmosphere; Schlenk technique
2: palladium on activated charcoal; hydrazine hydrate / methanol; 1,4-dioxane / 3 h / 80 °C / Inert atmosphere
View Scheme
100-01-6

4-nitro-aniline

Boc-NH-L-Phe-L-Ala-NH-NH-C6H4-resinAc-X

Boc-NH-L-Phe-L-Ala-NH-NH-C6H4-resinAc-X

5981-09-9

4,4',4-triaminotriphenylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 13 percent / K2CO3 / dimethylsulfoxide / 12 h / 145 - 150 °C
2: Sn; aq. HCl / ethanol / Heating
View Scheme
100-00-5

4-chlorobenzonitrile

5981-09-9

4,4',4-triaminotriphenylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 13 percent / K2CO3 / dimethylsulfoxide / 12 h / 145 - 150 °C
2: Sn; aq. HCl / ethanol / Heating
View Scheme
603-34-9

N,N-diphenylaminobenzene

5981-09-9

4,4',4-triaminotriphenylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / HNO3, HOAc
2: 63 percent / Sn, aq. HCl / 1 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: glacial acetic acidacidic; nitric acid
2: hydrochloride of tin dichloride
View Scheme
350-46-9

4-Fluoronitrobenzene

106-50-3

1,4-phenylenediamine

5981-09-9

4,4',4-triaminotriphenylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / dimethyl sulfoxide / 72 h / 90 °C
2: palladium 10% on activated carbon; hydrazine hydrate / tetrahydrofuran; ethanol / 16 h / Reflux
View Scheme
100-01-6

4-nitro-aniline

350-46-9

4-Fluoronitrobenzene

5981-09-9

4,4',4-triaminotriphenylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / dimethyl sulfoxide / 48 h / 120 °C / Inert atmosphere
2: palladium on activated charcoal; hydrazine hydrate / 1,4-dioxane / 49 h / 80 °C / Inert atmosphere
View Scheme
100-01-6

4-nitro-aniline

5981-09-9

4,4',4-triaminotriphenylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: cesium fluoride / dimethyl sulfoxide / 24 h / 120 °C
2: palladium 10% on activated carbon; hydrazine hydrate / ethanol / 9 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / dimethyl sulfoxide / 10 h / 130 °C
2: tin; hydrogenchloride / ethanol / Reflux
View Scheme

Tris(4-aminophenyl)amine Specification

The Tris(4-aminophenyl)amine with the cas number 5981-09-9 is also called N,N-Bis(4-aminophenyl)benzene-1,4-diamine. The IUPAC name is 4-N,4-N-bis(4-aminophenyl)benzene-1,4-diamine. Its EINECS registry number is 227-791-7. This chemical belongs to the following product categories: (1)Fluorescent Labels and Indicators; (2)Fluorescent Labels & Indicators. It is yellow crystalline solid. It is a fluorescent trifunctional highly symmetric probe and shows remarkably high nonlinear optical properties.

Properties Computed from Structure: (1)XLogP3-AA: 3.1; (2)H-Bond Donor: 3; (3)H-Bond Acceptor: 4; (4)Rotatable Bond Count: 3; (5)Exact Mass: 290.153147; (6)MonoIsotopic Mass: 290.153147; (7)Topological Polar Surface Area: 81.3; (8)Heavy Atom Count: 22; (9)Formal Charge: 0; (10)Complexity: 272; (11)Isotope Atom Count: 0; (12)Defined Atom StereoCenter Count: 0; (13)Undefined Atom StereoCenter Count: 0; (14)Defined Bond StereoCenter Count: 0; (15)Undefined Bond StereoCenter Count: 0; (16)Covalently-Bonded Unit Count: 1.

Preparation: This chemical can be prepared by tris-(4-nitro-phenyl)-amine. This reaction needs reagent hydrochloride of tin dichloride.

You can still convert the following datas into molecular structure:
(1)SMILES: N(c1ccc(N)cc1)(c1ccc(N)cc1)c1ccc(N)cc1
(2)InChI: InChI=1/C18H18N4/c19-13-1-7-16(8-2-13)22(17-9-3-14(20)4-10-17)18-11-5-15(21)6-12-18/h1-12H,19-21H2

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