• Name

  TAPA

• EINECS 227-791-7
• CAS No. 5981-09-9
• Article Data31
• CAS DataBase
• Density 1.276g/cm³
• 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
• Appearance Yellow Crystalline Solid
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• 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;
• PSA 81.30000
• LogP 5.64660

Synthetic route

20440-93-1

tris(4-nitrophenyl)amine

5981-09-9

4,4',4-triaminotriphenylamine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

5981-09-9

4,4',4-triaminotriphenylamine

2-nitrophenyl isocyanate

2-nitrophenyl isocyanate

N,N',N"-(nitrilotri-4,1-phenylene)tris(2-nitrophenylurea)

Conditions

Conditions	Yield
In tetrahydrofuran for 6h; Reflux;	96%
In tetrahydrofuran Reflux;	93%

1121-60-4

pyridine-2-carbaldehyde

iron(II) triflate

5981-09-9

4,4',4-triaminotriphenylamine

C90H72Fe2N18(4+)*4CF3O3S(1-)

Conditions

Conditions	Yield
In acetonitrile at 50℃; for 6h; Sealed tube; Inert atmosphere; Schlenk technique;	95%

...Expand

5981-09-9

4,4',4-triaminotriphenylamine

silver perchlorate

64379-45-9

1,8-naphthyridine-2-carboxaldehyde

6C45H30N10*12Ag(1+)*12ClO4(1-)

Conditions

Conditions	Yield
In [D3]acetonitrile at 20℃; for 18h; Inert atmosphere; Sealed tube;	94%

...Expand

764-85-2

Nonanoyl chloride

5981-09-9

4,4',4-triaminotriphenylamine

N-{4-[bis(4-nonanamidophenyl)amino]phenyl}nonanamide

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran; dichloromethane at 0 - 20℃; for 1.25h; Inert atmosphere;	94%

5981-09-9

4,4',4-triaminotriphenylamine

54010-75-2

zinc trifluoromethanesulfonate

33795-37-8

1,10-phenanthroline-2-carboxyaldehyde

4C57H36N10*6Zn(2+)*12CF3O3S(1-)

Conditions

Conditions	Yield
In acetonitrile at 70℃;	93%

...Expand

55-22-1

pyridine-4-carboxylic acid

5981-09-9

4,4',4-triaminotriphenylamine

1460315-59-6

N,N',N''-(nitrilotris(4,1-phenylene))triisonicotinamide

Conditions

Conditions	Yield
With pyridine; phosphoric acid triphenyl ester for 48h; Reflux;	92.3%

5981-09-9

4,4',4-triaminotriphenylamine

4755-77-5

Ethyl oxalyl chloride

N,N’,N’’-tris(4-phenyl)aminetris(oxamate)

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 0℃; for 4h; Inert atmosphere; Reflux;	92%

5981-09-9

4,4',4-triaminotriphenylamine

C13H16N2O

29105-03-1

cadmium(II) triflate

4C57H60N10*4Cd(2+)*8CF3O3S(1-)

Conditions

Conditions	Yield
In acetonitrile at 70℃;	92%

...Expand

zinc(II) bis(tetrafluoroborate) hydrate

5981-09-9

4,4',4-triaminotriphenylamine

33795-37-8

1,10-phenanthroline-2-carboxyaldehyde

4C57H36N10*6Zn(2+)*12BF4(1-)

Conditions

Conditions	Yield
In acetonitrile at 70℃;	90%

...Expand

17746-05-3

undecanoyl chloride

5981-09-9

4,4',4-triaminotriphenylamine

C51H78N4O3

Conditions

Conditions	Yield
Stage #1: 4,4',4-triaminotriphenylamine With triethylamine In dichloromethane Stage #2: undecanoyl chloride In dichloromethane at 0 - 26.84℃; for 24h; Inert atmosphere;	89%

19437-26-4

2,2'-dipyridyl ketone

5981-09-9

4,4',4-triaminotriphenylamine

29105-03-1

cadmium(II) triflate

3C40H30N8*2Cd(2+)*4CF3O3S(1-)

Conditions

Conditions	Yield
In acetonitrile at 70℃;	89%

...Expand

24677-78-9

2,3-dihydroxybenzaldehyde

5981-09-9

4,4',4-triaminotriphenylamine

777096-05-6

N,N',N''-tri(2,3-dihydroxybenzylidene)-4,4',4''-triaminotriphenylamine

Conditions

Conditions	Yield
In methanol	85%

5981-09-9

4,4',4-triaminotriphenylamine

29105-03-1

cadmium(II) triflate

33795-37-8

1,10-phenanthroline-2-carboxyaldehyde

4C57H36N10*12CF3O3S(1-)*6Cd(2+)

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 16h;	83%

...Expand

5981-09-9

4,4',4-triaminotriphenylamine

139-85-5

3,4-dihydroxybenzaldehyde

C39H30N4O6

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; dichloromethane; water at 20℃; for 12h; Inert atmosphere; Darkness;	83%

5981-09-9

4,4',4-triaminotriphenylamine

7693-46-1

4-Nitrophenyl chloroformate

C39H27N7O12

Conditions

Conditions	Yield
In tetrahydrofuran for 6h; Reflux;	83%

5981-09-9

4,4',4-triaminotriphenylamine

C51H51Cl2N3PRu

C51H54Cl2N7Ru

Conditions

Conditions	Yield
In toluene at 50℃; for 24h;	82%

5981-09-9

4,4',4-triaminotriphenylamine

90-02-8

salicylaldehyde

C39H30N4O3

Conditions

Conditions	Yield
With acetic acid In ethanol for 5h; Reflux;	81.7%

5981-09-9

4,4',4-triaminotriphenylamine

7144-08-3

Cholesteryl chloroformate

C102H150N4O6

Conditions

Conditions	Yield
In tetrahydrofuran	81.7%

2493-84-7

p-octyloxybenzoic acid

5981-09-9

4,4',4-triaminotriphenylamine

C63H78N4O6

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran	81%

5981-09-9

4,4',4-triaminotriphenylamine

87199-17-5

4-formylphenylboronic acid,

C39H33B3N4O6

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water at 20℃; for 12h; Inert atmosphere; Darkness;	81%

5981-09-9

4,4',4-triaminotriphenylamine

5588-84-1

vanadium(V) oxytriisopropoxide

[N((p-C6H4)imidovanadium(V) triisopropoxide)3]

Conditions

Conditions	Yield
With NaH In octane	80%

5981-09-9

4,4',4-triaminotriphenylamine

79-10-7

acrylic acid

C36H42N4O12(1+)*3H3N*NO3(1-)

Conditions

Conditions	Yield
Stage #1: 4,4',4-triaminotriphenylamine; acrylic acid at 45 - 50℃; Stage #2: With ammonia In water at 50℃; for 0.5h; Stage #3: With silver nitrate In water at 50℃; for 2h;	79%

5981-09-9

4,4',4-triaminotriphenylamine

157980-09-1

3,4,5-tris(octyloxy)benzoic acid

C111H174N4O12

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran	79%

2312-15-4

p-dodecyloxybenzoic acid

5981-09-9

4,4',4-triaminotriphenylamine

C75H102N4O6

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran	79%

3506-51-2

Benzoyl acetaldehyde

5981-09-9

4,4',4-triaminotriphenylamine

C45H36N4O3

Conditions

Conditions	Yield
With acetic acid In ethanol at 80℃; for 12h;	79%

Tris(4-aminophenyl)amine Specification