108-72-5

Basic information

• Product Name: 1,3,5-TRIAMINOBENZENE
• Synonyms: TIMTEC-BB SBB000049;1,3,5-TRIAMINOBENZENE;benzene-1,3,5-triamine;1,3,5-Benzenetriamine;3,5-Diaminoaniline;sym-Triaminobenzene;Trienathoin;1,3,5-triaMine Benzene
• CAS NO: 108-72-5
• Molecular Formula: C₆H₉N₃
• Molecular Weight: 123.16
• EINECS: 203-610-7
• Mol File: 108-72-5.mol
• Article Data: 41

Chemical Properties

• Melting Point: 84-85℃
• Boiling Point: 219.27°C (rough estimate)
• Flash Point: 230.2°C
• Appearance: /
• Density: 1.279
• Vapor Pressure: 2.16E-06mmHg at 25°C
• Refractive Index: 1.5589 (estimate)
• PKA: 5.05±0.10(Predicted)
• CAS DataBase Reference: 1,3,5-TRIAMINOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-TRIAMINOBENZENE(108-72-5)
• EPA Substance Registry System: 1,3,5-TRIAMINOBENZENE(108-72-5)

Safety Data

• Hazardous Substances Data: 108-72-5(Hazardous Substances Data)

Usage

Chemical Properties

Solid. Soluble in water, acetone, and alcohol; insoluble in ether, cold benzene, carbon tetrachloride, and petroleum ether. Combustible.

Uses

Ion-exchange resin intermediate, wetting and frothing agents, photographic developers, organic reactions.

InChI:InChI=1/C6H9N3/c7-4-1-5(8)3-6(9)2-4/h1-3H,7-9H2

Synthetic route

1,3,5-trinitrobenzene (99-35-4) → 1,3,5-triaminobenzene (108-72-5)

Conditions	Yield
With hydrogen; nickel In ethyl acetate at 40℃; under 30002.4 Torr; for 12h;	100%
With hydrogenchloride; tin das Zinnchloruerdoppelsalz entsteht;
With nickel; ethyl acetate Hydrogenation;

3, 5-dinitroaniline (618-87-1) → 1,3,5-triaminobenzene (108-72-5)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol under 30002.4 Torr;	100%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 3375.34 Torr; for 24h; Autoclave;	100%
With hydrogen; palladium on activated charcoal In tetrahydrofuran under 3800 Torr;	99%

3,5-dibromoaniline (626-40-4) → 1,3,5-triaminobenzene (108-72-5)

Conditions	Yield
With C24H12Cu2F9N4O7; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 140℃; for 16h;	100%

1,3,5-trisbromobenzene (626-39-1) → 1,3,5-triaminobenzene (108-72-5)

Conditions	Yield
With C24H12Cu2F9N4O7; tetrabutylammomium bromide; ammonia; caesium carbonate In water; ethylene glycol at 110 - 140℃; for 16h;	90%

2,4,6-Trinitrophenol (88-89-1) → 1,3,5-triaminobenzene (108-72-5)

Conditions	Yield
With ammonium formate; zinc In methanol at 60℃; for 1h;	85.8%

tri-tert-butyl N',N'',N'''-1,3,5-triaminobenzenetricarbamate → 1,3,5-triaminobenzene (108-72-5)

Conditions	Yield
With hydrogenchloride In ethanol; water	75%

2,4,6-trinitrochlorobenzene (88-88-0) → 1,3,5-triaminobenzene (108-72-5)

Conditions	Yield
With hydrogenchloride; tin das Zinnchloruerdoppelsalz entsteht;
With hydrogenchloride; iron at 60℃;

(1Z)-cyclohexane-1,3,5-trione trioxime (621-22-7) → 1,3,5-triaminobenzene (108-72-5)

Conditions	Yield
With hydrogen; nickel In acetic acid butyl ester at 80℃; for 3h; Yield given;
With palladium 10% on activated carbon; hydrogen In methanol for 8h; Solvent; Reagent/catalyst;

hydrogenchloride (7647-01-0) + 1,3,5-trinitrobenzene (99-35-4) + tin → 1,3,5-triaminobenzene (108-72-5)

hydrogenchloride (7647-01-0) + 2,4,6-trinitrochlorobenzene (88-88-0) + iron turnings → 1,3,5-triaminobenzene (108-72-5)

Conditions	Yield
at 60℃;

1,3,5-triazido-benzene (13556-15-5) → 1,3,5-triaminobenzene (108-72-5)

Conditions	Yield
Stage #1: 1,3,5-triazido-benzene With hydrogenchloride; zinc In ethanol; water at 0℃; for 7h; Stage #2: With sodium hydroxide; water In ethanol Product distribution / selectivity;

urea (57-13-6) → 1,3,5-triaminobenzene (108-72-5)

Conditions	Yield
at 390℃; under 60006 Torr;

5-chloro-1,3-benzenediamine (33786-89-9) + ammonium hydroxide → 1,3,5-triaminobenzene (108-72-5)

Conditions	Yield
copper(I) chloride
copper(I) chloride

5-chloro-1,3-benzenediamine (33786-89-9) + ammonium hydroxide + copper(I) oxide (1317-39-1, 146060-06-2) → 1,3,5-triaminobenzene (108-72-5)

5-chloro-1,3-benzenediamine (33786-89-9) → 1,3,5-triaminobenzene (108-72-5)

Conditions	Yield
With ammonia; copper(I) chloride

3,5-dinitrobenzoic acid (99-34-3) → 1,3,5-triaminobenzene (108-72-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium azide; sulfuric acid / chloroform / 3 h / Reflux 2: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 24 h / 25 °C / 7600.51 Torr View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; sodium azide / chloroform / 5 h / 80 °C 2: hydrogen; 10% Pd/C / tetrahydrofuran / 3800.26 Torr View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; sodium azide / chloroform / 3 h / 25 - 80 °C 2: hydrogen; palladium 10% on activated carbon / tetrahydrofuran; methanol / 24 h / 25 °C / 7600.51 Torr View Scheme

2,4,6-trinitrobenzoic acid sodium salt → 1,3,5-triaminobenzene (108-72-5)

Conditions	Yield
With 1% Pd on activated carbon; hydrogen In water at 49.84℃; under 3750.38 Torr; Mechanism; Autoclave;

2,4,6-trinitrobenzoic acid sodium salt → 1,3,5-triaminobenzene (108-72-5) + (1Z)-cyclohexane-1,3,5-trione trioxime (621-22-7) + 3,5-bis(hydroxyamino)aniline + 5-(hydroxyamino)benzene-1,3-diamine + 1,3,5-tris(hydroxyamino)benzene (98096-07-2) + (1E,3E,5E)-cyclohexane-1,3,5-trione trioxime

Conditions	Yield
With 5% Pd/C; hydrogen In water at 49.84℃; under 3750.38 Torr; Autoclave;	A 14 %Spectr. B 9 %Spectr. C 5 %Spectr. D 11 %Spectr. E 1 %Spectr. F 60 %Spectr.

2,4,6-trinitrobenzoic acid (129-66-8) → 1,3,5-triaminobenzene (108-72-5)

Conditions	Yield
Stage #1: 2,4,6-trinitrobenzoic acid With sodium hydrogencarbonate In water Stage #2: With 0.5% Pd/Sibunit carbon material; hydrogen In water at 69.84℃; under 3750.38 Torr; Catalytic behavior; Temperature; Autoclave;
With palladium on activated charcoal; hydrogen

2,4,6-trinitrobenzoic acid sodium salt → 1,3,5-triaminobenzene (108-72-5) + 2,4-diamino-6-nitrobenzoic acid + 2,6-diamino-4-hydroxyaminobenzoic acid + 2,4-diamino-6-[(3,5-diaminophenyl)-N,N,O-azoxy]benzoic acid + N1-(3,5-diaminophenyl)benzene-1,3,5-triamine + 2,8,14‐triazatetracyclo[13.3.1.13,7.19,13]henicosa‐1(19),3(21),4,6,9(20),10,12,15,17‐nonaene‐5,11,17‐triamine

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In water at 49.84℃; under 3750.38 Torr; Autoclave;

2,4,6-Trinitrotoluene (118-96-7) → 1,3,5-triaminobenzene (108-72-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid; potassium chlorate 2: palladium on activated charcoal; hydrogen View Scheme

maleic anhydride (108-31-6) + 1,3,5-triaminobenzene (108-72-5) → 1,3,5-tris(maleimido)benzene (21217-67-4)

Conditions	Yield
With cobalt(II) acetate; acetic anhydride; triethylamine In N,N-dimethyl-formamide at 50℃; for 20h; Inert atmosphere; Darkness;	98%

benzenediazonium (2684-02-8) + 1,3,5-triaminobenzene (108-72-5) → 2,4,6-trisazophenyl-1,3,5-triaminobenzene

Conditions	Yield
In water	97%

3,3,7-trimethyl-oct-6-enal (17920-90-0) + 1,3,5-triaminobenzene (108-72-5) → N,N',N''-Tris-[3,3,7-trimethyl-oct-6-en-(E)-ylidene]-benzene-1,3,5-triamine

Conditions	Yield
With 4 A molecular sieve In tetrahydrofuran for 24h; Ambient temperature;	96%

4-methyleneoxetan-2-one (674-82-8) + 1,3,5-triaminobenzene (108-72-5) → 1,3,5-trisacetoacetamidobenzene (892403-13-3)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 50℃; for 2h;	92.8%
In N,N-dimethyl-formamide at 20℃; for 12h;	29%

1,3,5-triaminobenzene (108-72-5) + 2,2'-Dichlorobiphenyl (13029-08-8) → 1,3,5-tris(9H-carbazol-9-yl)benzene (148044-07-9)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); C33H48N7P; sodium t-butanolate In toluene at 80℃; for 24h; Inert atmosphere; Schlenk technique; Glovebox;	92%

4-methylbenzene diazonium (57573-52-1) + 1,3,5-triaminobenzene (108-72-5) → 2,4,6-triazo-p-tolyl-1,3,5-triaminobenzene

Conditions	Yield
In water	91%

1,3,5-triaminobenzene (108-72-5) + 2,3-dimethoxybenzoyl chloride (7169-06-4) → 1,3,5-tris(2,3-dimethoxybenzamido)benzene

Conditions	Yield
With triethylamine In dichloromethane	88%
With triethylamine In dichloromethane

6-[4-[(4-methoxyphenyl)azo]phenoxy]hexanoyl chloride (1204522-60-0) + 1,3,5-triaminobenzene (108-72-5) → 1,3,5-tris{[6-[4-[(4-methoxyphenyl)azo]phenoxy]hexanoyl]amino}benzene (1204522-51-9)

Conditions	Yield
With triethylamine; lithium chloride In 1-methyl-pyrrolidin-2-one at 20℃;	87%

1,3,5-triaminobenzene (108-72-5) + 6-hexyl-2-hydroxy-1-naphtaldehyde → C57H63N3O3

Conditions	Yield
With acetic acid In ethanol Reflux;	85%

1,3,5-triaminobenzene (108-72-5) + 4-chlorophenylhydrazine hydrochloride (1073-70-7) → 1,3,5-triamino-2-(4'-chlorophenyl)benzene

Conditions	Yield
With air In dimethyl sulfoxide at 25℃; for 24h;	82%

1,3,5-triaminobenzene (108-72-5) + acetic anhydride (108-24-7) → N,N,N-triacetyl-1,3,5-triaminobenzene (26243-62-9)

Conditions	Yield
In ethanol at 30℃; for 3h;	82%

1,3,5-triaminobenzene (108-72-5) + benzoic acid anhydride (93-97-0) → N,N,N-tribenzoyl-1,3,5-triaminobenzene

Conditions	Yield
In methanol at 0℃; for 20h;	81%

1,3,5-triaminobenzene (108-72-5) + Ethyl oxalyl chloride (4755-77-5) → benzene-1,3,5-tris(oxamic acid) triethyl ester (67451-23-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 2h;	80%
With triethylamine In N,N-dimethyl-formamide

1,3,5-triaminobenzene (108-72-5) + 2-[2,6-Di-tert-butyl-5-(2,2-dimethyl-propionyl)-4-oxo-4H-[1,3]dioxin-2-yl]-4,4-dimethyl-pent-1-ene-1,3-dione (133753-22-7, 143948-92-9) → 1,3,5-tris-(1,3,5,7-tetra-t-butyl-2,6,9-trioxabicyclo[3.3.1]nona-3,7-dien-4-yl-carbonylamino)-benzene (693778-85-7)

Conditions	Yield
In tetrahydrofuran; acetonitrile at 20℃; for 240h;	80%

1,3,5-triaminobenzene (108-72-5) + 2-Methylpropionic anhydride (97-72-3) → 1,3,5-tris[2-methylpropionylamino]benzene (745070-67-1)

Conditions	Yield
In methanol at 100℃; for 5h;	80%

1,3,5-triaminobenzene (108-72-5) + benzenediazonium tetrafluoroborate (369-57-3) → 2,4,6-trisazophenyl-1,3,5-triaminobenzene

Conditions	Yield
In methanol at 25℃; for 0.166667h;	79.2%

1,3,5-triaminobenzene (108-72-5) + 3,4,5-tris(dodec-1-yloxy)aniline (151237-05-7) → 2,4,6-tris((3,4,5-tris(dodecyloxy)phenyl)diazenyl)benzene-1,3,5-triamine

Conditions	Yield
Stage #1: 3,4,5-tris(dodec-1-yloxy)aniline With trifluoroacetic acid In dichloromethane at 0℃; for 0.166667h; Stage #2: With tert.-butylnitrite In dichloromethane at 0 - 5℃; for 1h; Stage #3: 1,3,5-triaminobenzene With potassium carbonate In dichloromethane at 0 - 20℃; for 12.15h;	79%

1,3,5-triaminobenzene (108-72-5) + Boc-Trp-OH (13139-14-5) → C54H63N9O9

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 48h;	74.6%

cycl-isopropylidene malonate (2033-24-1) + 1,3,5-triaminobenzene (108-72-5) + trimethyl orthoformate (149-73-5) → C27H27N3O12

Conditions	Yield
Stage #1: cycl-isopropylidene malonate; trimethyl orthoformate for 1h; Reflux; Stage #2: 1,3,5-triaminobenzene for 2h; Reflux;	71%

1,3,5-triaminobenzene (108-72-5) + 2,2-dimethylpropanoic anhydride (1538-75-6) → 1,3,5-tris(2,2-dimethylpropionylamino)benzene

Conditions	Yield
In methanol at 20℃; for 2h;	65%

1,3,5-triaminobenzene (108-72-5) + 4-methylbenzenediazonium tetrafluoroborate (459-44-9) → 2,4,6-triazo-p-tolyl-1,3,5-triaminobenzene

Conditions	Yield
In methanol at 20℃; for 0.333333h;	64.4%

1,3,5-triaminobenzene (108-72-5) + 4-methoxybenzenediazonium tetrafluoroborate (459-64-3) → 2,4,6-triazo-p-methoxyphenyl-1,3,5-triaminobenzene

Conditions	Yield
In methanol at 25℃; for 0.166667h;	64.2%

1,3,5-triaminobenzene (108-72-5) + 1,3-Dioxo-7-{4-[(E)-2-(2-trimethylsilanyl-ethoxycarbonyl)-vinyl]-phenyl}-1H,3H-benzo[de]isochromene-6-carboxylic acid 2-trimethylsilanyl-ethyl ester (199169-42-1) → C102H111N3O18Si6

Conditions	Yield
With zinc diacetate In toluene Heating;	64%

p-methoxybenzenediazonium (17333-79-8) + 1,3,5-triaminobenzene (108-72-5) → 2,4,6-triazo-p-methoxyphenyl-1,3,5-triaminobenzene

Conditions	Yield
In water	64%

Upstream product

• 7647-01-0 hydrogenchloride 
• 99-35-4 1,3,5-trinitrobenzene 
• 88-88-0 2,4,6-trinitrochlorobenzene 
• 57-13-6 urea 
• 33786-89-9 5-chloro-1,3-benzenediamine 
• 1317-39-1 copper(I) oxide 
• 99-34-3 3,5-dinitrobenzoic acid 
• 88-89-1 2,4,6-Trinitrophenol 
• 129-66-8 2,4,6-trinitrobenzoic acid 
• 621-22-7 (1Z)-cyclohexane-1,3,5-trione trioxime 
• 118-96-7 2,4,6-Trinitrotoluene 
• 626-40-4 3,5-dibromoaniline 
• 626-39-1 1,3,5-trisbromobenzene 
• 13556-15-5 1,3,5-triazido-benzene 

Downstream Products

• 7373-27-5 1,3,5-benzenetriisocyanate 
• 67451-23-4 benzene-1,3,5-tris(oxamic acid) triethyl ester 
• 955997-56-5 N,N,N',N',N'',N''-hexa(trifluoromethanesulfonyl)-benzene-1,3,5-triamine 
• 1204522-39-3 1,3,5-tris{[4-[4-(phenylazo)phenoxy]butyryl]amino}benzene 
• 1204522-41-7 1,3,5-tris{[4-[4-[(4-methoxyphenyl)azo]phenoxy]butyryl]amino}benzene 
• 1204522-43-9 1,3,5-tris{[4-[4-[(4-cyanophenyl)azo]phenoxy]butyryl]amino}benzene 
• 1204522-35-9 1,3,5-tris{[4-[(4-methoxyphenyl)azo]benzoyl]amino}benzene 
• 1262794-05-7 tert-butyl N-3,5-di-(2-methylmaleimido)phenylcarbamate 
• 1262794-07-9 3,5-di-(3-methylmaleimido)anilinium trifluoroacetate 
• 1262794-08-0 N-dansyl-3,5-di-(3-methylmaleimido)aniline 
• 1567824-99-0 N',N''',N'''''-benzene-1,3,5-triyltris[N,N-dimethyl-P-(trichloromethyl)(phosphonoselenoic diamide)] 
• 1567824-96-7 N',N''',N'''''-benzene-1,3,5-triyltris[N,N-dimethyl-P-(trichloromethyl)(phosphonous diamide)] 
• 3058-38-6 2,4,6-triamino-1,3,5-trinitrobenzene 

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