3204-61-3

Basic information

• Product Name: 1,2,4,5-BenzenetetraMine
• Synonyms: 1,2,4,5-BenzenetetraMine;Benzene-1,2,4,5-tetraamine
• CAS NO: 3204-61-3
• Molecular Formula: C₆H₁₀N₄
• Molecular Weight: 138.1704
• Mol File: 3204-61-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 274-276 °C
• Boiling Point: 400.9±40.0 °C(Predicted)
• Appearance: /
• Density: 1.401±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 6.01±0.10(Predicted)
• CAS DataBase Reference: 1,2,4,5-BenzenetetraMine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4,5-BenzenetetraMine(3204-61-3)
• EPA Substance Registry System: 1,2,4,5-BenzenetetraMine(3204-61-3)

Safety Data

• Hazardous Substances Data: 3204-61-3(Hazardous Substances Data)

Usage

General Description

1,2,4,5-Benzenetetramine, also known as benzotetramine, is a crystalline organic compound with the chemical formula C6H10N4. It belongs to the class of organic compounds known as diamines and is primarily used as a curing agent in the production of epoxy resins and adhesives. Its chemical structure consists of a benzene ring with four amine functional groups attached at positions 1, 2, 4, and 5, hence the name. 1,2,4,5-Benzenetetramine is a versatile chemical with various industrial applications, including in the manufacturing of plastics, rubber, and coatings, as well as in the field of biotechnology for the synthesis of pharmaceuticals and agrochemicals. It is important to handle this compound with caution as it is considered toxic and may cause skin and eye irritation upon contact.

Synthetic route

1,3-diamino-4,6-dinitrobenzene (4987-96-6) → 1,2,4,5-tetraaminobenzene (3204-61-3)

Conditions	Yield
With hydrogenchloride; tin
With nickel; ethyl acetate Hydrogenation;
With tin(ll) chloride
With phenylhydrazine 1.) 120 deg C, 1 h, 2.) 160 deg C, 4 h;

1,2,4-triamino-5-nitro-benzene (6635-35-4) → 1,2,4,5-tetraaminobenzene (3204-61-3)

Conditions	Yield
With hydrogenchloride; tin

3,6-diimino-1,4-cyclohexadiene-1,4-diamine (24196-90-5) → 1,2,4,5-tetraaminobenzene (3204-61-3)

Conditions	Yield
durch Reduktionsmittel;

hydrogenchloride (7647-01-0) + 5,6-dinitro-benzo[1,2,5]oxadiazole 1-oxide (3524-09-2) + tin → 1,2,4,5-tetraaminobenzene (3204-61-3)

Conditions	Yield

hydrogenchloride (7647-01-0) + 1,3-diamino-4,6-dinitrobenzene (4987-96-6) + tin → 1,2,4,5-tetraaminobenzene (3204-61-3)

Conditions	Yield

1,5-dibromo-2,4-dinitrobenzene (24239-82-5) → 1,2,4,5-tetraaminobenzene (3204-61-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol; ammonia / 150 °C 2: tin (II)-chloride View Scheme

1,5-bis(acetylamino)-2,4-dinitrobenzene (42783-40-4) → 1,2,4,5-tetraaminobenzene (3204-61-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid 2: tin; hydrochloric acid View Scheme

1,3-diacetylaminobenzene (10268-78-7) → 1,2,4,5-tetraaminobenzene (3204-61-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: nitric acid / -2 - -1 °C 2: sulfuric acid 3: tin; hydrochloric acid View Scheme

1,2,4-triaminobenzene N1,N2,N4-triacetate (30120-73-1) → 1,2,4,5-tetraaminobenzene (3204-61-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid; potassium nitrate 2: methanol.hydrochloric acid 3: aqueous hydrochloric acid; tin View Scheme

N,N',N''-(5-nitro-benzene-1,2,4-triyl)-tris-acetamide (860557-34-2) → 1,2,4,5-tetraaminobenzene (3204-61-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol.hydrochloric acid 2: aqueous hydrochloric acid; tin View Scheme

1,2,3-trichlorobenzene (87-61-6) → 1,2,4,5-tetraaminobenzene (3204-61-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid; nitric acid / 5 h / 55 - 70 °C 2: ammonia / 1,2-dimethoxyethane / 8 h / 150 °C / 7500.75 Torr / Autoclave 3: 3% Pd/C; hydrogen / N,N-dimethyl-formamide / 8 h / 11251.1 Torr / Autoclave View Scheme

4,6-dinitro-2-chloro-1,3-phenylenediamine → 1,2,4,5-tetraaminobenzene (3204-61-3)

Conditions	Yield
With 3% Pd/C; hydrogen In N,N-dimethyl-formamide under 11251.1 Torr; for 8h; Autoclave;

1,5-difluoro-2,4-dinitrobenzene (327-92-4) + 1,2,4,5-tetraaminobenzene (3204-61-3) → 4,6,16,18-tetranitro-10,12,22,24-tetraamino-2,8,14,20-tetraazacalix[4]arene (1446420-46-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 0℃; for 21h; Inert atmosphere; Reflux;	94%
With N-ethyl-N,N-diisopropylamine In acetonitrile	92%

1,2,4,5-tetraaminobenzene (3204-61-3) + benzil (134-81-6) → 2,3,6,7-tetraphenylpyrazino<2,3-g>quinoxaline (80829-03-4)

Conditions	Yield
With toluene-4-sulfonic acid In neat (no solvent) for 3h; Milling; Green chemistry;	90%

1,2,4,5-tetraaminobenzene (3204-61-3) + C26H28F2N8O8 → C32H36N12O8

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; Sealed tube; Inert atmosphere; Reflux;	83%

1,10-phenanthroline-5,6-dione (27318-90-7) + 1,2,4,5-tetraaminobenzene (3204-61-3) → 11,12-diaminodipyrido[3,2-a:2′,3′-c]phenazine (176649-65-3)

Conditions	Yield
at 78℃; for 0.0833333h;	79%
Stage #1: 1,10-phenanthroline-5,6-dione; 1,2,4,5-tetraaminobenzene With Amberlyst 15 In ethanol for 1h; Heating; Stage #2: With sodium hydroxide In methanol	11%

1,3-dimethyl-2-imidazolidinone (80-73-9) + 1,2,4,5-tetraaminobenzene (3204-61-3) → N1,N2,N4,N5-tetrakis(1,3-dimethylimidazolidin-2-ylidene)benzene-1,2,4,5-tetraamine (1258956-31-8)

Conditions	Yield
Stage #1: 1,3-dimethyl-2-imidazolidinone With oxalyl dichloride In CH3Cl at 80℃; for 20h; Inert atmosphere; Stage #2: 1,2,4,5-tetraaminobenzene With triethylamine In acetonitrile at 0℃; Inert atmosphere; Stage #3: With sodium hydroxide In water	74%

1,2,4,5-tetraaminobenzene (3204-61-3) + salicylaldehyde (90-02-8) → 2,2’,2’’,2’’’-[1,2,4,5-benzenetetrayltetrakis-(nitrilomethylidyne)]tetrakisphenole (19691-23-7)

Conditions	Yield
In ethanol; chloroform at 80℃; for 8h;	73.52%

1,2,4,5-tetraaminobenzene (3204-61-3) + 3,7-dipropyl-3,6-cycloheptadiene-1,2,5-trione (125309-58-2) → 1,5,9,13-tetrapropyl-dicyclohepta<5,6:b>pyrazino<2,3-g>quinoxaline-3,11-dione (125309-51-5)

Conditions	Yield
	71%

1,2,4,5-tetraaminobenzene (3204-61-3) + C34H44F2N8O8 → C40H52N12O8

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; Sealed tube; Reflux;	70%

1,2,4,5-tetraaminobenzene (3204-61-3) + 4,6-dipropyl-3,6-cycloheptadiene-1,2,5-trione (125309-57-1) → 2,4,10,12-tetrapropyl-dicyclohepta<5,6:b>pyrazino<2,3-g>quinoxaline-3,11-dione (125309-52-6)

Conditions	Yield
	68%

3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) + 1,2,4,5-tetraaminobenzene (3204-61-3) → 2,4-di-tert-butyl-6-((2,4,5-tri-[(3,5-di-tert-butyl-2-hydroxy-benzylidene)-amino]-phylimino)-methyl)-phenol

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; orthoformic acid triethyl ester In ethanol at 70℃; Inert atmosphere;	65%

2-dimethoxymethyl-6-quinolinecarboxaldehyde (439814-99-0) + 1,2,4,5-tetraaminobenzene (3204-61-3) + p-benzoquinone (106-51-4) → 5,6-dichloro-2-(2-formylquinoline-6-yl)benzimidazole (439815-00-6)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; ethanol; water	58%

5-dimethoxymethyl-1-(4-methylphenyl)sulfonylindole-2-carboxaldehyde (439815-03-9) + 1,2,4,5-tetraaminobenzene (3204-61-3) + p-benzoquinone (106-51-4) → 5,6-dichloro-2-[5-formyl-1-(4-methylphenyl)sulfonylindol-2-yl]benzimidazole (439815-04-0)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; ethanol; water	57%

cobalt(II) tetrafluoroborate hexahydrate + 1,2,4,5-tetraaminobenzene (3204-61-3) + [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] (22031-12-5) → (μ-1,2,4,5-benzenetetraamidato)bis[(1,1,1-tris(diphenylphosphanomethyl)ethane)cobalt(III)] bis(tetrafluoroborate), solvate with dichloromethane

Conditions	Yield
In tetrahydrofuran; ethanol (inert atmosphere); stirring (1 h); solvent removal (vac.), washing (Et2O; cold EtOH, Et2O), recrystn. (CH2Cl2/Et2O); elem. anal.;	53%

C62H74N2O4 (1033318-98-7) + 1,2,4,5-tetraaminobenzene (3204-61-3) → C130H150N8O4 (1033319-03-7)

Conditions	Yield
In 3-methyl-phenol at 50 - 180℃; twofold condensation 1,2-diamine with 1,2-diketone;	51%

5,6-dichloro-2-[2,5-dimethyl-6-[(2,4-dioxothiazolidin-5-ylidene)methyl]pyridin-3-yl]benzimidazole + 5-dimethoxymetyl-3,6-dimethyl-2-pyridinecarboxaldehyde (439814-95-6) + 1,2,4,5-tetraaminobenzene (3204-61-3) + p-benzoquinone (106-51-4) → 5,6-dichloro-2-(5-formyl-3,6-dimethylpyridin-2-yl)benzimidazole (439814-97-8)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; methanol; water	50%

C54H58N2O4 (1033318-95-4) + 1,2,4,5-tetraaminobenzene (3204-61-3) → C114H118N8O4 (1033319-01-5)

Conditions	Yield
In 3-methyl-phenol at 50 - 180℃; for 26h; twofold condensation 1,2-diamine with 1,2-diketone;	46%

3,6-Cycloheptadien-1,2,5-trion (56561-57-0) + 1,2,4,5-tetraaminobenzene (3204-61-3) → dicyclohepta<5,6:b>pyrazino<2,3-g>quinoxaline-3,11-dione (114459-05-1)

Conditions	Yield
	45%

1,2,4,5-tetraaminobenzene (3204-61-3) + 1,14-bisformyl-5,10-dimesityl-16-thiatripyrromethane (223921-77-5) → C74H70N8S2

Conditions	Yield
In methanol; benzene	43%

C64H74N4O4 (1033319-23-1) + 1,2,4,5-tetraaminobenzene (3204-61-3) → C134H150N12O4

Conditions	Yield
In 3-methyl-phenol at 50 - 180℃; twofold condensation 1,2-diamine with 1,2-diketone;	42%

C56H58N4O4 (1033319-21-9) + 1,2,4,5-tetraaminobenzene (3204-61-3) → C118H118N12O4

Conditions	Yield
In 3-methyl-phenol at 50 - 180℃; twofold condensation 1,2-diamine with 1,2-diketone;	40%

1,2,4,5-tetraaminobenzene (3204-61-3) + 5-formylisophthalic acid diethyl ester (208450-84-4) → C32H30N4O8

Conditions	Yield
Stage #1: 1,2,4,5-tetraaminobenzene With sodium hydroxide In ethanol at 20℃; for 2.5h; Inert atmosphere; Stage #2: 5-formylisophthalic acid diethyl ester With zirconium(IV) chloride In ethanol at 90℃; for 18h; Inert atmosphere; Stage #3: In ethanol for 24h; Reflux;	38%

1,2,4,5-tetraaminobenzene (3204-61-3) + 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane → C6H10N4*C12F4N4

Conditions	Yield
In methanol; N,N-dimethyl-formamide	35%

1,2,4,5-tetraaminobenzene (3204-61-3) + C13H8Cl4O2 (42788-09-0) → C32H18Cl8N4

Conditions	Yield
With triethylamine In ethanol for 2h; Heating;	21%

3,4-dioxo-hexanedicarboxylic acid diethyl ester (3249-69-2) + 1,2,4,5-tetraaminobenzene (3204-61-3) → pyrazino[2,3-g]quinoxaline-2,3,7,8-tetrayl-tetra-acetic acid tetraethyl ester

Conditions	Yield
With hydrogenchloride; ethanol; sodium acetate at 50 - 60℃;

1,2,4,5-tetraaminobenzene (3204-61-3) + dimethylglyoxal (431-03-8) → 1,2,7,8-tetramethylpyrazino<2,3-g>quinoxaline (111076-18-7)

Conditions	Yield
With hydrochloride of sodium acetate; water

1,2,4,5-tetraaminobenzene (3204-61-3) + benzil (134-81-6) → 2,3-diphenyl-quinoxaline-6,7-diamine (102007-61-4)

Conditions	Yield

1,2,4,5-tetraaminobenzene (3204-61-3) + <(+)-camphor>-quinone → 1,11,11-trimethyl-1,2,3,4-tetrahydro-1,4-methano-phenazine-7,8-diyldiamine

Conditions	Yield
nicht ganz rein erhalten;

Upstream product

• 4987-96-6 1,3-diamino-4,6-dinitrobenzene 
• 6379-46-0 1,2,3-trichloro-4,6-dinitrobenzene 
• 87-61-6 1,2,3-trichlorobenzene 
• 860557-34-2 N,N',N''-(5-nitro-benzene-1,2,4-triyl)-tris-acetamide 
• 30120-73-1 1,2,4-triaminobenzene N¹,N²,N⁴-triacetate 
• 10268-78-7 1,3-diacetylaminobenzene 
• 42783-40-4 1,5-bis(acetylamino)-2,4-dinitrobenzene 
• 24239-82-5 1,5-dibromo-2,4-dinitrobenzene 
• 7647-01-0 hydrogenchloride 
• 3524-09-2 5,6-dinitro-benzo[1,2,5]oxadiazole 1-oxide 
• 24196-90-5 3,6-diimino-1,4-cyclohexadiene-1,4-diamine 
• 6635-35-4 1,2,4-triamino-5-nitro-benzene 

Downstream Products

• 19691-23-7 2,2’,2’’,2’’’-[1,2,4,5-benzenetetrayltetrakis-(nitrilomethylidyne)]tetrakisphenole 
• 1572528-28-9 C₁₈H₁₂F₂N₈O₈ 
• 1258956-31-8 N₁,N₂,N₄,N₅-tetrakis(1,3-dimethylimidazolidin-2-ylidene)benzene-1,2,4,5-tetraamine 
• 1117964-61-0 2',2'',2''',2'''-(benzene-1,2,4,5-tetrayl)tetrakis(1,1,3,3-tetramethylguanidine) 
• 1033319-03-7 C₁₃₀H₁₅₀N₈O₄ 
• 1033319-01-5 C₁₁₄H₁₁₈N₈O₄ 
• 439815-04-0 5,6-dichloro-2-[5-formyl-1-(4-methylphenyl)sulfonylindol-2-yl]benzimidazole 
• 604812-16-0 C₃₈H₆₂N₈O₁₂ 
• 125309-54-8 2,3-diphenylcycloheptapyrazino<2,3-g>quinoxalin-9-one 
• 80829-03-4 2,3,6,7-tetraphenylpyrazino<2,3-g>quinoxaline 

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