615-50-9

Basic information

• Product Name: 2,5-Diaminotoluene sulfate
• Synonyms: 2-methyl-1,4-benzenediaminesulfate(1:1);2-methyl-p-phenylenediaminesulphate;4-benzenediamine,2-methyl-sulfate(1:1);c.i.76043;p-diaminotoluenesulfate;p-toluenediaminesulphate;p-toluylenediaminesulphate;p-tolylenediaminesulphate
• CAS NO: 615-50-9
• Molecular Formula: C₇H₁₀N₂*H₂O₄S
• Molecular Weight: 220.25
• EINECS: 210-431-8
• Product Categories: Intermediates of Dyes and Pigments;Organic Chemicals
• Mol File: 615-50-9.mol
• Article Data: 0

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 273.7 °C at 760 mmHg
• Flash Point: 140.6 °C
• Appearance: powder
• Density: 1366[at 20℃]
• Vapor Pressure: 0.00565mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: 9.6g/l
• PKA: 6.39[at 20 ℃]
• Water Solubility: soluble
• BRN: 3755478
• CAS DataBase Reference: 2,5-Diaminotoluene sulfate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Diaminotoluene sulfate(615-50-9)
• EPA Substance Registry System: 2,5-Diaminotoluene sulfate(615-50-9)

Safety Data

• Hazard Codes: T,N
• Statements: 20/21-25-43-51/53
• Safety Statements: 24-37-45-61
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: XT0525000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 615-50-9(Hazardous Substances Data)

Usage

Chemical Properties

White Redish Powder

Uses

2,5-Diaminotoluene sulfate is a primary intermediate in various permanent hair dyes.

General Description

2,5-Diaminotoluene sulfate occurs as an intermediate during hair dye formulation.

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by ingestion and intraperitoneal routes. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also SULFATES.

InChI:InChI=1/C7H10N2.H2O4S/c1-5-4-6(8)2-3-7(5)9;1-5(2,3)4/h2-4H,8-9H2,1H3;(H2,1,2,3,4)

Synthetic route

2-methyl(p-phenylenediamine) dihydrogen sulfate (615-50-9) + Ethyl oxalyl chloride (4755-77-5) → Et2H2Meppba (1392473-01-6)

Conditions	Yield
With triethylamine In tetrahydrofuran for 1h; Reflux;	80%
With triethylamine In tetrahydrofuran at 0℃; for 1h; Reflux;	80%

1-(1-(tert-butoxycarbonyl)piperidin-4-yl)-1H-indazole-3-carboxylic acid + 2-methyl(p-phenylenediamine) dihydrogen sulfate (615-50-9) → tert-butyl 4-(3-((4-amino-3-methylphenyl)carbamoyl)-1H-indazol-1-yl)piperidine-1-carboxylate

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	79%

1-methyl-1H-indazole-3-carboxylic acid (50890-83-0) + 2-methyl(p-phenylenediamine) dihydrogen sulfate (615-50-9) → N-(4-amino-3-methylphenyl)-1-methyl-1H-indazole-3-carboxamide

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 72h; Inert atmosphere;	31.4%

1-chloroanthracene-9,10-dione (82-44-0) + 2-methyl(p-phenylenediamine) dihydrogen sulfate (615-50-9) → 1-(4-amino-2-methylphenylamino)anthraquinone + 1-(4-amino-3-methylphenylamino) anthraquinone

Conditions	Yield
With copper(l) iodide; potassium carbonate at 100℃; for 8h; Concentration; Temperature; Ullmann Condensation; Inert atmosphere; Supercritical conditions; Overall yield = 68.03 %;

3-amino-2,6-dimethyl-phenol (6994-64-5) + 2-methyl(p-phenylenediamine) dihydrogen sulfate (615-50-9) → C15H17N3O (30809-89-3) + C15H17N3O

Conditions	Yield
With potassium hexacyanoferrate(III) In aq. phosphate buffer at 30℃; pH=10.3; Kinetics; Mechanism; pH-value;

2-methyl(p-phenylenediamine) dihydrogen sulfate (615-50-9) + m-Hydroxyaniline (591-27-5) → C13H13N3O + C13H13N3O

Conditions	Yield
With potassium hexacyanoferrate(III) In aq. phosphate buffer at 30℃; pH=10.3; Kinetics; pH-value;

2-methyl(p-phenylenediamine) dihydrogen sulfate (615-50-9) → 2-Methyl-1,4-benzochinondiimin (4377-75-7)

Conditions	Yield
With potassium hexacyanoferrate(III) In aq. phosphate buffer at 25℃; pH=7.9; Kinetics; pH-value;

1-methyl-1H-indazole-3-carboxylic acid (50890-83-0) + 2-methyl(p-phenylenediamine) dihydrogen sulfate (615-50-9) → N-(4-(6-methoxypyrazolo[1,5-a]pyridine-3-carboxamido)-3-methylphenyl)-1-methyl-1H-indazole-3-carboxamide

Conditions	Yield
Multi-step reaction with 2 steps 1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 72 h / 20 °C / Inert atmosphere 2: trimethylaluminum / toluene / 20 - 90 °C / Inert atmosphere View Scheme

Downstream Products

• 30809-89-3 C₁₅H₁₇N₃O 
• 1392473-01-6 Et₂H₂Meppba