32432-55-6

Basic information

• Product Name: 3,5-Diamino-2,4,6-trimethylbenzenesulfonic acid
• Synonyms: 3,5-diamino-2,4,6-trimethyl-benzenesulfonicaci;diaminomesitylenesulfonicacid;2,4,6-TRIMETHYL-3,5-DIAMINOBENZENESULFONIC ACID;2,6-DIAMINOMESITYLENE-4-SULFONIC ACID;2,4-DIAMINO-3,5-DIMETHYL-6-SULFOTOLUENE;3,5-DIAMINO-2,4,6-TRIMETHYLBENZENESULFONIC ACID;3,5-DIAMINO-2,4,6-TRIMETHYLBENZENESULPHONIC ACID;M-XYLENE-5-CARBOXYLIC ACID
• CAS NO: 32432-55-6
• Molecular Formula: C9H14N2O3S
• Molecular Weight: 230.29
• EINECS: 207-876-5
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 32432-55-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 169-171 °C(lit.)
• Appearance: /
• Density: 1.3034 (rough estimate)
• Refractive Index: 1.6800 (estimate)
• Storage Temp.: 2-8°C
• PKA: -1.46±0.50(Predicted)
• CAS DataBase Reference: 3,5-Diamino-2,4,6-trimethylbenzenesulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Diamino-2,4,6-trimethylbenzenesulfonic acid(32432-55-6)
• EPA Substance Registry System: 3,5-Diamino-2,4,6-trimethylbenzenesulfonic acid(32432-55-6)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-25
• Safety Statements: 26-36-37/39-45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• RTECS: DG8734030
• Hazardous Substances Data: 32432-55-6(Hazardous Substances Data)

Usage

Chemical Properties

beige powder

InChI:InChI=1/C9H14N2O3S/c1-4-7(10)5(2)9(15(12,13)14)6(3)8(4)11/h10-11H2,1-3H3,(H,12,13,14)/p-1

Synthetic route

2,4-dinitromesitylene-6-sulfonic acid (33144-12-6) → 3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6)

Conditions	Yield
With sodium sulfate In sulfuric acid at 30 - 70℃; electrosynthesis (lead cathode, 3-7 A/dm3), pH 2.5-3;	98%
With selenium; carbon monoxide; sodium carbonate In water at 150℃; under 37503.8 Torr; for 5h; Time; Temperature; Pressure; Reagent/catalyst; Autoclave;	84.21%

sodium salt of/the/ 4.6-dinitro-mesitylene-sulfonic acid-(2) → 3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6)

Conditions	Yield
With iron; acetic acid
With sodium carbonate; iron(II) sulfate

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) → 3,5-bis((4,6-dichloro-1,3,5-triazine-2-yl)amino)-2,4,6-trimethylbenzenesulfonic acid sodium salt

Conditions	Yield
With sodium carbonate In acetone at 0℃; for 2h; pH=6;	86.8%

3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) + 4-(4,5-dihydro-3-methyl-5-oxo-1H-pyrazol-1-yl)benzenesulfonic acid (89-36-1) → C29H25N8O11S3(3-)*3Na(1+)

Conditions	Yield
Stage #1: 3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid With hydrogenchloride; sodium nitrite In water at 5℃; for 0.583333h; Stage #2: 4-(4,5-dihydro-3-methyl-5-oxo-1H-pyrazol-1-yl)benzenesulfonic acid With sodium acetate In ethyl acetate; N,N-dimethyl-formamide at 5℃; for 1h;	72%

C23H40N4 + 3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) → C55H87N12O3S(1-)*Na(1+)

Conditions	Yield
Stage #1: 3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid With hydrogenchloride; sodium nitrite In water at 5℃; for 0.583333h; Stage #2: C23H40N4 With sodium acetate In ethyl acetate; N,N-dimethyl-formamide at 5℃; for 1h;	69%

3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) + 5-oxo-1-(4-sulfophenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid (118-47-8) → C29H19N8O15S3(5-)*5Na(1+)

Conditions	Yield
Stage #1: 3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid With hydrogenchloride; sodium nitrite In water at 5℃; for 0.583333h; Stage #2: 5-oxo-1-(4-sulfophenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid With sodium acetate In ethyl acetate; N,N-dimethyl-formamide at 5℃; for 1h;	69%

2,6-bis(mesitylamino)-4-methylpyridine-3-carbonitrile + 3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) → C59H63N12O3S(1-)*Na(1+)

Conditions	Yield
Stage #1: 3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid With hydrogenchloride; sodium nitrite In water at 5℃; for 0.583333h; Stage #2: 2,6-bis(mesitylamino)-4-methylpyridine-3-carbonitrile With sodium acetate In ethyl acetate; N,N-dimethyl-formamide at 5℃; for 1h;	69%

2,6-bis((2,6-diethylphenyl)amino)-4-methylnicotinonitrile + 3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) → C67H79N12O3S(1-)*Na(1+)

Conditions	Yield
Stage #1: 3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid With hydrogenchloride; sodium nitrite In water at 5℃; for 0.583333h; Stage #2: 2,6-bis((2,6-diethylphenyl)amino)-4-methylnicotinonitrile With sodium acetate In ethyl acetate; N,N-dimethyl-formamide at 5℃; for 1h;	69%

3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) + edaravone (89-25-8) → C29H27N8O5S(1-)*Na(1+)

Conditions	Yield
Stage #1: 3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid With hydrogenchloride; sodium nitrite In water at 5℃; for 0.583333h; Stage #2: 3-methyl-1-phenylpyrazolin-5-(4H)-one With sodium acetate In ethyl acetate; N,N-dimethyl-formamide at 5℃; for 1h;	65%

3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) → C37H34N4O10S3(2-)*2Na(1+)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride In 1,2-dimethoxyethane at 150℃; for 6h;	19%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride In ethylene glycol at 150℃; for 6h;	19%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride In ethylene glycol at 150℃; for 6h;	19%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride In ethylene glycol at 150℃; for 6h;	19%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride In ethylene glycol at 150℃; for 6h;	19%

3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) → C37H34N4O10S3(2-)*2Na(1+)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride In ethylene glycol at 150℃; for 6h;	19%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride In 1,2-dimethoxyethane at 150℃; for 6h;	19%

3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) → C48H44N4O13S3(2-)*2Na(1+)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride / 1,2-dimethoxyethane / 6 h / 150 °C 2: N,N-dimethyl acetamide / 1.5 h / 0 - 5 °C 3: N,N-dimethyl acetamide / 1.5 h / 0 - 5 °C View Scheme

3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) → C45H48N6O12S3(2-)*2Na(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride / 1,2-dimethoxyethane / 6 h / 150 °C 2.1: N,N-dimethyl acetamide / 1.5 h / 0 - 20 °C 2.2: 0.5 h / 0 - 20 °C View Scheme

3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) → C58H62N11O17S5(3-)*3Na(1+)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride / ethylene glycol / 6 h / 150 °C 2.1: N,N-dimethyl acetamide / 2 h / 5 - 20 °C 3.1: thionyl chloride / 6 h / 65 °C 3.2: 5 - 10 °C / pH 7 View Scheme

3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) → C41H38N4O12S3(2-)*2Na(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride / ethylene glycol / 6 h / 150 °C 2: N,N-dimethyl acetamide / 2 h / 5 - 20 °C View Scheme

3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) → C45H46N4O12S3(2-)*2Na(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride / ethylene glycol / 6 h / 150 °C 2: N,N-dimethyl acetamide / 2 h / 5 - 20 °C View Scheme

3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) → C45H40N4O16S3(4-)*4Na(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride / ethylene glycol / 6 h / 150 °C 2: N,N-dimethyl acetamide / 2.15 h / 60 °C View Scheme

3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) → C47H46N4O20S5(2-)*2Na(1+)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride / ethylene glycol / 6 h / 150 °C 2: N,N-dimethyl acetamide / 2.15 h / 60 °C 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 5 - 20 °C View Scheme

3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) → C51H42N4O14S3(2-)*2Na(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1: zinc(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / ethylene glycol / 6 h / 150 °C 2: N,N-dimethyl acetamide / 1 h / 0 °C View Scheme

3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) → C53H42N6O18S3(4-)*4Na(1+)

Conditions	Yield
Multi-step reaction with 3 steps 1: zinc(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / ethylene glycol / 6 h / 150 °C 2: N,N-dimethyl acetamide / 1 h / 0 °C 3: sodium hydrogencarbonate / N,N-dimethyl acetamide / 6 h / 60 °C View Scheme

1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid (116-81-4) + 3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) → 1-amino-4-(2',4',6'-trimethyl-3'-amino-5'-sulfophenylamino)anthraquinone-2-sulfonic acid (24124-40-1)

Conditions	Yield
With 1,4,7,10-tetraazacyclododecane-1,3-diene; copper; sodium hydrogencarbonate; copper(l) chloride In water at 80 - 82℃; for 4h; pH=9; Reagent/catalyst; Solvent;
Stage #1: 1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid; 3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid With sodium hydrogencarbonate In water at 80 - 90℃; for 4h; pH=8.8; Stage #2: With hydrogenchloride In water at 40℃; for 0.5h; pH=2.8 - 3; Reagent/catalyst; pH-value;

3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) → C51H42N4O14S3(2-)*2Na(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride / ethylene glycol / 6 h / 150 °C 2: N,N-dimethyl acetamide / 1.5 h / 0 - 5 °C View Scheme

3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) → C51H44N6O12S3(2-)*2Na(1+)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride / ethylene glycol / 6 h / 150 °C 2: N,N-dimethyl acetamide / 1.5 h / 0 - 5 °C 3: N,N-dimethyl acetamide / 8 h / 100 °C View Scheme

3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) → C53H42N6O16S3(4-)*4Na(1+)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride / ethylene glycol / 6 h / 150 °C 2: N,N-dimethyl acetamide / 1.5 h / 0 - 5 °C 3: sodium hydrogencarbonate / water; methanol / 6 h / 80 °C View Scheme

3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) → C39H38N4O14S5(2-)*2Na(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride / ethylene glycol / 6 h / 150 °C 2: pyridine / 3 h / 23 °C View Scheme

3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) → C51H40N6O10S5(2-)*2Na(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride / ethylene glycol / 6 h / 150 °C 2: pyridine / 3 h / 23 °C View Scheme

3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) → C45H46N4O14S3(2-)*2Na(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride / ethylene glycol / 6 h / 150 °C 2: N,N-dimethyl acetamide / 2 h / 10 - 23 °C View Scheme

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid (116-81-4) + 3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) + 4-aminobenzene sulfonic acid (121-57-3) → C32H23ClN7O11S3(3-)*3Na(1+)

Conditions	Yield
Stage #1: 1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid at 80℃; for 2h; Green chemistry; Stage #2: 3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid With copper(ll) sulfate pentahydrate at 95℃; for 12h; Green chemistry; Stage #3: 1,3,5-trichloro-2,4,6-triazine; 4-aminobenzene sulfonic acid Concentration; Temperature; Green chemistry; Further stages;

1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid (116-81-4) + C5H7Cl2N5O3S + 3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid (32432-55-6) → C28H25ClN8O11S3(2-)*2Na(1+)

Conditions	Yield
Stage #1: 3,5-diamino-2,4,6-trimethylbenzene-1-sulfonic acid With sodium carbonate In water pH=7.5 - 8.5; Large scale; Stage #2: 1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid With copper; sodium carbonate; copper(II) sulfate; copper(l) chloride In water at 50 - 83℃; Large scale; Stage #3: C5H7Cl2N5O3S Large scale; Further stages;

Upstream product

• 33144-12-6 2,4-dinitromesitylene-6-sulfonic acid 

Downstream Products

• 24124-40-1 1-amino-4-(2',4',6'-trimethyl-3'-amino-5'-sulfophenylamino)anthraquinone-2-sulfonic acid 

Relevant articles and documents

Method for synthesizing M acid

The invention belongs to the field of chemical synthesis, and particularly relates to a method for synthesizing M acid. The method includes reacting 5-dinitro-2,4,6-trimethylbenzenesulfonic acid adopted as a raw material at a high temperature under high pressure with the presence of carbon monoxide gas by adopting water as a solvent, adopting selenium as a catalyst and adopting an alkali as a co-catalyst; performing stirring and filtration; adjusting pH with hydrochloric acid to precipitate a product; and performing suction filtration and recrystallization to obtain a target product. The moleratio of the 5-dinitro-2,4,6-trimethylbenzenesulfonic acid to the selenium is 100:2-10, the mole ratio of the 5-dinitro-2,4,6-trimethylbenzenesulfonic acid to the water is 1:111 to 1:667, and the moleratio of the 5-dinitro-2,4,6-trimethylbenzenesulfonic acid to the co-catalyst is 5:1 to 5:8. The alkali is an organic alkali or an inorganic alkali. The method adopts a high-pressure reaction in a one-pot reaction manner, and is low in equipment investment, simple and safe to operate, low in cost, capable of meeting requirements of green chemistry, economical, capable of phase transfer catalysis,and the like.

Novel water-soluble anthraquinone dyes

The invention relates to novel, water-soluble anthraquinone dyes which, in the form of the free acid, have the formula I STR1 in which X is halogen, R1 is an unbranched or branched alkyl radical having 4 to 8 carbon atoms, R2 and R3 independently of one another are an unbranched or branched alkyl radical having 1 to 4 carbon atoms, R4 is hydrogen, an unbranched or branched alkyl radical having 1 to 4 carbon atoms, a free or acylated amino group or a fibre-reactive radical bonded via an amino group, R5 is hydrogen or an unbranched or branched alkyl radical having 1 to 4 carbon atoms and R6 and R7 independently of one another are hydrogen, an unbranched or branched alkyl radical having 1-4 carbon atoms, a --SO3 H group, halogen or a radical of the formula --CH2 --NH--CO--Y, in which Y is an alkyl or alkenyl radical having 1 to 4 carbon atoms which is unsubstituted or substituted by one or two halogen atoms, or is a substituted or unsubstituted phenyl radical, with the proviso that at least one of the radicals R6 or R7 is a --SO3 H group.