53297-70-4

Basic information

• Product Name: 3-Methyl-4-aminobenzensulfonamide
• Synonyms: 3-METHYL-4-AMINOBENZENSULFONAMIDE;4-AMINO-3-METHYLBENZENESULPHONAMIDE;4-AMINO-3-METHYLBENZENSULFONAMIDE;Benzenesulfonamide, 4-amino-3-methyl- (9CI);4-Amino-3-methylbenzenesulphonamide 95%;3-METHYL-4-AMINOBENZENSULFONAMIDE 98+%;4-Amino-3-methylbenzenesulfonamide;BenzenesulfonaMide, 4-aMino-3-Methyl-
• CAS NO: 53297-70-4
• Molecular Formula: C₇H₁₀N₂O₂S
• Molecular Weight: 186.23
• Product Categories: SULFONAMIDE;Phenyls & Phenyl-Het;Miscellaneous;Phenyls & Phenyl-Het
• Mol File: 53297-70-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 174 °C
• Boiling Point: 409.3 °C at 760 mmHg
• Flash Point: 201.3 °C
• Appearance: /
• Density: 1.359 g/cm³
• Vapor Pressure: 6.56E-07mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 10.19±0.60(Predicted)
• CAS DataBase Reference: 3-Methyl-4-aminobenzensulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-4-aminobenzensulfonamide(53297-70-4)
• EPA Substance Registry System: 3-Methyl-4-aminobenzensulfonamide(53297-70-4)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 53297-70-4(Hazardous Substances Data)

Usage

General Description

3-Methyl-4-aminobenzensulfonamide is an organic compound that consists of a benzene ring with an amino group and a sulfonamide group attached to it. It is commonly used as a building block in the synthesis of pharmaceuticals, particularly in the production of sulfonamide-based drugs. 3-Methyl-4-aminobenzensulfonamide is known for its antibacterial properties and is widely used in the treatment of urinary tract infections, bacterial meningitis, and other bacterial infections. Additionally, it is also used in the manufacturing of dyes, pigments, and herbicides. Its chemical structure and properties make it a valuable component in the pharmaceutical and chemical industries.

InChI:InChI=1/C7H10N2O2S/c1-5-4-6(12(9,10)11)2-3-7(5)8/h2-4H,8H2,1H3,(H2,9,10,11)

Synthetic route

N-[4-(aminosulfonyl)-2-methylphenyl]acetamide (252562-03-1) → 4-amino-3-methylbenzenesulfonamide (53297-70-4)

Conditions	Yield
With hydrogenchloride In ethanol; water at 80℃;	100%
With hydrogenchloride; water In ethanol Reflux;	100%
Stage #1: N-[4-(aminosulfonyl)-2-methylphenyl]acetamide With hydrogenchloride In ethanol; water Heating / reflux; Stage #2: With sodium hydrogencarbonate In ethanol; water at 20℃;	93%
With hydrogenchloride
With hydrogenchloride In ethanol for 1h; Heating;

4-(acetylamino)-3-methylbenzenesulfonyl chloride (14988-21-7) → 4-amino-3-methylbenzenesulfonamide (53297-70-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: NH4OH / tetrahydrofuran / 0.33 h / 20 °C 2: aq. HCl / ethanol / 1 h / Heating View Scheme
Multi-step reaction with 2 steps 1: ammonium hydroxide / water; tetrahydrofuran / 1 h / 0 - 20 °C 2: hydrogenchloride; water / ethanol / Reflux View Scheme

sodium 4-(acetylamino)-3-methylbenzenesulfonate → 4-amino-3-methylbenzenesulfonamide (53297-70-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride / dimethylformamide / 2 h / -4 °C 2: NH4OH / tetrahydrofuran / 0.33 h / 20 °C 3: aq. HCl / ethanol / 1 h / Heating View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / N,N-dimethyl-formamide / 2 h / -40 - 20 °C 2: ammonium hydroxide / water; tetrahydrofuran / 1 h / 0 - 20 °C 3: hydrogenchloride; water / ethanol / Reflux View Scheme

C10H15N3O2S → 4-amino-3-methylbenzenesulfonamide (53297-70-4)

Conditions	Yield
Stage #1: C10H15N3O2S With lithium hydroxide; water In methanol at 50℃; for 5h; Stage #2: With hydrogenchloride In methanol; water at 25℃; for 0.25h; pH=9;

2-aminotoluene-5-sulfonic acid (98-33-9) → 4-amino-3-methylbenzenesulfonamide (53297-70-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: pyridine / 2 h / 20 °C 2.1: sodium hydroxide / pyridine / 3 h / 20 °C 2.2: 2 h / -30 - 40 °C 3.1: ammonium hydroxide / tetrahydrofuran / 1 h / 0 - 20 °C 4.1: hydrogenchloride / ethanol; water / 80 °C View Scheme
Multi-step reaction with 5 steps 1: pyridine / 2 h / 20 °C 2: sodium hydroxide / water / 3 h / 20 °C 3: thionyl chloride / N,N-dimethyl-formamide / 2 h / -40 - 20 °C 4: ammonium hydroxide / water; tetrahydrofuran / 1 h / 0 - 20 °C 5: hydrogenchloride; water / ethanol / Reflux View Scheme

4-acetamido-3-methylbenzenesulfonic acid → 4-amino-3-methylbenzenesulfonamide (53297-70-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / pyridine / 3 h / 20 °C 1.2: 2 h / -30 - 40 °C 2.1: ammonium hydroxide / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: hydrogenchloride / ethanol; water / 80 °C View Scheme
Multi-step reaction with 4 steps 1: sodium hydroxide / water / 3 h / 20 °C 2: thionyl chloride / N,N-dimethyl-formamide / 2 h / -40 - 20 °C 3: ammonium hydroxide / water; tetrahydrofuran / 1 h / 0 - 20 °C 4: hydrogenchloride; water / ethanol / Reflux View Scheme

6-nitro-toluene-3-sulfonic acid amide → 4-amino-3-methylbenzenesulfonamide (53297-70-4)

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol at 20℃;

[4-chloro-3-(3-chloro-5-cyano-phenoxy)-2-fluoro-phenyl]-acetyl chloride (1007571-96-1) + 4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[4-chloro-3-(3-chloro-5-cyano-phenoxy)-2-fluoro-phenyl]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Stage #1: [4-chloro-3-(3-chloro-5-cyano-phenoxy)-2-fluoro-phenyl]-acetyl chloride; 4-amino-3-methylbenzenesulfonamide With sodium hydrogencarbonate In acetone at 20℃; for 24h; Stage #2: With hydrogenchloride In water; acetone at 0℃;	90%

C15H7BrCl2FNO2 (1056598-54-9) + 4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[4-Bromo-3-(3-chloro-5-cyano-phenoxy)-2-fluoro-phenyl]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Stage #1: C15H7BrCl2FNO2; 4-amino-3-methylbenzenesulfonamide With sodium hydrogencarbonate In acetone at 0 - 20℃; for 24h; Stage #2: With hydrogenchloride In water; acetone	87%
Stage #1: C15H7BrCl2FNO2; 4-amino-3-methylbenzenesulfonamide With sodium hydrogencarbonate In acetone at 20℃; for 24h; Stage #2: With hydrogenchloride In water; acetone at 0℃;	87%

4-amino-3-methylbenzenesulfonamide (53297-70-4) + 2-Bromoacetyl bromide (598-21-0) → N-[4-(aminosulfonyl)-2-methylphenyl]-2-bromoacetamide (329944-57-2)

Conditions	Yield
With pyridine In chloroform at 20℃;	69%
With pyridine In chloroform at 0 - 20℃; for 18.3333h;	69%

[2-(3-cyanobenzoyl)-4-(trifluoromethyl)phenoxy]acetyl chloride (329943-23-9) + 4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[2-(3-cyano-benzoyl)-4-trifluoromethyl-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
With sodium hydrogencarbonate In acetone at 20℃; for 2.5h;	53%

3-(2-(3-(5-(2-methyl-1H-imidazol-1-yl)thiophen-2-yl)-3-oxopropyl)-1,3-dioxolan-2-yl)propanoic acid (1338799-46-4) + 4-amino-3-methylbenzenesulfonamide (53297-70-4) → 3-(5-(5-(2-methyl-1H-imidazol-1-yl)thiophen-2-yl)-1-(2-methyl-4-sulfamoylphenyl)-1H-pyrrol-2-yl)propanoic acid (1208317-17-2)

Conditions	Yield
In acetic acid at 120℃;	31%

4-amino-3-methylbenzenesulfonamide (53297-70-4) + 2-((5-bromo-2-chloropyrimidin-4-yl)amino)-6-fluorobenzamide → 2-((5-bromo-2-((2-methyl-4-sulfamoylphenyl)amino)pyrimidin-4-yl)amino)-6-fluorobenzamide

Conditions	Yield
With trifluoroacetic acid In iso-butanol at 100℃; for 16h;	21%

(Z)-9-octadecenoyl chloride (112-77-6) + 4-amino-3-methylbenzenesulfonamide (53297-70-4) → 6-oleoylamino-toluenesulfonamide-(3)

Conditions	Yield
With pyridine

4-amino-3-methylbenzenesulfonamide (53297-70-4) + dibutylamine (111-92-2) + acetyl chloride (75-36-5) → 2-Methyl-benzene-1,4-disulfonic acid 4-(acetyl-amide) 1-dibutylamide

Conditions	Yield
Multistep reaction;

4-amino-3-methylbenzenesulfonamide (53297-70-4) + ({4-chloro-2-[(3-cyanophenyl)carbonyl]phenyl}oxy)acetyl chloride (329944-30-1) → 2-[4-chloro-2-(3-cyano-benzoyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
With sodium hydrogencarbonate In acetone at 20℃;	71.25 g

4-amino-3-methylbenzenesulfonamide (53297-70-4) + [4-chloro-2-(3-fluoro-5-trifluoromethylbenzoyl)phenoxy]acetyl chloride (675139-67-0) → GW4511

Conditions	Yield
With sodium hydrogencarbonate In acetone at 20℃; for 24h;	9 g

[(1-mesityl-1H-tetrazol-5-yl)thio]acetic acid (436095-23-7) + 4-amino-3-methylbenzenesulfonamide (53297-70-4) → N-[4-(aminosulfonyl)-2-methylphenyl]-2-[(1-mesityl-1H-tetrazol-5-yl)thio]acetamide

Conditions	Yield
With phosphorus pentachloride In chloroform; toluene at 20 - 70℃;
With phosphorus pentachloride In chloroform; toluene at 20 - 70℃; for 4.5h;

4-amino-3-methylbenzenesulfonamide (53297-70-4) → N-[4-(aminosulfonyl)-2-methylphenyl]-2-iodoacetamide (329944-70-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 92 percent / N-[4-(aminosulfonyl)-2-methylphenyl]-2-chloroacetamide; NaI / acetone / 20 h / 20 °C View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[2-(3,5-difluoro-benzoyl)-thiophen-3-yloxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 28 percent / K2CO3 / acetone / 6 h / Heating View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[4-chloro-2-(3-chloro-5-methyl-benzoyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Multi-step reaction with 3 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 92 percent / N-[4-(aminosulfonyl)-2-methylphenyl]-2-chloroacetamide; NaI / acetone / 20 h / 20 °C 3: 44 percent / K2CO3 / acetone / 22 h View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[4-chloro-2-(3,5-dimethyl-benzoyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Multi-step reaction with 3 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 92 percent / N-[4-(aminosulfonyl)-2-methylphenyl]-2-chloroacetamide; NaI / acetone / 20 h / 20 °C 3: 44 percent / K2CO3 / acetone / 22 h View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[4-chloro-2-(5-cyano-pyridine-3-carbonyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 3 percent / K2CO3; NaI / acetone / Heating View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[4-chloro-2-(3,5-dimethoxy-benzoyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 37 percent / K2CO3 / acetone / 22 h View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[2-(3-bromo-5-chloro-benzoyl)-4-chloro-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 17 percent / K2CO3 / acetone / 22 h View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[4-chloro-2-(3-cyano-5-methyl-benzoyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 66 percent / K2CO3 / acetone / 22 h View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[2-(3-bromo-5-trifluoromethyl-benzoyl)-4-chloro-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 3 percent / K2CO3; NaI / acetone / Heating View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[4-chloro-2-(3-cyano-5-trifluoromethyl-benzoyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 38 percent / K2CO3 / acetone / 22 h View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) → N-[4-(aminosulfonyl)-2-methylphenyl]-2-[4-chloro-2-(3-chloro-5-cyanobenzoyl)phenoxy]acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 12 percent / K2CO3 / acetone / 22 h View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) + chloroacetyl chloride (79-04-9) → N-[4-(aminosulfonyl)-2-methylphenyl]-2-chloroacetamide (53297-88-4)

6-chloropyrimidine-4-carbonyl chloride (263270-52-6) + 4-amino-3-methylbenzenesulfonamide (53297-70-4) → 6-chloro-pyrimidine-4-carboxylic acid (2-methyl-4-sulfamoyl-phenyl)-amide (1114592-11-8)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;
With N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0℃; for 0.5h;

2-chloro-9-cyclopentyl-7-methyl-7H-purin-8(9H)-one (1124329-94-7) + 4-amino-3-methylbenzenesulfonamide (53297-70-4) → 4-[(9-cyclopentyl-7-methyl-8-oxo-8,9-dihydro-7H-purin-2-yl)-amino]-3-methylbenzenesulfonamide (1124329-10-7)

Conditions	Yield
Stage #1: 2-chloro-9-cyclopentyl-7-methyl-7H-purin-8(9H)-one; 4-amino-3-methylbenzenesulfonamide With toluene-4-sulfonic acid In Methyl isobutyl carbinol at 200℃; for 0.0833333h; Microwave irradiation; Stage #2: With SCX column; ammonia In methanol; Methyl isobutyl carbinol Product distribution / selectivity;
Stage #1: 2-chloro-9-cyclopentyl-7-methyl-7H-purin-8(9H)-one; 4-amino-3-methylbenzenesulfonamide With toluene-4-sulfonic acid In butan-1-ol at 200℃; for 0.0833333h; Microwave irradiation; Stage #2: With SCX column; ammonia In methanol; butan-1-ol Product distribution / selectivity;

7-methoxy-2-oxo-8-propyl-2H-chromene-3-carboxylic acid (952504-50-6) + 4-amino-3-methylbenzenesulfonamide (53297-70-4) → N-[4-(aminosulfonyl)-2-methylphenyl]-7-methoxy-2-oxo-8-propyl-2H-chromene-3-carboxamide (1296198-11-2)

Conditions	Yield
Stage #1: 7-methoxy-2-oxo-8-propyl-2H-chromene-3-carboxylic acid With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate at 20℃; for 0.5h; Stage #2: 4-amino-3-methylbenzenesulfonamide In dichloromethane; ethyl acetate at 20℃;

Upstream product

• 98-33-9 2-aminotoluene-5-sulfonic acid 
• 14988-21-7 4-(acetylamino)-3-methylbenzenesulfonyl chloride 
• 252562-03-1 N-[4-(aminosulfonyl)-2-methylphenyl]acetamide 

Downstream Products

• 1234481-10-7 XMD-12-3-1 
• 1341199-23-2 N-[4-(aminosulfonyl)-2-methylphenyl]-2-(4-chloro-2-nitrophenoxy)acetamide 
• 1416364-06-1 C₂₆H₂₂ClN₃O₅S 
• 1416364-05-0 C₂₆H₂₂ClN₃O₅S 
• 1416364-04-9 C₂₃H₂₀Cl₃N₃O₅S 
• 1416364-03-8 C₂₄H₂₂ClN₃O₅S 
• 1416364-02-7 C₂₃H₁₈Cl₂N₄O₅S 
• 1416364-01-6 C₂₂H₁₈Br₂ClN₃O₅S 
• 1416364-00-5 C₂₂H₁₈BrCl₂N₃O₅S 
• 1416363-99-9 C₂₂H₁₈Cl₃N₃O₅S 

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