6973-09-7

Basic information

• Product Name: 3-Amino-6-methylbenzenesulfonamide
• Synonyms: methyl 2,4-difluoro-5-nitrobenzoate;Nsc36969;5-aMino-2-Methylbenzene-1-sulfonaMide;2-Methyl-5-AMiobenzenesulfonMide;3-Amino-6-methylbenzenesulfonamide 5-Amino-2-methylbenzenesulfonamide;6973/9/7;2-METHYL-5-AMINOBENZENE SULFONAMIDE;3-Amino-6-methylbenzenesulfonamide
• CAS NO: 6973-09-7
• Molecular Formula: C₇H₁₀N₂O₂S
• Molecular Weight: 186.23
• EINECS: 1592732-453-0
• Product Categories: Amides;Amines;Building Blocks;C2 to C7;C7;Carbonyl Compounds;Chemical Synthesis;New Products for Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Sulfonamides/Sulfinamides;Sulfur Compounds;SULFONAMIDE;Nitro / Nitriles
• Mol File: 6973-09-7.mol
• Article Data: 15

Chemical Properties

• Melting Point: 163-164℃
• Boiling Point: 421.5 °C at 760 mmHg
• Flash Point: 208.7 °C
• Appearance: /
• Density: 1.359 g/cm³
• Vapor Pressure: 2.6E-07mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 10.43±0.60(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 3-Amino-6-methylbenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-6-methylbenzenesulfonamide(6973-09-7)
• EPA Substance Registry System: 3-Amino-6-methylbenzenesulfonamide(6973-09-7)

Safety Data

• Hazardous Substances Data: 6973-09-7(Hazardous Substances Data)

Usage

Description

3-Amino-6-methylbenzenesulfonamide is an organic compound that serves as a key intermediate in the synthesis of various pharmaceuticals and chemical compounds. It is characterized by the presence of an amino group attached to a benzene ring, with a methyl group and a sulfonamide group also attached to the ring. This unique structure endows it with versatile reactivity and potential applications in different industries.

Uses

Used in Pharmaceutical Industry:
3-Amino-6-methylbenzenesulfonamide is used as an intermediate in the synthesis of Pazopanib (P210925), an oral angiogenesis inhibitor that targets VEGFR and PDGFR. 3-Amino-6-methylbenzenesulfonamide plays a crucial role in the development of drugs that can effectively inhibit the formation of new blood vessels in tumors, thereby restricting their growth and spread.
In the synthesis of Pazopanib, 3-Amino-6-methylbenzenesulfonamide serves as a building block, contributing to the formation of the final drug molecule. Its presence in the synthesis process is essential for achieving the desired pharmacological properties and therapeutic effects of Pazopanib.
Furthermore, due to its reactivity and structural features, 3-Amino-6-methylbenzenesulfonamide may also be used as a starting material or intermediate in the synthesis of other pharmaceuticals and chemical compounds with various applications. Its versatility in chemical reactions allows it to be a valuable component in the development of new drugs and materials in the pharmaceutical and chemical industries.

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

Synthetic route

4-acetylamino-toluene-2-sulfonic acid amide (200266-64-4) → 5-amino-2-methylbenzenesulfonamide (6973-09-7)

Conditions	Yield
With hydrogenchloride for 0.333333h; Heating;	75%
With hydrogenchloride

4-nitro-toluene-sulfonic acid-(2)-amide → 5-amino-2-methylbenzenesulfonamide (6973-09-7)

Conditions	Yield
With ammonium sulfide

4-Methylacetanilide (103-89-9) → 5-amino-2-methylbenzenesulfonamide (6973-09-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 67 percent / conc. aq. NH4OH 2: 75 percent / 18percent aq. HCl / 0.33 h / Heating View Scheme

4-nitrotoluene-2-sulfonamide (6269-91-6) → 5-amino-2-methylbenzenesulfonamide (6973-09-7)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride In diethylene glycol dimethyl ether; water for 0.75h;
With hydrogen; palladium 10% on activated carbon In methanol; dichloromethane under 2585.81 Torr; for 0.25h;
palladium-carbon In methanol; dichloromethane

1-methyl-4-nitrobenzene (99-99-0) → 5-amino-2-methylbenzenesulfonamide (6973-09-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: chlorosulfonic acid / 24 h / 0 - 110 °C 2: ammonium hydroxide / water; ethyl acetate / 20 °C 3: palladium 10% on activated carbon; hydrogen / methanol; dichloromethane / 0.25 h / 2585.81 Torr View Scheme
Multi-step reaction with 2 steps 1.1: chlorosulfonic acid / 24 h / 0 - 110 °C 1.2: 20 °C 2.1: palladium 10% on activated carbon; hydrogen / methanol; dichloromethane / 0.25 h / 2585.81 Torr View Scheme
Multi-step reaction with 3 steps 1: chlorosulfonic acid / 24 h / 0 - 110 °C 2: ammonium hydroxide / ethyl acetate / 20 °C 3: palladium 10% on activated carbon; hydrogen / methanol; dichloromethane / 0.25 h / 2585.81 Torr View Scheme
Multi-step reaction with 2 steps 1: chlorosulfonic acid / 24 h / 0 - 110 °C 2: palladium 10% on activated carbon; hydrogen / methanol; dichloromethane / 0.25 h / 2585.81 Torr View Scheme

2-methyl-5-nitrobenzene-1-sulfonyl chloride (121-02-8) → 5-amino-2-methylbenzenesulfonamide (6973-09-7)

Conditions	Yield
With palladium on activated charcoal In tetrahydrofuran at 100℃; for 8h; Temperature; Solvent; Reagent/catalyst;
Multi-step reaction with 2 steps 1: ammonium hydroxide / ethyl acetate / 20 °C 2: palladium 10% on activated carbon; hydrogen / methanol; dichloromethane / 0.25 h / 2585.81 Torr View Scheme

5-amino-2-methylbenzenesulfonamide (6973-09-7) + 4-nitrobenzaldehdye (555-16-8) → 5-(p-Nitrobenzylideneamino)-2-toluenesulfonamide

Conditions	Yield
In N,N-dimethyl-formamide for 0.0166667h; Irradiation;	98%

2,3-dimethyl-N-(2-chloropyrimidin-4-yl)-N-methyl-2H-indazole-6-amine (444731-75-3) + 5-amino-2-methylbenzenesulfonamide (6973-09-7) → pazopanib hydrochloride

Conditions	Yield
With hydrogenchloride In isopropyl alcohol Reflux;	97%
Stage #1: N-(2-chloropyrimidin-4-yl)-N-methyl-2,3-dimethyl-2H-indazole-6-amine; 5-amino-2-methylbenzenesulfonamide In ethanol at 68 - 72℃; for 3h; Stage #2: With hydrogenchloride In 1,4-dioxane; ethanol at 68 - 72℃; for 0.0333333h; Product distribution / selectivity;	96.4%
Stage #1: N-(2-chloropyrimidin-4-yl)-N-methyl-2,3-dimethyl-2H-indazole-6-amine; 5-amino-2-methylbenzenesulfonamide In ethanol at 68 - 72℃; for 3h; Heating / reflux; Stage #2: With hydrogenchloride In 1,4-dioxane; ethanol at 68 - 72℃; for 8h;	96.4%

5-nitrofurane-2-carboxaldehyde (698-63-5) + 5-amino-2-methylbenzenesulfonamide (6973-09-7) → 5-(5'-Nitro-2'-furfurylideneamino)-2-toluenesulfonamide

Conditions	Yield
In N,N-dimethyl-formamide for 0.0333333h; Irradiation;	96%

5-(4-nitrophenyl)-2-furaldehyde (7147-77-5) + 5-amino-2-methylbenzenesulfonamide (6973-09-7) → 5-[5'-(p-Nitrophenyl)-2'-furfurylideneamino]-2-toluenesulfonamide

Conditions	Yield
In N,N-dimethyl-formamide for 0.0333333h; Irradiation;	96%

N-(2-chloropyrimidin-4-yl)-2,3-dimethyl-2H-indazol-6-amine (444731-74-2) + 5-amino-2-methylbenzenesulfonamide (6973-09-7) → 5-[4-[(2,3-dimethyl-2H-indazol)-6-ylamino]pyrimidin-2-ylamino]-2-methylbenzenesulfonamide hydrochloride

Conditions	Yield
With hydrogenchloride In methanol; ethyl acetate for 3h; Reflux;	96%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 5-amino-2-methylbenzenesulfonamide (6973-09-7) → 5-(5'-Nitro-2'-thienylmethylideneamino)-2-toluenesulfonamide

Conditions	Yield
In N,N-dimethyl-formamide for 0.0166667h; Irradiation;	92%

8-quinolinol (148-24-3) + 5-amino-2-methylbenzenesulfonamide (6973-09-7) → (E)-5-((8-hydroxyquinolin-5-yl)diazenyl)-2-methylbenzenesulfonamide

Conditions	Yield
Stage #1: 5-amino-2-methylbenzenesulfonamide With hydrogenchloride; sodium nitrite In water at -5℃; for 0.25h; Stage #2: 8-quinolinol With sodium hydroxide In water	92%

5-amino-2-methylbenzenesulfonamide (6973-09-7) + 2-chloro-benzaldehyde (89-98-5) → 5-(o-Chlorobenzylideneamino)-2-toluenesulfonamide

Conditions	Yield
In N,N-dimethyl-formamide for 0.0333333h; Irradiation;	90%

2,3-dimethyl-N-(2-chloropyrimidin-4-yl)-N-methyl-2H-indazole-6-amine (444731-75-3) + 5-amino-2-methylbenzenesulfonamide (6973-09-7) → pazopanib

Conditions	Yield
With hydrogenchloride In water; isopropyl alcohol at 85℃;	90%

5-amino-2-methylbenzenesulfonamide (6973-09-7) + C14H13ClN6O2 → C21H22N8O4S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In methanol at 60℃;	87%

5-amino-2-methylbenzenesulfonamide (6973-09-7) + 4-chloro-benzoyl chloride (122-01-0) → 5-(p-Chlorobenzoylamino)-2-toluenesulfonamide

Conditions	Yield
In 1,4-dioxane for 1h; Ambient temperature;	85%

5-amino-2-methylbenzenesulfonamide (6973-09-7) + 4-nitro-benzoyl chloride (122-04-3) → 5-(p-Nitrobenzoylamino)-2-toluenesulfonamide

Conditions	Yield
In 1,4-dioxane for 0.5h; Ambient temperature;	85%

5-amino-2-methylbenzenesulfonamide (6973-09-7) + 1-hydroxy-2-naphthoic acid (86-48-6) → (E)-1-hydroxy-4-((4-methyl-3-sulfamoylphenyl)diazenyl)-2-naphthoic acid

Conditions	Yield
Stage #1: 5-amino-2-methylbenzenesulfonamide With hydrogenchloride; sodium nitrite In water at -5℃; for 0.25h; Stage #2: 1-hydroxy-2-naphthoic acid With sodium hydroxide In water	85%

5-amino-2-methylbenzenesulfonamide (6973-09-7) + 2-hydroxy-1-naphthalenecarboxylic acid (2283-08-1) → (E)-2-hydroxy-3-((4-methyl-3-sulfamoylphenyl)diazenyl)-1-naphthoic acid

Conditions	Yield
Stage #1: 5-amino-2-methylbenzenesulfonamide With hydrogenchloride; sodium nitrite In water at -5℃; for 0.25h; Stage #2: 2-hydroxy-1-naphthalenecarboxylic acid With sodium hydroxide In water	81%

2-furancarbonyl chloride (527-69-5) + 5-amino-2-methylbenzenesulfonamide (6973-09-7) → Furan-2-carboxylic acid (4-methyl-3-sulfamoyl-phenyl)-amide

Conditions	Yield
In 1,4-dioxane for 1h; Ambient temperature;	80%

5-amino-2-methylbenzenesulfonamide (6973-09-7) + benzyl alcohol (100-51-6) → 5-amino-N-benzyl-2-methylbenzenesulfonamide

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; caesium carbonate In tert-Amyl alcohol at 120℃; for 12h; Inert atmosphere; Schlenk technique;	79%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; caesium carbonate In tert-Amyl alcohol at 120℃; for 12h; Inert atmosphere; Schlenk technique;	79%

5-amino-2-methylbenzenesulfonamide (6973-09-7) + C9H8ClFN4S → C16H17FN6O2S2

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In tetrahydrofuran at 35 - 55℃; Buchwald-Hartwig Coupling; Inert atmosphere;	79%

(2-chloropyrimidin-4-yl)-(1,3-dimethyl-1H-indazol-6-yl)-methylamine (1042366-93-7) + 5-amino-2-methylbenzenesulfonamide (6973-09-7) → 5-(4-[(1,3-dimethyl-1H-indazol-6-yl)methylamino]-pyrimidin-2-ylamino)-2-methylbenzenesulfonamide hydrochloride

Conditions	Yield
With hydrogenchloride In water; isopropyl alcohol for 18h; Reflux;	79%

8-amino-2-naphthol (118-46-7) + 5-amino-2-methylbenzenesulfonamide (6973-09-7) → (E)-5-((4-amino-6-hydroxynaphthalen-1-yl)diazenyl)-2-methylbenzenesulfonamide

Conditions	Yield
Stage #1: 5-amino-2-methylbenzenesulfonamide With hydrogenchloride; sodium nitrite In water at -5℃; for 0.25h; Stage #2: 8-amino-2-naphthol With sodium acetate In water	79%

5-amino-1-naphthol (83-55-6) + 5-amino-2-methylbenzenesulfonamide (6973-09-7) → (E)-5-((4-amino-8-hydroxynaphthalen-1-yl)diazenyl)-2-methylbenzenesulfonamide

Conditions	Yield
Stage #1: 5-amino-2-methylbenzenesulfonamide With hydrogenchloride; sodium nitrite In water at -5℃; for 0.25h; Stage #2: 5-amino-1-naphthol With sodium acetate In water	79%

7-hydroxy-2H-chromen-2-one (93-35-6) + 5-amino-2-methylbenzenesulfonamide (6973-09-7) → (E)-5-((7-hydroxy-2-oxo-2H-chromen-6-yl)diazenyl)-2-methylbenzenesulfonamide

Conditions	Yield
Stage #1: 5-amino-2-methylbenzenesulfonamide With hydrogenchloride; sodium nitrite In water at -5℃; for 0.25h; Stage #2: 7-hydroxy-2H-chromen-2-one With sodium hydroxide In water	79%

5-amino-2-methylbenzenesulfonamide (6973-09-7) + 2-chloro-4-(4-(2-(2-pyridinyl)ethenyl)phenoxy)pyrimidine → N-(4-methyl-3-sulfamoylphenyl)-4-(4-(2-(2-pyridinyl)ethenyl)phenoxy)pyrimidin-2-amine

Conditions	Yield
With hydrogenchloride In water; isopropyl alcohol for 4h; Reflux;	78%

5-bromofuran-2-carbonyl chloride (26726-16-9) + 5-amino-2-methylbenzenesulfonamide (6973-09-7) → 5-Bromo-furan-2-carboxylic acid (4-methyl-3-sulfamoyl-phenyl)-amide

Conditions	Yield
In 1,4-dioxane for 0.5h; Ambient temperature;	75%

5-amino-2-methylbenzenesulfonamide (6973-09-7) + 6-(2-chloropyrimidin-4-ylamino)-4-methyl-4H-benzo[1,4]oxazin-3-one → C20H20N6O4S

Conditions	Yield
With hydrogenchloride In ethanol; water at 65 - 70℃; for 4h; pH=5 - 6;	75%

5-amino-2-methylbenzenesulfonamide (6973-09-7) + C15H15N3OS → 2-methyl-5-((3-(3-methylbenzo[4,5]imidazo[2,1-b]thiazol-2-yl)-3-oxoprop-1-en-1-yl)amino)benzenesulfonamide

Conditions	Yield
With acetic acid for 5h; Reflux;	74%

5-amino-2-methylbenzenesulfonamide (6973-09-7) + C10H7NO2 → 3-(3-methyl-1-benzofuran-2-yl)-1-(4-methyl-3-sulfamoylphenyl)urea

Conditions	Yield
In toluene for 6h; Reflux;	73%

furfural (98-01-1) + 5-amino-2-methylbenzenesulfonamide (6973-09-7) → 5-(2'-Furfurylideneamino)-2-toluenesulfonamide

Conditions	Yield
In N,N-dimethyl-formamide for 0.0333333h; Irradiation;	72%

5-amino-2-methylbenzenesulfonamide (6973-09-7) + 5-bromo-2-isocyanatobenzofuran → 3-(5-bromo-1-benzofuran-2-yl)-1-(4-methyl-3-sulfamoylphenyl)urea

Conditions	Yield
In toluene for 6h; Reflux;	71%

Upstream product

• 121-02-8 2-methyl-5-nitrobenzene-1-sulfonyl chloride 
• 99-99-0 1-methyl-4-nitrobenzene 
• 6269-91-6 4-nitrotoluene-2-sulfonamide 
• 103-89-9 4-Methylacetanilide 
• 200266-64-4 4-acetylamino-toluene-2-sulfonic acid amide 

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