3-Amino-6-methylbenzenesulfonamide
[CAS# 6973-09-7]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: 3-Amino-6-methylbenzenesulfonamide
• Synonyms: 5-Amino-2-methylbenzenesulfonamide
• Molecular Formula: C₇H₁₀N₂O₂S
• Molecular Weight: 186.23
• CAS Registry Number: 6973-09-7
• EC Number: 691-180-5
• SMILES: CC1=C(C=C(C=C1)N)S(=O)(=O)N

Properties

• Melting point: 163-164 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

3-Amino-6-methylbenzenesulfonamide, commonly known as aromatic sulfonamide, is a compound consisting of an amino and sulfonamide group on a benzene ring combined with a methyl substituent. The compound was first synthesized in the early 20th century as part of the research on sulfonamides, which are known for their antibacterial properties. Researchers explored different modification methods to improve the efficacy and selectivity of sulfonamides. The introduction of amino and methyl groups into the benzenesulfonamide core resulted in 3-amino-6-methylbenzenesulfonamide. Its discovery has been important in advancing the understanding of sulfonamide chemistry and its applications.

3-Amino-6-methylbenzenesulfonamide has been studied for its potential therapeutic applications. Sulfonamides are known for their antibacterial properties. Modifications in this compound affect its activity and selectivity and can serve as a lead compound for the development of new antibiotics or as a scaffold for drug design to treat bacterial infections.

In diagnostic chemistry, 3-amino-6-methylbenzenesulfonamide is used as a reagent in assays and tests. Its chemical properties allow it to interact with a variety of biological and chemical substances and can be used to develop diagnostic tools and assays for the detection of specific conditions or compounds.

This compound is used to study the behavior and interactions of sulfonamide derivatives. Its structure provides insights into the structure-activity relationship of sulfonamides, which can help develop more effective drugs and understand their mechanisms of action.

In organic chemistry, 3-amino-6-methylbenzenesulfonamide is a building block for the synthesis of other complex molecules. Its functional groups allow chemists to modify and expand its structure, making it a valuable ingredient for creating a variety of organic compounds.

References

2022. A patent review on efficient strategies for the total synthesis of pazopanib, regorafenib and lenvatinib as novel anti-angiogenesis receptor tyrosine kinase inhibitors for cancer therapy. Molecular Diversity, 26(5).
DOI: 10.1007/s11030-022-10406-8

2009. 5-Amino-2-methyl-benzene-sulfonamide. Acta crystallographica. Section E, Structure reports online, 65(8).
DOI: 10.1107/s1600536809026142