137-65-5

Basic information

• Product Name: 2-Aminobenzoic acid-5-sulfonamide
• Synonyms: 2-AMINO BENZOIC ACID-5-SULFONAMIDE;2-AMINO-5-SULFAMOYLBENZOIC ACID;2-amino-5-(aminosulphonyl)benzoic acid;5-Sulfamoylanthranilic acid (COOH=1);2-Amino Benzoic Acid-5-Sulfonamide 2-Amino-5-Sulfonamide Benzoic Acid;1-Amino-2-carboxybenzene-4-sulfonamide;ABAS;2-Amino-5-SulfonamideBenzoicAcid
• CAS NO: 137-65-5
• Molecular Formula: C₇H₈N₂O₄S
• Molecular Weight: 216.21
• EINECS: 205-304-9
• Mol File: 137-65-5.mol
• Article Data: 1

Chemical Properties

• Melting Point: 246 °C (decomp)
• Boiling Point: 518.744 °C at 760 mmHg
• Flash Point: 267.527 °C
• Appearance: white crystal
• Density: 1.623 g/cm³
• Vapor Pressure: 1.38E-11mmHg at 25°C
• Refractive Index: 1.658
• PKA: 4.41±0.10(Predicted)
• CAS DataBase Reference: 2-Aminobenzoic acid-5-sulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Aminobenzoic acid-5-sulfonamide(137-65-5)
• EPA Substance Registry System: 2-Aminobenzoic acid-5-sulfonamide(137-65-5)

Safety Data

• Hazardous Substances Data: 137-65-5(Hazardous Substances Data)

Usage

General Description

2-Aminobenzoic acid-5-sulfonamide, also known as sulfanilamide, is an organic compound that belongs to the sulfonamide class of antibiotics. It is composed of a benzene ring with a sulfonamide group and an amino group attached to it. Sulfanilamide is commonly used as an antimicrobial agent and has been historically used in the treatment of various bacterial infections. It works by interfering with the synthesis of folic acid in bacteria, thereby inhibiting their growth and proliferation. Sulfanilamide has also been used in the treatment of urinary tract infections, burn wounds, and other bacterial infections. Additionally, it has found other uses in the pharmaceutical industry as a starting material for the synthesis of other drugs and as a component in dyes and chemical reactions.

InChI:InChI=1/C7H8N2O4S/c8-6-2-1-4(14(9,12)13)3-5(6)7(10)11/h1-3H,8H2,(H,10,11)(H2,9,12,13)

Synthetic route

2-acetylamino-5-sulfamoyl-benzoic acid → 2-amino-5-sulfamoylbenzoic acid (137-65-5)

Conditions	Yield
With hydrogenchloride

2-hydroxyoxalylamino-5-sulfamoyl-benzoic acid → 2-amino-5-sulfamoylbenzoic acid (137-65-5)

Conditions	Yield
With sodium hydroxide

methanol (67-56-1) + 4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid (54-31-9) → 2-furfurylamino-5-sulfamoyl-benzoic acid (4818-85-3) + 2-amino-5-sulfamoylbenzoic acid (137-65-5) + 4-chloro-5-sulfamoylanthranilic acid (3086-91-7) + 2-Amino-4-methoxy-5-sulfamoyl-benzoic acid + 2-[(Furan-2-ylmethyl)-amino]-4-methoxy-5-sulfamoyl-benzoic acid

Conditions	Yield
at 30℃; for 0.166667h; Mechanism; Quantum yield; Irradiation;

N-[4-(aminosulfonyl)-2-methylphenyl]acetamide (252562-03-1) → 2-amino-5-sulfamoylbenzoic acid (137-65-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous KMnO4 2: aqueous HCl View Scheme

Upstream product

• 67-56-1 methanol 
• 54-31-9 4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid 
• 252562-03-1 N-[4-(aminosulfonyl)-2-methylphenyl]acetamide 

Relevant articles and documents

Photolytic degradation of frusemide

Irradiation with 365 nm u.v. light of frusemide (4-chloro-N-furfuryl-5-sulphamoyl-anthranilic acid) in methanol results primarily in photoreduction to N-furfuryl-5-sulphamoylanthranilic acid and photohydrolysis to 4-chloro-5-sulphamoylanthranilic acid (saluamine).