CAS 80-20-6

3-Amino-4-hydroxy-N-phenylbenzenesulfonamide

Description:

3-Amino-4-hydroxy-N-phenylbenzenesulfonamide, commonly known as sulfanilamide, is an organic compound that belongs to the sulfonamide class of antibiotics. It features a sulfonamide functional group, which is characterized by the presence of a sulfonyl group (–SO2) attached to an amine. This compound is typically a white to off-white crystalline solid that is soluble in water and exhibits moderate stability under standard conditions. Its structure includes an amino group (–NH2) and a hydroxy group (–OH), which contribute to its biological activity. Sulfanilamide acts as a competitive inhibitor of the bacterial enzyme dihydropteroate synthase, thereby interfering with folate synthesis in bacteria, making it effective against certain bacterial infections. Additionally, it has applications in various fields, including pharmaceuticals and biochemistry. However, its use has declined with the advent of more effective antibiotics, and it is primarily of historical significance in the development of antimicrobial therapies. Safety precautions should be observed when handling this compound, as it may cause allergic reactions in sensitive individuals.

Formula: C₁₂H₁₂N₂O₃S

InChI: InChI=1S/C12H12N2O3S/c13-11-8-10(6-7-12(11)15)18(16,17)14-9-4-2-1-3-5-9/h1-8,14-15H,13H2

InChI key: InChIKey=IAOZVUUQCPRLOI-UHFFFAOYSA-N

SMILES: S(NC1=CC=CC=C1)(=O)(=O)C2=CC(N)=C(O)C=C2

Synonyms:

• 1-Phenol-4-sulfonanilide, 2-amino-
• 3-Amino-4-Hydroxybenzenesulfonamide
• 3-Amino-4-hydroxy-N-phenylbenzene-1-sulfonamide
• 3-Amino-4-hydroxy-N-phenylbenzenesulphonamide
• 3-Amino-4-hydroxybenzenesulfonanilide
• 3-amino-4-hydroxy-N-phenylbenzenesulfonamide
• 4-Hydroxymetanilanilide
• Ai3-62996
• Benzenesulfonamide, 3-amino-4-hydroxy-N-phenyl-
• Metanilanilide, 4-hydroxy-
• Metanilanilide, 4-hydroxy- (8CI)

3-Amino-4-hydroxy-N-phenylbenzenesulfonamide

CAS: 80-20-6

Formula: C₁₂H₁₂N₂O₃S

Molecular weight: 264.3003

Ref: IN-DA00G2CA