6336-70-5

Basic information

• Product Name: 4-sulphanilamidobenzoic acid
• Synonyms: 4-sulphanilamidobenzoic acid;4-(4-Aminophenylsulfonylamino)benzoic acid;4-[(4-Aminophenyl)sulfonylamino]benzoic acid;4-[[(4-Aminophenyl)sulfonyl]amino]benzoic acid;4-Sulfanilamidobenzoic acid
• CAS NO: 6336-70-5
• Molecular Formula: C₁₃H₁₂N₂O₄S
• Molecular Weight: 292.31038
• EINECS: 228-720-2
• Mol File: 6336-70-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 550.2°C at 760 mmHg
• Flash Point: 286.6°C
• Appearance: /
• Density: 1.511g/cm³
• Vapor Pressure: 6.11E-13mmHg at 25°C
• Refractive Index: 1.689
• CAS DataBase Reference: 4-sulphanilamidobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-sulphanilamidobenzoic acid(6336-70-5)
• EPA Substance Registry System: 4-sulphanilamidobenzoic acid(6336-70-5)

Safety Data

• Hazardous Substances Data: 6336-70-5(Hazardous Substances Data)

Usage

Definition

ChEBI: A sulfonamide that is sulfanilamide substituted at the sulfonamide nitrogen by a 4-carboxyphenyl group.

InChI:InChI=1/C13H12N2O4S/c14-10-3-7-12(8-4-10)20(18,19)15-11-5-1-9(2-6-11)13(16)17/h1-8,15H,14H2,(H,16,17)

Upstream product

• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 618-94-0 3-nitrobenzoic acid hydrazide 
• 4291-13-8 2-(4-nitrophenyl)-1,3,4-oxadiazole 
• 5565-72-0 2-(3-nitrobenzene)-1,3,4-oxadiazole 
• 35219-13-7 4-(1,3,4-oxadiazol-2-yl)aniline 
• 150-13-0 4-amino-benzoic acid 
• 1071691-56-9 4-acetylamino-N-(4-[1,3,4]oxadiazol-2-yl-phenyl)-benzenesulfonamide 
• 72236-24-9 4-(4-acetamidophenylsulfonamido)benzoic acid 
• 126145-99-1 4-((4-bromophenyl)sulfonamido)benzoic acid 
• 19837-91-3 4-acetylamino-N-(4-methylphenyl)benzenesulfonamide 

Downstream Products

• 1387556-05-9 4-(4-(sulfamoylamino)phenylsulfonamido)-benzoic acid 
• 873973-86-5 3-[(N-acetyl-sulfanilyl)-amino]-benzoic acid amide 
• 408539-48-0 4-sulfanilylamino-benzoic acid amide 
• 84907-43-7 4-[4-(1,4-Dioxo-1,4-dihydro-naphthalen-2-ylamino)-benzenesulfonylamino]-benzoic acid 
• 126146-00-7 4-(4-iodo-benzenesulfonylamino)-benzoic acid 

Relevant articles and documents

Development of potent carbonic anhydrase inhibitors incorporating both sulfonamide and sulfamide groups

A series of compounds incorporating both sulfonamide and sulfamide as zinc-binding groups (ZBGs) are reported as inhibitors of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). Crystallographic studies on the complex of hCA II with the lead compound of this series, namely, 4-sulfamido- benzenesulfonamide, revealed the binding of two molecules in the enzyme active site cavity, the first one canonically coordinated to the zinc ion by means of the sulfonamide group and the second one located at the entrance of the cavity. This observation led to the design of elongated molecules incorporating these two ZBGs, separated by a linker of proper length, to allow the simultaneous binding to these different sites. The long inhibitors indeed showed around 10 times better enzyme inhibitory properties as compared to the shorter molecules against four physiologically relevant human (h) isoforms, hCA I, II, IX, and XII.

Synthesis of sulfanilamido-naphthoquinones as potential antituberculous agents

p-Aminobenzoic acid, the acid hydrazides of benzoic acid, salicylic acid and isonicotinic acid, and 4,4'-diaminodiphenyl sulfone were condensed with p-aminobenzenesulfonyl chloride to give the corresponding N1-substituted sulfanilamides. These molecules were then treated with 1,4-naphthoquinone to yield 2-substituted-1,4-naphthoquinones. The partition coefficient for the substituted quinones showed, in some cases, high diffusion rates to the organic phase, benzene, from physiological Tyrode's solution. These compounds are effective in low concentration in dioxane against the human sensitive strain of Mycobacterium tuberculosis H37 Rv. Sulfanilamides obtained from p-aminosalicylic acid and thiosemicarbazide failed to react with 1,4-naphthoquinone. These sulfanilamides also showed high activity against the same Mycobacterium.