7151-76-0

Basic information

• Product Name: 4-(METHANESULFONYLAMINO)BENZOIC ACID
• Synonyms: RARECHEM AL BO 0801;P-(METHANESULFONAMIDO)BENZOIC ACID;4-[(METHYLSULFONYL)AMINO]BENZOIC ACID;4-(METHANESULFONYLAMINO)BENZOIC ACID;4-(Methanesulfonylamino)benzoic acid, min. 95 %;p-(Methanesulfonamide)benzoic Acid;4-(Methylsulphonamido)benzoic acid, N-(4-Carboxyphenyl)methanesulphonamide;4MB
• CAS NO: 7151-76-0
• Molecular Formula: C₈H₉NO₄S
• Molecular Weight: 215.23
• Mol File: 7151-76-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 408.8°C at 760 mmHg
• Flash Point: 201°C
• Appearance: /
• Density: 1.51g/cm³
• Vapor Pressure: 2.04E-07mmHg at 25°C
• Refractive Index: 1.621
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.17±0.10(Predicted)
• CAS DataBase Reference: 4-(METHANESULFONYLAMINO)BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(METHANESULFONYLAMINO)BENZOIC ACID(7151-76-0)
• EPA Substance Registry System: 4-(METHANESULFONYLAMINO)BENZOIC ACID(7151-76-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 7151-76-0(Hazardous Substances Data)

Usage

Description

4-(Methanesulfonylamino)benzoic acid, a chemical compound with the formula C8H9NO4S, is a white crystalline solid. It features an aromatic benzene ring with a carboxylic acid functional group and a sulfonamide group. 4-(METHANESULFONYLAMINO)BENZOIC ACID is recognized for its potent inhibitory effect on carbonic anhydrase, making it a significant pharmaceutical intermediate in the synthesis of various compounds and a valuable research tool in drug development.

Uses

Used in Pharmaceutical Industry:
4-(Methanesulfonylamino)benzoic acid is used as a pharmaceutical intermediate for the synthesis of other compounds, leveraging its structural properties to create new therapeutic agents.
Used in Carbonic Anhydrase Inhibition:
4-(Methanesulfonylamino)benzoic acid is used as an inhibitor of carbonic anhydrase for its potential therapeutic applications, particularly in the treatment of conditions such as glaucoma, where the inhibition of this enzyme can help reduce intraocular pressure.
Used in Drug Development Research:
As a research tool, 4-(Methanesulfonylamino)benzoic acid aids in the development of new pharmaceuticals by providing insights into the structure-activity relationships of carbonic anhydrase inhibitors and other related compounds.

InChI:InChI=1/C8H9NO4S/c1-14(12,13)9-7-4-2-6(3-5-7)8(10)11/h2-5,9H,1H3,(H,10,11)

Upstream product

• 619-45-4 4-methoxycarbonyl aniline 
• 7143-01-3 Methanesulfonic anhydride 
• 7151-77-1 ethyl 4-(methylsulfonamido)benzoate 
• 124-63-0 methanesulfonyl chloride 
• 94-09-7 p-aminoethylbenzoate 
• 150-13-0 4-amino-benzoic acid 
• 50790-28-8 methyl 4-(methanesulfonylamino)benzoate 

Downstream Products

• 1429226-60-7 C₁₇H₁₇N₃O₅S₂ 
• 1333426-76-8 N-{(S)-[1-(1-cyano-cyclopropyl)-1H-[1,2,3]triazol-4-yl]-cyclohexyl-methyl}-4-methanesulfonylamino-benzamide 
• 1357294-90-6 N-[4-(6,7-dimethoxy-3-n-butyl-4-oxo-3,4-dihydroquinazolin-2-yl)phenyl]methanesulfonamide 
• 1357294-65-5 4,5-dimethoxy-N-n-butyl-2-{[4-((methylsulfonyl)amino)phenyl]carboxamido}benzamide 
• 1218934-92-9 (R)-N-(6-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)imidazo[1,2-b]pyridazin-3-yl)-4-(methylsulfonamido)benzamide 

Relevant articles and documents

Convenient synthesis of primary sulfonamides

An efficient protocol for a one-pot synthesis of mono-sulfonamides has been developed. It features utilization of excess of sulfonylating agent followed by base mediated recovery of the primary sulfonamide.

Compounds useful as reversible inhibitors of cysteine proteases

Disclosed are novel cathepsin S, K, F, L and B reversible inhibitory compounds of the formulas (I), (II), (Ia) and (Ib) further defined herein. The compounds are useful for treating autoimmune diseases. Also disclosed are processes for making such novel compounds.

Synthesis and protein kinase C inhibitory activities of balanol analogues with modification of 4-hydroxybenzamido moiety

A series of racemic balanol analogues with modification of the benzamido moiety of balanol have been synthesized and evaluated for their inhibitory activities against human protein kinase C isozymes (PKC-alpha, -beta I, -beta II, -gamma, -delta, -epsilon, and -eta). The structural modification includes replacement of the 4-hydroxyphenyl group with variously substituted phenyl rings, substitution of the amide linkage with a sulfonamide or an ester, and replacement of the 4-hydroxyphenyl substructure with a hydroxyl substituted indole or a hydroxybenzyl group. In general, these analogues were found to be less potent than balanol, but a number of analogues were identified with improved isozyme selectivity. The structure-activity relationship studies of these analogues also indicated that (1) the optimal general PKC inhibition requires a free 4-hydroxyl group in the benzamido portion of the molecule, (2) the amide linkage of the benzamido moiety is important for PKC inhibition, and (3) the conformation associated with the benzamido moiety seems to have a profound effect on PKC inhibition. The requirement of a free 4-hydroxyl group in conjunction with an appropriate conformation of the benzamido moiety for optimal PKC inhibition suggests that the 4-hydroxyphenyl group may be involved in a specific inhibitor-enzyme interaction important for PKC inhibition.