53297-68-0

Basic information

• Product Name: 2-CHLORO-4-SULFAMOYLANILINE
• Synonyms: 4-amino-3-chloro-benzenesulfonamid;4-amino-3-chlorobenzenesulfonamide;3-14-00-02189 (Beilstein Handbook Reference);Benzenesulfonamide, 4-amino-3-chloro-;2-CHLORO-4-SULFAMOYLANILINE
• CAS NO: 53297-68-0
• Molecular Formula: C₆H₇ClN₂O₂S
• Molecular Weight: 206.65
• Product Categories: pharmacetical
• Mol File: 53297-68-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 161 °C
• Boiling Point: 414.4 °C at 760 mmHg
• Flash Point: 204.4 °C
• Appearance: /
• Density: 1.558 g/cm³
• Vapor Pressure: 4.46E-07mmHg at 25°C
• Refractive Index: 1.637
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 9.83±0.60(Predicted)
• CAS DataBase Reference: 2-CHLORO-4-SULFAMOYLANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-4-SULFAMOYLANILINE(53297-68-0)
• EPA Substance Registry System: 2-CHLORO-4-SULFAMOYLANILINE(53297-68-0)

Safety Data

• Hazardous Substances Data: 53297-68-0(Hazardous Substances Data)

Usage

General Description

2-CHLORO-4-SULFAMOYLANILINE is a chemical compound that consists of a chloro group and a sulfamoyl group attached to an aniline ring. It is commonly used as an intermediate in the synthesis of various pharmaceuticals and dyes due to its strong electron-withdrawing and nucleophilic nature. 2-CHLORO-4-SULFAMOYLANILINE is also known for its antimicrobial and antibacterial properties, and it is used in the production of drugs and dyes that are effective against bacteria and fungi. Due to its potential health hazards and environmental impact, proper handling and disposal procedures are necessary when working with 2-CHLORO-4-SULFAMOYLANILINE.

InChI:InChI=1/C6H7ClN2O2S/c7-5-3-4(12(9,10)11)1-2-6(5)8/h1-3H,8H2,(H2,9,10,11)

Upstream product

• 68252-72-2 4-acetamido-3-chlorobenzenesulfonamide 
• 95-51-2 o-chloroaniline 
• 16761-18-5 4-acetamido-3-chlorobenzenesulphonyl chloride 
• 533-17-5 N-(2-chlorophenyl)acetamide 
• 63-74-1 sulfanilamide 

Downstream Products

• 137-26-8 Thiram 

Relevant articles and documents

Synthesis method of 2-chloro-6-bromaniline

The invention relates to a synthesis method of 2-chloro-6-bromaniline and belongs to the field of chemical synthesis. The synthesis method comprises the following steps: by taking simple sulfonamide as a starting raw material, carrying out selective single halogenation reaction on sulfonamide, so that the 2-chloro-6-bromaniline is obtained through three-step reaction, wherein yield of the halogenation reaction is more than or equal to 80% respectively, and a structure is confirmed by virtue of 1H NMR and 13C NMR. The synthesis method provided by the invention has the advantages that sulfanilamide which is simpler and easier to get compared with m-chlorobromobenzene can be taken as a raw material, the 2-chloro-6-bromaniline is provided with high yield under relatively mild conditions, synthesis of 2-chloro-6-bromaniline analogues also can be expanded, namely the same or different halogens are introduced to sites 2,6- of phenylamine, and phenylamine analogues substituted by different halogens can be obtained by virtue of a synthesis route.

HIV REVERSE TRANSCRIPTASE INHIBITORS

Compounds of Formula (I) are HIV reverse transcriptase inhibitors, wherein T is O or S; U is O, S, N(R4), or a direct bond linking V to the C(=T) moiety; V is optionally substituted C1-6 alkylene; W is C(O)N(R5) or a direct bond linking V to R3; and R1, R2, R3, R4 and R5 are defined herein. The compounds of Formula (I) and their pharmaceutically acceptable salts are useful in the inhibition of HIV reverse transcriptase, the prophylaxis and treatment of infection by HIV and in the prophylaxis, delay in the onset, and treatment of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.

Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX by halogenosulfanilamide and halogenophenylaminobenzolamide derivatives

Two series of halogenated sulfonamides have been prepared. The first consists of mono/ dihalogenated sulfanilamides, whereas the second one consists of the mono/dihalogenated aminobenzolamides, incorporating equal or different halogens (F, Cl, Br, and I). These sulfonamides have been synthesized from the corresponding anilines by acetylation (protection of the amino group), chlorosulfonylation, followed either by amidation, or reaction with 5-amino1,3,4-thiadiazole-2-sulfonamide (and eventually deacetylation). All these compounds, together with the six clinically used sulfonamide inhibitors (acetazolamide, methazolamide, ethoxzolamide, dichlorophenamide, dorzolamide, and brinzolamide) were investigated as inhibitors of the transmembrane, tumor-associated isozyme carbonic anhydrase (CA) IX. Inhibition data against the classical, physiologically relevant isozymes I, II, and IV were also obtained. CA IX shows an inhibition profile which is generally completely different from those of isozymes I, II, and IV, with potent inhibitors (inhibition constants in the range of 12-40 nM) among both simple aromatic (such as 3-fluoro-5-chloro-4-aminobenzenesulfonamide) as well as heterocyclic compounds (such as acetazolamide, methazolamide, 5-amino-1,3,4-thiadiazole-2-sulfonamide, aminobenzolamide, and dihalogenated aminobenzolamides). This first detailed CA IX inhibition study revealed many interesting leads, suggesting the possibility to design even more potent and eventually CA IX-selective inhibitors, with putative applications as antitumor agents.