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

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

Uses

Used in Pharmaceutical Industry:
2-CHLORO-4-SULFAMOYLANILINE is used as a chemical intermediate for the synthesis of various pharmaceuticals, leveraging its electron-withdrawing and nucleophilic nature to facilitate the creation of new drug compounds.
Used in Dye Industry:
In the dye industry, 2-CHLORO-4-SULFAMOYLANILINE is utilized as a precursor in the production of dyes, capitalizing on its chemical properties to develop dyes with specific color characteristics and properties.
Used in Antimicrobial Applications:
2-CHLORO-4-SULFAMOYLANILINE is employed for its antimicrobial and antibacterial properties, serving as a component in the development of drugs and dyes that are effective against bacteria and fungi.
Environmental and Health Considerations:
Due to the potential health hazards and environmental impact associated with 2-CHLORO-4-SULFAMOYLANILINE, it is crucial to adhere to proper handling and disposal procedures when working with this chemical compound to mitigate risks and protect both human health and the environment.

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

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

Downstream Products

• 22134-75-4 4-amino-3,5-dichloro-benzenesulfonamide 
• 66756-24-9 C₂₀H₂₉ClN₆O₆S₃ 
• 32586-25-7 2-Chloro-4-sulfamoyl-benzenesulfonyl chloride 
• 729-46-4 4,4'-(dithiodicarbonothioyl)dimorpholine 

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.

Tri-substituted triazoles as potent non-nucleoside inhibitors of the HIV-1 reverse transcriptase

A new series of 1,2,4-triazoles was synthesized and tested against several NNRTI-resistant HIV-1 isolates. Several of these compounds exhibited potent antiviral activities against efavirenz- and nevirapine-resistant viruses, containing K103N and/or Y181C mutations or Y188L mutation. Triazoles were first synthesized from commercially available substituted phenylthiosemicarbazides, then from isothiocyanates, and later by condensing the desired substituted anilines with thiosemicarbazones.

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.

HIV REVERSE TRANSCRIPTASE INHIBITORS

Tetrazolyl derivatives of Formula I: are HIV reverse transcriptase inhibitors, wherein U is O, S(O)n where n is an integer equal to zero, 1 or 2, or N(R4); V is optionally substituted C1-8 alkylene; W is C(O)N(R2) or a direct bond linking V to R3; and R1, R2, R3 and R4 are defined herein. The derivatives of Formula I are useful in the inhibition of HIV reverse transcriptase, the prevention and treatment of infection by HIV and in the prevention, delay in the onset, and treatment of AIDS. The derivatives are employed against HIV infection and AIDS as compounds per se or in the form of pharmaceutically acceptable salts. The derivatives 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.

Kinetic of halogenation of Sulphacetamide and Sulphanilamide by Trichloroisocyanuric Acid

Halogenation of sulphacetamide and sulphanilamide by trichloroisocyanuric (TCICA) in aqueous acetic acid-perchloric acid medium is pseudo-first order in and fractional order in .The reaction is first order in and fractional order in .Change of dielectric constant of the medium has a marginal effect on the reaction rate.However, addition of NaCl enhances the rate in both the cases.A plausible mechanism has been suggested to account for the observed kinetics.