97-08-5

Basic information

• Product Name: 4-Chloro-3-nitrobenzenesulfonyl chloride
• Synonyms: 3-NITRO-4-CHLOROBENZENESULFONYL CHLORIDE;3-NITRO-4-CHLOROBENZENSULFONYL CHLORIDE;4-CHLORO-3-NITROBENZENE-1-SULFONYL CHLORIDE;4-CHLORO-3-NITROBENZENESULFONYL CHLORIDE;4-CHLORO-3-NITROBENZENESULPHONYL CHLORIDE;2-CHLORO-1-NITROBENZENE-5-SULFONYL CHLORIDE;YELLOW SULFON CHLORIDE;4-chloro-3-nitro-benzenesulfonylchlorid
• CAS NO: 97-08-5
• Molecular Formula: C₆H₃Cl₂NO₄S
• Molecular Weight: 256.06
• EINECS: 202-558-2
• Product Categories: Intermediates of Dyes and Pigments;Benzene derivates;Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds;NULL
• Mol File: 97-08-5.mol

Chemical Properties

• Melting Point: 59-60 °C(lit.)
• Boiling Point: 356°C (rough estimate)
• Flash Point: 169.1 °C
• Appearance: Light brown/Crystalline Powder
• Density: 1.696 (estimate)
• Vapor Pressure: 6.17E-05mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Toluene
• Sensitive: Moisture Sensitive
• BRN: 1978600
• CAS DataBase Reference: 4-Chloro-3-nitrobenzenesulfonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-3-nitrobenzenesulfonyl chloride(97-08-5)
• EPA Substance Registry System: 4-Chloro-3-nitrobenzenesulfonyl chloride(97-08-5)

Safety Data

• Hazard Codes: C
• Statements: 34-29-14
• Safety Statements: 26-27-28-36/37/39-45-8-30-22
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 97-08-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-3-nitrobenzenesulfonyl chloride is used as a synthetic intermediate for the preparation of novel sulfonamide derivatives of tricyclic thieno[2,3-d]pyrimidin-4(3H)-ones, which are known to increase melanin synthesis in murine B16 cells. This application is significant in the development of treatments for skin pigmentation disorders and other related conditions.
Used in Organic Synthesis:
In the field of organic synthesis, 4-chloro-3-nitrobenzenesulfonyl chloride serves as a key starting material for the preparation of functionalized 1H-indenes through copper-catalyzed arylative cyclization. This process is crucial for the synthesis of complex organic molecules with potential applications in various industries.
Used in Pesticide Development:
4-Chloro-3-nitrobenzenesulfonyl chloride is also utilized as a precursor in the synthesis of N-arylsulfonyl-3-acylindole arylcarbonyl hydrazone derivatives. These compounds have demonstrated potential nematicidal activity, making them valuable in the development of new pesticides for controlling nematode pests in agriculture.
Used in Cancer Research:
As a key component in the synthesis of sulfonamide analogs of ferrostatin-1 (fer-1), 4-chloro-3-nitrobenzenesulfonyl chloride contributes to the development of compounds with good ferroptosis inhibition properties. Ferroptosis is a form of regulated cell death, and its inhibition may have implications in cancer research and therapy.
Used in Chemical Synthesis:
In addition to its applications in pharmaceuticals and organic synthesis, 4-chloro-3-nitrobenzenesulfonyl chloride is also used in the synthesis of 4-chloro-3-nitrobenzene thiol, a compound that can be further utilized in various chemical reactions and processes.
Overall, 4-chloro-3-nitrobenzenesulfonyl chloride is a versatile compound with applications spanning across pharmaceuticals, organic synthesis, pesticide development, cancer research, and other chemical processes. Its reactivity and ability to serve as a synthetic intermediate make it a valuable component in the development of new compounds and materials.

InChI:InChI=1/C6H3Cl2NO4S/c7-5-2-1-4(14(8,12)13)3-6(5)9(10)11/h1-3H

Upstream product

• 121-18-6 3-nitro-4-chlorobenzenesulfonic acid 
• 88-73-3 2-Chloronitrobenzene 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 17691-19-9 4-chloro-3-nitrobenzenesulphonic acid sodium salt 
• 7790-94-5 chlorosulfonic acid 
• 119-00-6 2-nitro-1,4-benzenedisulfonic acid 
• 10026-13-8 phosphorus pentachloride 
• 98-66-8 4-chloro-benzenesulfonic acid 
• 6671-49-4 4-chloro-3-nitro-benzenesulfonic acid ; potassium-salt 
• 5329-14-6 aminosulfonic acid 
• 635-22-3 4-Chloro-3-nitroaniline 

Downstream Products

• 53162-43-9 1-(4-chloro-3-nitro-benzenesulfonyl)-piperidine 
• 94428-01-0 4-chloro-3-nitro-benzenesulfonic acid-[2]pyridylamide 
• 43001-57-6 3-nitro-4-chloro-benzene sulfonic acid phenyl ester 
• 6655-80-7 4-chloro-3-nitrobenzenesulfonylhydrazine 
• 35964-48-8 1,1'-disulphanediylbis(4-chloro-3-nitrobenzene) 
• 97-09-6 4-Chloro-3-nitrobenzenesulfonamide 
• 248277-40-9 N-chlorophenyl-4-chloro-3-nitrobenzenesulfonamide 
• 101251-02-9 N-(3-nitro-4-chlorophenylsulfonyl)ethanolamine 
• 51929-55-6 3-amino-4-phenoxy-benzenesulfonic acid-(N-ethyl-anilide) 
• 137-47-3 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide 
• 96-59-3 4-chloro-3-nitro-benzenesulfonic acid isopropylamide 
• 96-61-7 4-chloro-3-nitro-N-butylbenzenesulfonamide 
• 42800-25-9 2-amino-4-(4-chloro-benzenesulfonyl)-phenol 
• 30751-24-7 4-chloro-3-nitro-benzenesulfonic acid-(2-hydroxy-anilide) 

Relevant articles and documents

Amplified synthesis method of 3-nitro-4-halogeno-benzenesulfonamide

An amplified synthesis method of 3-nitro-4-halogeno-benzenesulfonamide is disclosed. According to the method, 4-halogeno-benzenesulfonyl chloride which is used as a raw material undergoes nitration to prepare 3-nitro-4-halogeno-benzenesulfonyl chloride; and after aminolysis, 3-nitro-4-halogeno-benzenesulfonamide is prepared. By the synthesis method provided by the invention, the synthesis route by the adoption of chlorosulfonic acid is changed, and production safety is remarkably raised. The reaction condition is milder and is easy for production control. Thus, mass production of the compound is easier to implement and realize.

ANTICOAGULANT COMPOUNDS, PHARMACEUTICAL COMPOSITIONS ON THEIR BASIS TO TREAT THROMBOTIC CONDITIONS, AND PLASMA-SUBSTITUTING SOLUTION TO CORRECT HYPERCOAGULATION DEFECTS OF HEMODILUTION

This invention relates to new chemical compounds, application of these compounds as anticoagulants, pharmaceutical compositions, and plasma-substituting solutions on their basis, and can be used for treating thromboembolic complications of diseases such as myocardial infarction, stroke, and thrombosis of deep veins or a pulmonary artery; and for preventing hypercoagulation conditions in consequence of injuries, surgeries, sepsis, various obstetric pathologies, in disaster medicine, resuscitation, and so on.

THROMBIN FUNCTION COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS BASED ON THEM

This invention relates to new chemical compounds, application of these compound as thrombin inhibitors, and pharmaceutical compositions based on them, and can be used to treat and prevent thrombin-dependent thromboembolic events, and in research.

Synthesis and Antitubulin Activity of N1- and N 4-Substituted 3,5-Dinitro Sulfanilamides against African Trypanosomes and Leishmania

Thirty analogues of N1-phenyl-3,5-dinitro-N4,N 4-di-n-propylsulfanilamide (GB-II-5, compound 3), a new antikinetoplastid antimitotic agent, have been synthesized and evaluated. The addition of simple functional groups to the N1 aromatic ring generally decreases antiparasitic and antimitotic potency, but placement of a dibutyl substituent at the N4 nitrogen to give N1-phenyl-3,5-dinitro-N 4,N4-di-n-butylsulfanilamide (compound 35) augments antitrypanosomal and antileishmanial activity. Compound 35 possesses IC 50 values of 0.12 and 2.6 μM against cultured T. brucei and L. donovani amastigote-like forms, surpassing the activity of compound 3 against these parasites by 3.4- and 1.9-fold, respectively. Compound 35 inhibits the assembly of leishmanial tubulin with an IC50 of 6.9 μM and displays antimitotic effects in cultured T. brucei as assessed by flow cytometry, but shows little effect on purified mammalian tubulin, and displays 100-fold selectivity for trypanosomes over two mammalian cell lines. Although 3 and 35 were not effective in initial in vivo antitrypanosomal assays, the in vitro potency and selectivity of these compounds make N 1-aryl-3,5-dinitro-N4,N4-dialkylsulfanilamides a promising new class of antikinetoplastid agents that act on parasite tubulin.

Tetrahydropyran derivatives

A novel tetrahydropyran derivative which has an excellent apo B-related lipoprotein secretion-inhibiting activity of the following general formula (I) or a salt thereof: R8 and R9 are the same or different and each represents H, lower alkyl, R30-lower alkyl-, R31R32N-, optionally- substituted hetero ring, or R33R34R35C-; R8 and R9 may together form optionally-substituted hetero ring-; R30 represents optionally-substituted aryl, optionally-substituted hetero ring-, or lower alkyl-O-; R31 represents optionally-substituted aryl, or optionally-substituted hetero ring-; R33 represents HO-lower alkyl-, or optionally-substituted hetero ring-lower alkyl-; R34 represents optionally-substituted aryl-.

Antileishmanial dinitroaniline sulfonamides with activity against parasite tubulin.

Novel dinitroaniline sulfonamides based on the herbicide oryzalin 3 were synthesized and evaluated for activity against the parasitic protozoan Leishmania donovani and against leishmanial tubulin, the putative antiparasitic target of oryzalin. A subset of these compounds possess more activity against both Leishmania and the target protein in vitro. Compound 20 displays improved potency against leishmanial tubulin and is 13.4-fold more active against L. donovani axenic amastigotes than oryzalin.

2-aryl-4-isoxazolin-3-one derivatives

2-aryl-4-isoxazolin-3-1-derivatives of formula (I), useful as intermediates for positive working compounds in silver halide photographic materials STR1 wherein R1 represents a substituted or unsubstituted alkyl having from 1 to 6 carbon atoms or a substituted or unsubstituted aryl having from 6 to 24 carbon atoms; and R2, R3, and R4, are the same or different, each having up to 20 carbon atoms and each represents hydrogen, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted acyl, a substituted or unsubstituted alkoxycarbonyl, a substituted or unsubstituted aryloxycarbonyl, halogen, nitro, a substituted or unsubstituted carbamoyl, a substituted or unsubstituted sulfamoyl, a substituted or unsubstituted sulfonyl, cyano, or trifluoromethyl, with the proviso that at least one of said R2 and R3 is cyano, a substituted or unsubstituted sulfonyl, trifluoromethyl, or nitro.

Process for the preparation of aromatic sulfonyl chlorides

A process for the preparation of aromatic sulfonyl chlorides of the formula I STR1 in which R1, R2 and R3 are identical or different and are hydrogen, fluorine, chlorine, bromine or iodine atoms, alkyl(C1 -C4), acetamido, nitro or carboxyl groups, or R1 and R2 together form an aromatic or heteroaromatic ring having 5 or 6 ring members, which can be substituted by fluorine, chlorine, bromine or iodine atoms, alkyl(C1 -C4), acetamido, nitro or carboxyl groups, by reaction of aromatic compounds of the formula II STR2 in which R1, R2 and R3 have the abovementioned meanings, with chlorosulfonic acid in excess or with chlorosulfonic acid or oleum and thionyl chloride, by reacting in the presence of sulfamic acid as a catalyst.

2-aryl-4-halomethyl-4-isoxazolin-3-one derivatives

2-aryl-4-halomethyl-4-isoxazolin-3-1-derivatives of formula (I), useful as intermediates for positive working compounds in silver halide photographic materials STR1 wherein R1 represents a substituted or unsubstituted alkyl having from 1 to 6 carbon atoms or a substituted or unsubstituted aryl having from 6 to 24 carbon atoms; R2, R3, and R4, are the same or different, each having up to 20 carbon atoms and each represents hydrogen, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted acyl, a substituted or unsubstituted alkoxycarbonyl, a substituted or unsubstituted aryloxycarbonyl, halogen, nitro, a substituted or unsubstituted carbamoyl, a substituted or unsubstituted sulfamoyl, a substituted or unsubstituted sulfonyl, cyano, trifluoromethyl, or carboxyl, with the proviso that at least one of said R2 and R3 is cyano, a substituted or unsubstituted sulfonyl, trifluoromethyl, or nitro; and X represents fluorine, chlorine, bromine or iodine.