1851-09-8

Basic information

• Product Name: 4-CHLOROPHENYLSULFONYLACETONITRILE
• Synonyms: 2-[(4-CHLOROPHENYL)SULFONYL]ACETONITRILE;(4-CHLOROBENZENESULPHONYL)ACETONITRILE;4-CHLOROBENZENESULFONYLACETONITRILE;4-CHLOROPHENYL CYANOMETHYL SULFONE;4-CHLOROPHENYLSULFONYLACETONITRILE;BUTTPARK 154\04-100;P-CHLOROPHENYLSULFONYL ACETONITRILE;OTAVA-BB BB7719100006
• CAS NO: 1851-09-8
• Molecular Formula: C₈H₆ClNO₂S
• Molecular Weight: 215.66
• Product Categories: Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry
• Mol File: 1851-09-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 168-172 °C
• Boiling Point: 421.2 °C at 760 mmHg
• Flash Point: 208.6 °C
• Appearance: white powder
• Density: 1.409
• Vapor Pressure: 2.64E-07mmHg at 25°C
• Refractive Index: 1.6300 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water.
• BRN: 1819678
• CAS DataBase Reference: 4-CHLOROPHENYLSULFONYLACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLOROPHENYLSULFONYLACETONITRILE(1851-09-8)
• EPA Substance Registry System: 4-CHLOROPHENYLSULFONYLACETONITRILE(1851-09-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22
• Safety Statements: 37/39
• RIDADR: 3276
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1851-09-8(Hazardous Substances Data)

Usage

Description

4-CHLOROPHENYLSULFONYLACETONITRILE is an organic compound with the chemical formula C8H6ClNO2S. It is a white powder and is known for its reactivity with trimethoxymethyl-benzene, resulting in the formation of 2-(4-chloro-benzenesulfonyl)-3-methoxy-3-phenyl-acrylonitrile.

Uses

Used in Chemical Synthesis:
4-CHLOROPHENYLSULFONYLACETONITRILE is used as a key intermediate in the synthesis of various organic compounds. Its reactivity with trimethoxymethyl-benzene allows for the production of 2-(4-chloro-benzenesulfonyl)-3-methoxy-3-phenyl-acrylonitrile, which can be further utilized in the development of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-CHLOROPHENYLSULFONYLACETONITRILE is used as a building block for the synthesis of various drug molecules. Its unique chemical properties make it a valuable component in the development of new medications, particularly those targeting specific biological pathways or receptors.
Used in Agrochemical Industry:
4-CHLOROPHENYLSULFONYLACETONITRILE is also utilized in the agrochemical industry for the synthesis of novel pesticides and other crop protection agents. Its chemical structure can be modified to create compounds with specific modes of action, enhancing the effectiveness of these products in controlling pests and diseases in agriculture.
Used in Research and Development:
Due to its unique chemical properties and reactivity, 4-CHLOROPHENYLSULFONYLACETONITRILE is a valuable compound in research and development laboratories. Scientists and chemists use it to explore new reaction pathways, develop innovative synthetic methods, and create novel compounds with potential applications in various industries.

InChI:InChI=1/C8H6ClNO2S/c9-7-1-3-8(4-2-7)13(11,12)6-5-10/h1-4H,6H2

Upstream product

• 3533-66-2 2,3-dichloroacrylonitrile 
• 14752-66-0 sodium p-chlorobenzenesulphinate 
• 107-14-2 chloroacetonitrile 
• 18527-19-0 4-chlorophenylthioacetonitrile 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 106-54-7 p-Chlorothiophenol 
• 637-87-6 1-Chloro-4-iodobenzene 
• 1624363-23-0 3-azido-2-methylbut-3-en-2-ol 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 

Downstream Products

• 70661-64-2 2-(4-chloro-benzenesulfonyl)-N-hydroxy-acetamidine 
• 59865-87-1 2-(4-chloro-benzenesulfonyl)-thioacetamide 
• 89892-09-1 dichloro-(4-chloro-benzenesulfonyl)-acetonitrile 
• 74755-02-5 (4-chloro-benzenesulfonyl)-hydroxyimino-acetonitrile 
• 128277-21-4 4-Chloro-2-(4-chloro-benzenesulfonylmethyl)-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidine 
• 128277-22-5 2-(4-Chloro-benzenesulfonylmethyl)-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-ylamine 
• 91225-80-8 2-(4-Chloro-benzenesulfonylmethyl)-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 
• 77445-02-4 1-Butyl-3-(4-chloro-benzenesulfonyl)-4,5-dimethyl-1H-pyrrol-2-ylamine 
• 32083-31-1 (E)-3-Amino-2-(4-chloro-benzenesulfonyl)-acrylonitrile 
• 132275-59-3 2-(4-Chloro-benzenesulfonyl)-2-cyano-N-(4-iodo-phenyl)-thioacetamide 
• 77445-03-5 3-(4-Chloro-benzenesulfonyl)-1-cyclohexyl-4,5-dimethyl-1H-pyrrol-2-ylamine 
• 77445-04-6 1-Benzyl-3-(4-chloro-benzenesulfonyl)-4,5-dimethyl-1H-pyrrol-2-ylamine 
• 112381-92-7 ethyl 2-amino-3-(p-chlorophenylsulfonyl)-4,5-dimethylpyrrole-1-acetate 
• 94143-03-0 (E)-3-Amino-2,4-bis-(4-chloro-benzenesulfonyl)-but-2-enenitrile 

Relevant articles and documents

Unexpected Aldehyde-Catalyzed Reaction of Imidazole N -Oxides with Ethyl Cyanoacetate

The reaction of 2-unsubstituted imidazole N -oxides with ethyl cyanoacetate and aromatic aldehydes leads to the formation of ethyl 2-cyano-2-(1,3-dihydro-2 H -imidazole-2-ylidene)acetates. The reaction proceeds through an initial [3+2] cycloaddition, followed by cleavage of the cycloadduct and regeneration of the aldehyde, which essentially plays a catalytic role.

Photoinduced synthesis of 2-sulfonylacetonitriles with the insertion of sulfur dioxide under ultraviolet irradiation

Metal-free insertion of sulfur dioxide with aryl iodides and 3-azido-2-methylbut-3-en-2-ol under ultraviolet irradiation at room temperature is achieved, giving rise to 2-(arylsulfonyl)acetonitriles in moderate to good yields. Alkyl iodide is also workable under these conditions. This transformation proceeds smoothly under mild conditions with a broad substrate scope. Various functional groups are compatible including amino, ester, halo, and trifluoromethyl groups. No metal catalyst or additive is needed during the reaction process. Mechanistic studies show that under ultraviolet irradiation, an aryl radical is generated in situ from aryl iodide, which undergoes subsequent sulfonylation via the insertion of sulfur dioxide leading to arylsulfonyl radical intermediates. Then the arylsulfonyl radical reacts with 3-azido-2-methylbut-3-en-2-ol giving rise to the corresponding 2-(arylsulfonyl)acetonitrile.

Synthesis and biological evaluation of triazolothienopyrimidine derivatives as novel HIV-1 replication inhibitors

We identified a novel class of triazolothienopyrimidine (TTPM) compounds as potent HIV-1 replication inhibitors during a high-throughput screening campaign that evaluated more than 200,000 compounds using a cell-based full replication assay. Herein, we report the optimization of the antiviral activity in a cell-based assay system leading to the discovery of aryl-substituted TTPM derivatives (38, 44, and 45), which exhibited significant inhibition of HIV-1 replication with acceptable safety margins. These novel and potent TTPMs could serve as leads for further development.