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

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

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

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

Downstream Products

• 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 
• 94143-06-3 (Z)-3-Amino-2,4-bis-(4-chloro-benzenesulfonyl)-but-2-enenitrile 
• 113525-47-6 2-amino-3-(p-chlorophenylsulfonyl)-4,5-dimethylfuran 
• 94123-51-0 6,7-Dimethyl-8-(p-chlorophenylsulfonyl)-2-oxo-1,2,3,4-tetrahydropyrrolo<1,2-a><1,3>pyrimidine 
• 34221-60-8 2-(4-Chloro-benzenesulfonyl)-4-(1,2-dichloro-1,2,2-trifluoro-ethanesulfonyl)-2-[2-(1,2-dichloro-1,2,2-trifluoro-ethanesulfonyl)-ethyl]-butyronitrile 
• 34130-16-0 4-(4-Chloro-benzenesulfonyl)-4-cyano-heptanedinitrile 
• 170803-70-0 1-(4-Chloro-benzenesulfonyl)-cyclopropanecarbonitrile 
• 34133-37-4 4-(4-Chloro-benzenesulfonyl)-4-cyano-heptanedioic acid 

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.

Preparation method of sulfonyl acetonitrile compound

The invention belongs to the technical field of organic chemistry, and particularly relates to a preparation method of sulfonyl acetonitrile compounds. The structure of the compound is characterized by 1H NMR, 13C NMR and other methods and is confirmed. The method comprises the following steps: taking 2, 2-dichloroethane as a solvent and aryl diazonium salt and sodium pyrosulfite (Na2S2O5) as a catalyst without metal catalyst, generating aryl sulfonyl free radicals on site at room temperature, carrying out free radical addition reaction on 3-azido-2-methylbutyl-3-ene-2-ol, and removing monomolecular nitrogen and 2-hydroxypropyl free radicals to obtain the sulfonyl acetonitrile compound. The preparation method of the sulfonyl acetonitrile compound has the advantages of being mild in condition, simple, efficient, high in reaction yield, wide in substrate application range, good in product purity, convenient to separate and purify and good in application value.

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.

Inhibitors of the Diadenosine Tetraphosphate Phosphorylase Rv2613c of Mycobacterium tuberculosis

The intracellular concentration of diadenosine tetraphospate (Ap4A) increases upon exposure to stress conditions. Despite being discovered over 50 years ago, the cellular functions of Ap4A are still enigmatic. If and how the varied Ap4A is a signal and involved in the signaling pathways leading to an appropriate cellular response remain to be discovered. Because the turnover of Ap4A by Ap4A cleaving enzymes is rapid, small molecule inhibitors for these enzymes would provide tools for the more detailed study of the role of Ap4A. Here, we describe the development of a high-throughput screening assay based on a fluorogenic Ap4A substrate for the identification and optimization of small molecule inhibitors for Ap4A cleaving enzymes. As proof-of-concept we screened a library of over 42, 000 compounds toward their inhibitory activity against the Ap4A phosphorylase (Rv2613c) of Mycobacterium tuberculosis (Mtb). A sulfanylacrylonitril derivative with an IC50 of 260 ± 50 nM in vitro was identified. Multiple derivatives were synthesized to further optimize their properties with respect to their in vitro IC50 values and their cytotoxicity against human cells (HeLa). In addition, we selected two hits to study their antimycobacterial activity against virulent Mtb to show that they might be candidates for further development of antimycobacterial agents against multidrug-resistant Mtb.

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.

(Arylsulfonyl)acetones and -acetonitriles: New activated methylenic building blocks for synthesis of 1,2,3-triazoles

β-Keto sulfones and b-nitrile sulfones were used as building blocks for 1,2,3-triazole synthesis in the Dimroth cyclization. It was shown, that sulfone reagents undergo base-catalyzed cyclization under mild conditions (at room temperature) to give 1,2,3-triazoles in moderate to excellent yields. This fact has confirmed the high nucleophilicity of sulfonylmethylenic compounds and allows new synthetic applications. Georg Thieme Verlag Stuttgart.

Fast and efficient oxidation of sulfides to sulfones with N,N′-dibenzyl-N,N,N′,N′-tetramethyl diammonium permanganate

Selective oxidation of sulfides to sulfones was developed using N,N′-dibenzyl-N,N,N′,N′-tetramethylethylene diammonium permanganate. A variety of aromatic and aliphatic sulfides were oxidized to the corresponding sulfones immediately in excellent yields at r.t. Copyright Taylor & Francis Group, LLC.

IMIDAZOLE ALKYLAMINOETHYLENE COMPOUNDS

The compounds are ethylene derivatives which are inhibitors of histamine activity, in particular, inhibitors of H-2 histamine receptors. A compound of this invention is 1-nitro-2-methylamino-2-2-((4-methyl-5-imidazolyl)methylthio)-ethylamino!ethylene.