5697-44-9

Basic information

• Product Name: 4-(Methylphenyl)sulfonylacetonitrile
• Synonyms: (Toluene-4-sulfonyl)-acetonitrile;Acetonitrile, [(4-methylphenyl)sulfonyl]-;P-TOLUENESULFONYLACETONITRILE;P-TOLUENESULPHONYLACETONITRILE;P-TOLYLSULFONYLACETONITRILE;OTAVA-BB BB0125330361;P-(CYANOMETHYLSULFONYL)TOLUENE;4-TOLUENESULFONYLACETONITRILE
• CAS NO: 5697-44-9
• Molecular Formula: C₉H₉NO₂S
• Molecular Weight: 195.24
• EINECS: 227-173-7
• Mol File: 5697-44-9.mol
• Article Data: 16

Chemical Properties

• Melting Point: 147-151 °C
• Boiling Point: 400.9 °C at 760 mmHg
• Flash Point: 196.3 °C
• Appearance: off-white crystalline powder
• Density: 1.2721 (rough estimate)
• Refractive Index: 1.5270 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 1842131
• CAS DataBase Reference: 4-(Methylphenyl)sulfonylacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Methylphenyl)sulfonylacetonitrile(5697-44-9)
• EPA Substance Registry System: 4-(Methylphenyl)sulfonylacetonitrile(5697-44-9)

Safety Data

• Hazard Codes: Xn,T
• Statements: 20/21/22
• Safety Statements: 36/37
• RIDADR: 3276
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 5697-44-9(Hazardous Substances Data)

Usage

Chemical Properties

off-white crystalline powder

Synthesis Reference(s)

Synthesis, p. 56, 1987 DOI: 10.1055/s-1987-27843Tetrahedron, 23, p. 1145, 1967 DOI: 10.1016/0040-4020(67)85064-6

InChI:InChI=1/C16H10Cl2N2OS/c17-12-6-4-10(5-7-12)14-9-22-16(19-14)20-15(21)11-2-1-3-13(18)8-11/h1-9H,(H,19,20,21)

Upstream product

• 7436-85-3 3,3-dichloro-acrylonitrile 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 3533-66-2 2,3-dichloroacrylonitrile 
• 64-17-5 ethanol 
• 861611-59-8 dibromo-(toluene-4-sulfonyl)-acetonitrile 
• 100-63-0 phenylhydrazine 
• 107-14-2 chloroacetonitrile 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 
• 1584143-93-0 C₁₀H₁₁N₃O 
• 1624363-23-0 3-azido-2-methylbut-3-en-2-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 75-05-8 acetonitrile 
• 106-45-6 para-thiocresol 

Downstream Products

• 175201-58-8 hydroxyimino-(toluene-4-sulfonyl)-acetonitrile 
• 73583-57-0 3,7-Dimethyl-2-(4-methylbenzenesulphonyl)-5-oxo-6-octenenitrile 
• 73583-67-2 (1R,6S)-2,2,6-Trimethyl-4-oxo-1-(toluene-4-sulfonyl)-cyclohexanecarbonitrile 
• 68342-52-9 (Z)-3-Amino-2-(toluene-4-sulfonyl)-acrylonitrile 
• 25979-67-3 2-cyano-N-(4-iodo-phenyl)-2-(toluene-4-sulfonyl)-thioacetamide 
• 77444-97-4 1-Cyclohexyl-4,5-dimethyl-3-(toluene-4-sulfonyl)-1H-pyrrol-2-ylamine 
• 77444-98-5 1-Benzyl-4,5-dimethyl-3-(toluene-4-sulfonyl)-1H-pyrrol-2-ylamine 
• 76283-87-9 5-Oxo-2-(3-oxo-3-phenyl-propyl)-5-phenyl-2-(toluene-4-sulfonyl)-pentanenitrile 
• 113729-70-7 {(1R,2S,6R)-1,2-Dimethyl-6-[4-(toluene-4-sulfonyl)-thiazol-5-ylmethyl]-cyclohexyl}-methanol 
• 77445-01-3 4,5-Dimethyl-1-(3-morpholin-4-yl-propyl)-3-(toluene-4-sulfonyl)-1H-pyrrol-2-ylamine 
• 77445-00-2 4,5-Dimethyl-1-pyridin-3-ylmethyl-3-(toluene-4-sulfonyl)-1H-pyrrol-2-ylamine 
• 77444-99-6 4,5-Dimethyl-1-phenethyl-3-(toluene-4-sulfonyl)-1H-pyrrol-2-ylamine 
• 112381-93-8 ethyl 2-amino-3-(p-toluenesulfonyl)-4,5-dimethylpyrrole-1-acetate 
• 105282-64-2 3-Allyl-9-benzyl-9-aza-bicyclo[4.2.1]nonane-2-carbonitrile 

Relevant articles and documents

A Concise Route to 2-Sulfonylacetonitriles from Sodium Metabisulfite

A three-component reaction of aryldiazonium tetrafluoroborates, sodium metabisulfite, and 3-azido-2-methylbut-3-en-2-ol under mild conditions is described. By using abundant and cheap sodium metabisulfite as the sulfur dioxide surrogate, this protocol features good functional group compatibility, affording 2-arylsulfonylacetonitriles in moderate to good yields. The reaction proceeds smoothly at room temperature without the need of any catalysts or additives. Moreover, the synthetic utility of this method is demonstrated by the transformation of 2-arylsulfonylacetonitrile into 2-arylsulfonyl acetamide and 2-arylsulfonylethylamine. (Figure presented.).

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.