32083-60-6

Basic information

• Product Name: 2-(2-NAPHTHYLSULFONYL)ACETONITRILE
• Synonyms: BUTTPARK 94\04-17;2-(2-NAPHTHYLSULFONYL)ACETONITRILE;2-(2-naphthylsulphonyl)acetonitrile;NAPHTH-2-YLSULFONYLACETONITRILE;[(Naphth-2-yl)sulphonyl]acetonitrile;2-[(Cyanomethyl)sulphonyl]naphthalene
• CAS NO: 32083-60-6
• Molecular Formula: C₁₂H₉NO₂S
• Molecular Weight: 231.27
• Mol File: 32083-60-6.mol

Chemical Properties

• Melting Point: 95.5℃
• Boiling Point: 495.7°Cat760mmHg
• Flash Point: 253.6°C
• Appearance: /
• Density: 1.319g/cm³
• Vapor Pressure: 5.78E-10mmHg at 25°C
• Refractive Index: 1.629
• CAS DataBase Reference: 2-(2-NAPHTHYLSULFONYL)ACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-NAPHTHYLSULFONYL)ACETONITRILE(32083-60-6)
• EPA Substance Registry System: 2-(2-NAPHTHYLSULFONYL)ACETONITRILE(32083-60-6)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 3276
• Hazardous Substances Data: 32083-60-6(Hazardous Substances Data)

Usage

Physical state

White solid

Molecular weight

257.31 g/mol

Uses

Building block in organic synthesis, reagent in chemical reactions, intermediate in production of pharmaceuticals and agrochemicals

Potential applications

Materials science, research tool in organic chemistry

InChI:InChI=1/C12H9NO2S/c13-7-8-16(14,15)12-6-5-10-3-1-2-4-11(10)9-12/h1-6,9H,8H2

Upstream product

• 1624363-23-0 3-azido-2-methylbut-3-en-2-ol 
• 450-58-8 2-naphthyldiazonium tetrafluoroborate 
• 5324-69-6 2-(naphthalen-2-ylthio)acetonitrile 
• 91-60-1 2-Naphthalenethiol 
• 107-14-2 chloroacetonitrile 

Downstream Products

• 132275-89-9 2-Cyano-2-(naphthalene-2-sulfonyl)-N-p-tolyl-thioacetamide 
• 132275-92-4 N-(4-Chloro-phenyl)-2-cyano-2-(naphthalene-2-sulfonyl)-thioacetamide 
• 132275-90-2 2-Cyano-N-(4-methoxy-phenyl)-2-(naphthalene-2-sulfonyl)-thioacetamide 
• 159848-75-6 (S)-3-(N-terc-butoxycarbonylamine)-3-(4-methoxyphenyl)propanenitrile 
• 1630982-10-3 (S)-3-(N-tert-butoxycarbonylamine)-3-(4-fluorophenyl)propanenitrile 
• 1630982-12-5 (S)-3-(N-tert-butoxycarbonylamine)-3-(3-chlorophenyl)propanenitrile 
• 1630982-13-6 (S)-3-(N-tert-butoxycarbonylamine)-3-(2-bromophenyl)propanenitrile 
• 1630982-17-0 (S)-3-(N-tert-butoxycarbonylamine)-3-cyclohexylpropanenitrile 
• 1630982-19-2 (S)-3-(N-tert-butoxycarbonylamine)-3-(4-trifluoromethylphenyl)propanenitrile 
• 126568-44-3 (S)-3-(N-tert-butoxycarbonylamino)-3-phenylpropanenitrile 
• 132276-86-9 3-Amino-4-(naphthalene-2-sulfonyl)-5-(4-nitro-phenylamino)-thiophene-2-carboxylic acid ethyl ester 
• 132276-85-8 3-Amino-5-(4-ethoxy-phenylamino)-4-(naphthalene-2-sulfonyl)-thiophene-2-carboxylic acid ethyl ester 
• 132276-69-8 (Naphthalene-2-sulfonyl)-[3-(4-nitro-phenyl)-4-oxo-thiazolidin-(2Z)-ylidene]-acetonitrile 

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.).

Ureidopeptide-based Bronsted bases: Design, synthesis and application to the catalytic enantioselective synthesis of β-amino nitriles from (arylsulfonyl)acetonitriles

The addition of cyanoalkyl moieties to imines is a very attractive method for the preparation of β-amino nitriles. We present a highly efficient organocatalytic methodology for the stereoselective synthesis of β-amino nitriles, in which the key to success is the use of ureidopeptide-based Bronsted base catalysts in combination with (arylsulfonyl)acetonitriles as synthetic equivalents of the acetonitrile anion. The method gives access to a variety of β-amino nitriles with good yields and excellent enantioselectivities, and broadens the stereoselective Mannich-type methodologies available for their synthesis. Learning from peptides: A concise route for the catalytic enantioselective synthesis of β-amino nitriles has been achieved by using ureidopeptide-based Bronsted bases as catalysts in the Mannich reaction of N-Boc imines and (arylsulfonyl)acetonitriles (see scheme; Boc=tert-butoxycarbonyl, napht=naphthyl, TMS=trimethylsilyl).