5398-91-4

Basic information

• Product Name: (naphthalen-1-ylsulfanyl)acetonitrile
• CAS NO: 5398-91-4
• Molecular Formula: C₁₂H₉NS
• Molecular Weight: 199.2716
• Mol File: 5398-91-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 374.8°C at 760 mmHg
• Flash Point: 180.5°C
• Density: 1.2g/cm³
• Vapor Pressure: 8.13E-06mmHg at 25°C
• Refractive Index: 1.669
• CAS DataBase Reference: (naphthalen-1-ylsulfanyl)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (naphthalen-1-ylsulfanyl)acetonitrile(5398-91-4)
• EPA Substance Registry System: (naphthalen-1-ylsulfanyl)acetonitrile(5398-91-4)

Safety Data

• Hazardous Substances Data: 5398-91-4(Hazardous Substances Data)

Usage

General Description

"(naphthalen-1-ylsulfanyl)acetonitrile" is a chemical compound that consists of a naphthalene ring with a sulfur atom attached to it, connected to an acetonitrile group. It is a member of the nitrile functional group, which consists of a carbon triple-bonded to a nitrogen. (naphthalen-1-ylsulfanyl)acetonitrile has potential applications in organic synthesis and chemical reactions due to the presence of both the naphthalene and acetonitrile moieties, which can participate in various chemical reactions. It may also have uses in pharmaceuticals, agrochemicals, and materials science due to its unique structural features. Further research and development may uncover additional uses and properties of this compound.

Upstream product

• 529-36-2 1-Naphthalenethiol 
• 590-17-0 cyanomethyl bromide 
• 107-14-2 chloroacetonitrile 

Downstream Products

• 861612-00-2 2-(naphthalen-1-ylsulfonyl)-1-phenylethan-1-one 
• 91258-54-7 N-Hydroxy-2-(naphthalen-1-ylsulfanyl)-acetamidine 

Relevant articles and documents

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).

Rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/ arylsulfonyl)acetonitriles: Efficient synthesis of (Z)-β- sulfonylvinylamines and β-Keto sulfones

An efficient rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/arylsulfonyl)acetonitrile is described. Novel β-sulfonylvinylamine products are formed in a stereoselective fashion (Z-alkene). Upon hydrolysis, useful β-keto sulfones are obtained with a broad scope of aryl and sulfonyl substituents.

Synthesis of arylthioacetamidoximes as potential antidepressants

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