19158-51-1

Basic information

• Product Name: Tosyl cyanide
• Synonyms: p-tolylsulfonylforMonitrile;p-Toluenesulfonyl cyanide technical grade, 95%;Toluene-4-sulphonylcyanide,tech;P-TOLYLSULFONYL CYANIDE;p-toluenesulphonyl cyanide;P-TOLUENESULFONYL CYANIDE;TOSYL CYANIDE;4-Toluenesulfonyl Cyanide
• CAS NO: 19158-51-1
• Molecular Formula: C₈H₇NO₂S
• Molecular Weight: 181.21
• EINECS: 242-849-1
• Product Categories: Building Blocks;C8 to C9;Chemical Synthesis;Cyanides/Nitriles;Nitrogen Compounds;Organic Building Blocks
• Mol File: 19158-51-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 47-50 °C(lit.)
• Boiling Point: 105-106 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.3055 (rough estimate)
• Vapor Pressure: 0.0125mmHg at 25°C
• Refractive Index: 1.5650 (estimate)
• Storage Temp.: 2-8°C
• BRN: 2048159
• CAS DataBase Reference: Tosyl cyanide(CAS DataBase Reference)
• NIST Chemistry Reference: Tosyl cyanide(19158-51-1)
• EPA Substance Registry System: Tosyl cyanide(19158-51-1)

Safety Data

• Hazard Codes: C
• Statements: 20/21-34
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 19158-51-1(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Different sources of media describe the Uses of 19158-51-1 differently. You can refer to the following data:
1. p-Toluenesulfonyl cyanide can be used in:The preparation of polyfunctional nitriles.Free-radical cyanation of B-alkylcatecholboranes.The synthesis of 4-hyroxypyridines by hetero-Diels-Alder reaction with 1,3-bis-silyl enol ethers.
2. Tosyl cyanide is used in a free-radical cyanation of B-alkylcatecholboranes. Also used as a component in a hetero-Diels-Alder reaction with 1,3-bis-silyl enol ethers leading to 4-hyroxypyridines.

Synthesis Reference(s)

Tetrahedron Letters, 10, p. 3351, 1969 DOI: 10.1017/S0009838800024678

General Description

p-Toluenesulfonyl cyanide is an electron-deficient nitrile. It undergoes hetero-Diels-Alder reaction with silyl enol ether of cyclohexenone to yield hydrolytically sensitive [4+2] adduct. It also undergoes facile [2+3] cycloaddition reaction with azides to form 5-sulfonyl tetrazoles. p-Toluenesulfonyl cyanide also reacts with alcohols in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,4-diazabicyclo[2.2.2]octane (DABCO) to yield sulfinates.

InChI:InChI=1/C9H14N2/c1-11(2)9-5-3-8(7-10)4-6-9/h3-6H,7,10H2,1-2H3

Upstream product

• 824-79-3 sodium 4-methylbenzenesulfinate 
• 506-77-4 cyanogen chloride 
• 5285-74-5 4-tolyl thiocyanate 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 51915-25-4 C₉H₁₀ClNO₂S₂ 
• 51915-23-2 C₁₆H₁₄Cl₂N₂O₄S₃ 
• 142272-77-3 1,9-Dimethyl-3-(toluene-4-sulfonyl)-9H-β-carboline 
• 133523-50-9 4-methyl-3-(p-toluenesulfonyl)-1,2,4-thiadiazoline-5-thione 
• 35274-27-2 2-(p-tolylsulphonylmethyl)hexanenitrile 
• 112033-21-3 2-Butyl-4-(toluene-4-sulfonylmethyl)-octanenitrile 
• 112033-24-6 exo-2-cyano-exo-6-(p-tolylsulphonyl)bicyclo<3.3.0>octane 
• 263-06-9 6H,12H-Dibenzo<1,5>dithiocin 
• 135216-84-1 2-(4-Methylphenylsulfonyl)-4H-1,3-benzothiazine 
• 30515-63-0 N-cyclohexylidene-4-methylbenzenesulfonamide 
• 10399-00-5 benzophenone tosylimine 
• 112052-19-4 (Z)-(1R,4R)-4-(Toluene-4-sulfonyl)-cyclooct-2-enecarbonitrile 
• 51954-52-0 5-methyl-2-tosylpyridine 
• 1517-82-4 (-)-menthyl p-toluenesulfinate 

Related news

A novel sulfinylation of alkenes by Tosyl cyanide (cas 19158-51-1) with titanium(IV) chloride07/25/2019

Tosyl cyanide is activated by titanium(IV) chloride to generate a tolylsulfinyl chloride equivalent, which readily stereo- and regio-specifically adds to certain alkenes to provide β-chlorosulfoxides. These chlorides rapidly hydrolyse on silica gel to provide β-hydroxysulfoxides in stereocontr...detailed

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