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Tosyl cyanide

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Tosyl cyanide Basic information

Product Name:
Tosyl cyanide
Synonyms:
  • p-tolylsulfonylforMonitrile
  • p-Tosyl cyanide
  • Toluene-4-sulfonyl cyanide 98%
  • p-Toluenesulfonyl cyanide technical grade, 95%
  • Toluene-4-sulphonylcyanide,tech
  • P-TOLYLSULFONYL CYANIDE
  • p-toluenesulphonyl cyanide
  • P-TOLUENESULFONYL CYANIDE
CAS:
19158-51-1
MF:
C8H7NO2S
MW:
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
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Tosyl cyanide Chemical Properties

Melting point:
47-50 °C (lit.)
Boiling point:
105-106 °C/1 mmHg (lit.)
Density 
1.3055 (rough estimate)
refractive index 
1.5650 (estimate)
Flash point:
>230 °F
storage temp. 
2-8°C
BRN 
2048159
CAS DataBase Reference
19158-51-1(CAS DataBase Reference)
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Safety Information

Hazard Codes 
C
Risk Statements 
20/21-34
Safety Statements 
26-27-28-36/37/39-45
RIDADR 
UN 3261 8/PG 2
WGK Germany 
3
10-21
HazardClass 
8
PackingGroup 
III

MSDS

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Tosyl cyanide Usage And Synthesis

Chemical Properties

White powder

Uses

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.

Uses

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.

Tosyl cyanide Preparation Products And Raw materials

Preparation Products

Tosyl cyanideSupplier

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