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248835 Sigma-Aldrich

p-Toluenesulfonyl cyanide

technical grade, 95%

Synonym: p-Tolylsulfonyl cyanide, Tosyl cyanide

  • CAS Number 19158-51-1

  • Linear Formula CH3C6H4SO2CN

  • Molecular Weight 181.21

  •  Beilstein/REAXYS Number 2048159

  •  EC Number 242-849-1

  •  MDL number MFCD00009977

  •  PubChem Substance ID 24854953

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, C8 to C9, Chemical Synthesis, Cyanides/Nitriles, Nitrogen Compounds - Organic Building Blocks,
Quality Level   100
grade   technical grade
assay   95%
bp   105-106 °C/1 mmHg (lit.)
mp   47-50 °C (lit.)
storage temp.   2-8°C
SMILES string   Cc1ccc(cc1)S(=O)(=O)C#N
InChI   1S/C8H7NO2S/c1-7-2-4-8(5-3-7)12(10,11)6-9/h2-5H,1H3
InChI key   JONIMGVUGJVFQD-UHFFFAOYSA-N

Description

General description

p-Toluenesulfonyl cyanide is an electron-deficient nitrile and undergoes hetero-Diels-Alder reaction with the silyl enol ether of cyclohexenone to yield hydrolytically sensitive [4+2] adduct. It undergoes facile [2+3] cycloaddition reaction with azides to form 5-sulfonyl tetrazoles. It 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.

Application

p-Toluenesulfonyl cyanide has been used in:
• the preparation of polyfunctional nitriles
• free-radical cyanation of B-alkylcatecholboranes

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 3261 8 / PGII
WGK Germany 
WGK 3
Flash Point(F) 
230.0 °F - closed cup
Flash Point(C) 
110 °C - closed cup

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Protocols & Articles
Peer-Reviewed Papers
15

References

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