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188204 Sigma-Aldrich

p-Toluenesulfonylmethyl isocyanide

98%

Synonym: (p-Tolylsulfonyl)methyl isocyanide, TosMIC, Tosylmethyl isocyanide

  • CAS Number 36635-61-7

  • Linear Formula CH3C6H4SO2CH2NC

  • Molecular Weight 195.24

  •  Beilstein/REAXYS Number 3592382

  •  EC Number 253-140-1

  •  MDL number MFCD00000005

  •  PubChem Substance ID 24851306

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, Chemical Synthesis, Isocyanides, Nitrogen Compounds - Organic Building Blocks, Organic Building Blocks More...
Quality Level   200
assay   98%
mp   109-113 °C (lit.)
solubility   water: slightly soluble
storage temp.   2-8°C
SMILES string   Cc1ccc(cc1)S(=O)(=O)C[N+]#[C-]
InChI   1S/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3
InChI key   CFOAUYCPAUGDFF-UHFFFAOYSA-N

Description

General description

p-Toluenesulfonylmethyl isocyanide undergoes base-promoted 1,3-dipolar cycloaddition reaction with immobilized imines under microwave irradiation to yield 1,5-disubstituted imidazoles. It is a versatile synthon in organic chemistry, extensively used for the synthesis of heterocyclic compounds.

Application

p-Toluenesulfonylmethyl isocyanide was used:
• in the synthesis of triplet drugs with the 1,3,5-trioxazatriquinane skeleton
• as reagent in the preparation of biologically active pyrroles and imidazoles
• as the isonitrile component in a diastereoselective Passerini reaction employing sugar-derived aldehydes

Packaging

5, 25 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Supplemental Hazard Statements 
EUH032
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
WGK 3

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Protocols & Articles
Peer-Reviewed Papers
15

References

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