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188204 Aldrich

p-Toluenesulfonylmethyl isocyanide

98%

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

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Properties

Related Categories Building Blocks, Chemical Synthesis, Isocyanides, Nitrogen Compounds, Organic Building Blocks More...
InChI Key   CFOAUYCPAUGDFF-UHFFFAOYSA-N
assay   98%
mp   109-113 °C(lit.)
solubility   water: slightly soluble
storage temp.   2-8°C

Description

Packaging

5, 25 g in glass bottle

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

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.

Safety & Documentation

Safety Information

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

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Protocols & Articles
Peer-Reviewed Papers
15

References

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