188204

Sigma-Aldrich

p-Toluenesulfonylmethyl isocyanide

98%

Synonym(s):
TosMIC, Tosylmethyl isocyanide, (p-Tolylsulfonyl)methyl isocyanide
Linear Formula:
CH3C6H4SO2CH2NC
CAS Number:
Molecular Weight:
195.24
Beilstein/REAXYS Number:
3592382
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

98%

mp

109-113 °C (lit.)

solubility

water: slightly soluble

storage temp.

2-8°C

SMILES string

Cc1ccc(cc1)S(=O)(=O)CN+#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

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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

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Supp Hazards

EUH032

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

T

Risk Statement

23/24/25

Safety Statement

36/37-45

RIDADR

UN 2811 6.1 / PGIII

WGK Germany

WGK 3

Tetrahedron Letters, 48, 5977-5977 (2006)
Il Farmaco (Societa Chimica Italiana : 1989), 48, 209-209 (1993)
Kang Wang et al.
Science advances, 5(6), eaaw2953-eaaw2953 (2019-06-20)
Organic solid-state lasers are essential for various photonic applications, yet current-driven lasing remains a great challenge. Charge transfer (CT) complexes formed with p-/n-type organic semiconductors show great potential in electrically pumped lasers, but it is still difficult to achieve population...
Swapan K Samanta et al.
Bioorganic & medicinal chemistry letters, 15(16), 3717-3719 (2005-07-05)
A convenient method for the synthesis of 1,5-disubstituted imidazoles has been developed on a polymeric support using base-promoted 1,3-dipolar cycloaddition reaction of p-toluenesulfonylmethyl isocyanide (TOSMIC) with immobilized imines under microwave irradiation. The immobilized imines were synthesized by the reaction of...
Hiroshi Nagase et al.
Bioorganic & medicinal chemistry letters, 21(20), 6198-6202 (2011-09-06)
An improved synthetic method for triplet drugs with the 1,3,5-trioxazatriquinane skeleton was developed that used p-toluenesulfonylmethyl isocyanide (TosMIC) instead of 1,3-dithiane. Using the improved method, we synthesized compounds with two identical pharmacophore units and an epoxymethano group, that is, capped...

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