188204

p-Toluenesulfonylmethyl isocyanide

98%

• Synonym(s): (p-Tolylsulfonyl)methyl isocyanide, TosMIC, Tosylmethyl isocyanide
• Linear Formula: CH₃C₆H₄SO₂CH₂NC
• CAS Number: 36635-61-7
• Molecular Weight: 195.24
• Beilstein: 3592382
• EC Number: 253-140-1
• MDL number: MFCD00000005
• UNSPSC Code: 12352100
• PubChem Substance ID: 24851306
• NACRES: NA.22

Properties

• Assay: 98%
• form: solid
• 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

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H300 + H310 + H330
• Precautionary Statements: P260 - P262 - P264 - P280 - P302 + P352 + P310 - P304 + P340 + P310
• Hazard Classifications: Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral
• Supplementary Hazards: EUH032
• Storage Class Code: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves