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188204

Sigma-Aldrich

p-Toluenesulfonylmethyl isocyanide

98%

Synonym(s):

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

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About This Item

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

Assay

98%

form

solid

mp

109-113 °C (lit.)

solubility

water: slightly soluble

functional group

amine
isonitrile
sulfone

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

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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

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310 + H330

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ9687
BCCL1416
BCCH0072
BCCF8293
BCCF0553

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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
p-Toluenesulfonylmethyl Isocyanide: A Versatile Synthon in Organic Chemistry.
Tandon VK and Rai S.
Journal of Sulfur Chemistry, 24(3), 307-385 (2003)
Tetrahedron Letters, 48, 5977-5977 (2006)
Il Farmaco (Societa Chimica Italiana : 1989), 48, 209-209 (1993)
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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