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Sigma-Aldrich

p-Toluenesulfonylmethyl isocyanide

98%

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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

Quality Level

200

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

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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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Il Farmaco (Societa Chimica Italiana : 1989), 48, 209-209 (1993)
p-Toluenesulfonylmethyl Isocyanide: A Versatile Synthon in Organic Chemistry.
Tandon VK and Rai S.
Journal of Sulfur Chemistry, 24(3), 307-385 (2003)
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
Tetrahedron Letters, 48, 5977-5977 (2006)
Medicinal Chemistry Research, 3, 192-192 (1993)
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