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Merck
모든 사진(2)

주요 문서

188204

Sigma-Aldrich

p-Toluenesulfonylmethyl isocyanide

98%

동의어(들):

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

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About This Item

Linear Formula:
CH3C6H4SO2CH2NC
CAS Number:
Molecular Weight:
195.24
Beilstein:
3592382
EC Number:
MDL number:
UNSPSC 코드:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

분석

98%

형태

solid

mp

109-113 °C (lit.)

solubility

water: slightly soluble

작용기

amine
isonitrile
sulfone

저장 온도

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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일반 설명

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.

애플리케이션

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

픽토그램

Skull and crossbones

신호어

Danger

유해 및 위험 성명서

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

보충제 위험성

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

개인 보호 장비

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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문서 라이브러리 방문

이미 열람한 고객

Tetrahedron Letters, 48, 5977-5977 (2006)
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
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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