188204
p-Toluenesulfonylmethyl isocyanide
98%
Synonym(s):
(p-Tolylsulfonyl)methyl isocyanide, TosMIC, Tosylmethyl isocyanide
Sign In to View Organizational & Contract Pricing.
Select a Size
Change View
About This Item
Linear Formula:
CH3C6H4SO2CH2NC
CAS Number:
Molecular Weight:
195.24
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
253-140-1
Beilstein/REAXYS Number:
3592382
MDL number:
Assay:
98%
Form:
solid
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
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
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral
supp_hazards
Storage Class
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
ppe
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 188204-25G | 04061838758767 |
| 188204-5G | 04061838758774 |