142662

Chlorosulfonyl isocyanate

98%

• Synonym(s): N-Carbonylsulfamyl chloride, CSI
• Linear Formula: ClSO₂NCO
• CAS Number: 1189-71-5
• Molecular Weight: 141.53
• Beilstein: 1237247
• EC Number: 214-715-2
• MDL number: MFCD00011608
• UNSPSC Code: 12352100
• PubChem Substance ID: 24848531
• NACRES: NA.22

Properties

• vapor pressure: 5.57 psi ( 20 °C)
• Quality Level: 200
• Assay: 98%
• form: liquid
• refractive index: n20/D 1.447 (lit.)
• bp: 107 °C (lit.)
• mp: −44 °C (lit.)
• density: 1.626 g/mL at 25 °C (lit.)
• storage temp.: 2-8°C
• SMILES string: ClS(=O)(=O)N=C=O
• InChI: 1S/CClNO3S/c2-7(5,6)3-1-4
• InChI key: WRJWRGBVPUUDLA-UHFFFAOYSA-N
• Gene Information: human ... ABCB1(5243) , FPR1(2357)

Description

General description

Chlorosulfonyl isocyanate is classified as an isocyanate and is widely used as a reagent in sulfonylation and carbamoylation reactions.[1]Chlorosulfonyl isocyanate reacts with hydrocarbon alkenes via stepwise dipolar pathway to give N-chlorosulfonyl-β-lactams[2].

Application

• Chlorosulfonyl isocyanate was used in synthesis and biochemical characterization of new class of membrane-associated glycosyltransferase inhibitors[3].
• It is synthetically versatile reagent[4] and was used in the preparation of amides[5], lactams[6][7] and triazocinones[8].
• It was employed in regio- and diastereoselective introduction of a protected amino group in synthesis of chiral, polyhydroxylated piperidines[9].
• It was used as reagent during the synthesis of novel sulfamides[10].

Employed in a regio- and diastereoselective introduction of a protected amino group in a synthesis of chiral, polyhydroxylated piperidines.[9] Generation of ureas from amino groups in a synthesis of benzimidazolones.[11]

Safety Information

• Pictograms: GHS08,GHS05,GHS07
• Signal Word: Danger
• Hazard Statements: H302,H314,H317,H334
• Precautionary Statements: P261 - P280 - P301 + P312 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Eye Dam. 1 - Resp. Sens. 1 - Skin Corr. 1B - Skin Sens. 1
• Supplementary Hazards: EUH014
• Storage Class Code: 8A - Combustible corrosive hazardous materials
• WGK: WGK 3
• Flash Point(F): >230.0 °F
• Flash Point(C): > 110 °C
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves