Chlorosulfonyl isocyanate, CAS No. 1189-71-5

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1189-71-5

Catalog No. EBD8603

CAS 1189-71-5

Name Chlorosulfonyl isocyanate

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Basic Information

Synonyms: carbonylsulfamoylchloride sulfurylchlorideisocyanate chlorosulfonylisocyanate(csi) chlorosulphonylisocyanate chlorosulfonyllsocyanate chlorosulfonylisocyanate,98+% N-Carbonylsulfamylchloride CSI Chlorosulfonylisocyanate sulfurisocyanatidoylchloride

Molecular Formula: CClNO3S

Molecular Weight: 141.53

MDL Number: MFCD00011608

Categories: Synthetic Chemistry > Basic Synthetic Reagents > Halogenation Reagents Synthetic Chemistry > Organic Building Blocks > Phosphorus Compounds

Product Description:

Chlorosulfonyl isocyanate (CSI, CAS 1189-71-5) is a highly reactive, colorless to pale yellow liquid with a pungent odor. It is a versatile reagent characterized by the presence of both a sulfonyl chloride and an isocyanate functional group. Its molecular formula is ClSO₂NCO. Its primary application is as a powerful chlorosulfonylation and cycloaddition reagent in organic synthesis. It is extensively used for the synthesis of heterocyclic compounds, particularly β-lactams (azetidin-2-ones), which are core structures in many antibiotics. CSI readily undergoes [2+2] cycloaddition reactions with alkenes to form these four-membered rings. Furthermore, it serves as a key reagent for introducing the chlorosulfonyl group, a precursor to sulfonamides and other sulfur-containing functionalities. Due to its extreme reactivity with moisture and its toxicity (corrosive, lachrymator), it must be handled with stringent precautions under anhydrous conditions in a well-ventilated fume hood. It is a valuable but specialized tool in medicinal chemistry and fine chemical synthesis for constructing complex molecular architectures.

Physical Properties

Melting Point: −44 °C(lit.)

Boiling Point: 107 °C(lit.)

Flash Point: 18.5 °C

Density: 1.626 g/mL at 25 °C(lit.)

Solubility: reacts violently exothermic

Refractivity: n20/D 1.447(lit.)

Storage: 0-6°C

Safety Information

Packing Level: II

Hazard Category: 8

Transport Codes: 3265

Analytical Data

Appearance: Clear liquid