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691399

Sigma-Aldrich

Chlorosulfonyl isocyanate

Arxada quality, 99.0-100.3 % (w/w) (T)

Synonym(s):

N-Carbonylsulfamyl chloride, CSI

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About This Item

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:
329761405
NACRES:
NA.22

vapor pressure

5.57 psi ( 20 °C)

form

liquid

quality

Arxada quality

manufacturer/tradename

Arxada AG

concentration

99.0-100.3 % (w/w) (T)

impurities

≤1.00% chloropropylsulfonyl isocyanate

refractive index

n20/D 1.447 (lit.)

bp

107 °C (lit.)

mp

−44 °C (lit.)

density

1.626 g/mL at 25 °C (lit.)

SMILES string

ClS(=O)(=O)N=C=O

InChI

1S/CClNO3S/c2-7(5,6)3-1-4

InChI key

WRJWRGBVPUUDLA-UHFFFAOYSA-N

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Application

  • Pharmaceutical intermediates: A study explored the synthesis and carbonic anhydrase inhibitory properties of sulfamides derived from Chlorosulfonyl isocyanate, demonstrating its potential in the development of new therapeutic agents, particularly for treating conditions involving carbonic anhydrase enzymes (Aksu et al., 2013).
  • Stereochemical synthesis applications: Chlorosulfonyl isocyanate was utilized for the stereoselective amination of chiral benzylic ethers in the total synthesis of (+)-sertraline, showcasing its critical role in the precise construction of complex pharmaceuticals (Lee et al., 2011).
  • One-pot synthetic transformations: The compound′s use in one-pot conversion of trimethylsilyl ethers into urethanes was highlighted, further applied to synthesize novel neuromodulators like carisbamate. This illustrates Chlorosulfonyl isocyanate′s versatility in facilitating efficient and innovative synthetic routes in medicinal chemistry (Dong et al., 2008).

Signal Word

Danger

Hazard Statements

H302,H314,H317,H334

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J A Picard et al.
Journal of medicinal chemistry, 39(6), 1243-1252 (1996-03-15)
Several series of acyl-CoA:cholesterol O-acyltransferase inhibitors were prepared by the stepwise addition of nitrogen, oxygen, and sulfur nucleophiles to N-chlorosulfonyl isocyanate. The (aminosulfonyl)ureas 3-44 were the most potent inhibitors in vitro, with several compounds having IC50 values < 1 microM.
C P Sharma et al.
Biomaterials, medical devices, and artificial organs, 12(3-4), 215-233 (1984-01-01)
Natural rubber with C = C bonds had been modified by reaction with chlorosulfonyl isocyanate (CSI) and 70% of the products were obtained, which yielded polyelectrolyte on treatment with NaOH, having sulfamate and carboxylate groups. The polyelectrolyte showed anticoagulant activity.
G Crassous et al.
Biomaterials, 5(3), 153-156 (1984-05-01)
In this paper we report the preparation of a new asymmetric semipermeable styrene-isoprene-styrene block-copolymer membrane. Its modification by addition of gaseous N-chlorosulphonylisocyanate alters neither its permselectivity nor its water permeability rate. This modified membrane possesses an antithrombic activity which depends

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