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Sigma-Aldrich

Chlorosulfonyl isocyanate

98%

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Synonym(s):
N-Carbonylsulfamyl chloride, CSI
Linear Formula:
ClSO2NCO
CAS Number:
Molecular Weight:
141.53
Beilstein:
1237247
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

vapor pressure

5.57 psi ( 20 °C)

Quality Level

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

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1 of 4

This Item
217328691399317438
form

liquid

form

-

form

liquid

form

-

refractive index

n20/D 1.447 (lit.)

refractive index

n20/D 1.480 (lit.)

refractive index

n20/D 1.447 (lit.)

refractive index

-

bp

107 °C (lit.)

bp

80-85 °C/20 mmHg (lit.)

bp

107 °C (lit.)

bp

130 °C/1 mmHg (lit.)

mp

−44 °C (lit.)

mp

-

mp

−44 °C (lit.)

mp

55-58 °C (lit.)

density

1.626 g/mL at 25 °C (lit.)

density

1.581 g/mL at 25 °C (lit.)

density

1.626 g/mL at 25 °C (lit.)

density

-

General description

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

Application

  • Chlorosulfonyl isocyanate was used in synthesis and biochemical characterization of new class of membrane-associated glycosyltransferase inhibitors.
  • It is synthetically versatile reagent and was used in the preparation of amides, lactams and triazocinones.
  • It was employed in regio- and diastereoselective introduction of a protected amino group in synthesis of chiral, polyhydroxylated piperidines.
  • It was used as reagent during the synthesis of novel sulfamides.
Employed in a regio- and diastereoselective introduction of a protected amino group in a synthesis of chiral, polyhydroxylated piperidines. Generation of ureas from amino groups in a synthesis of benzimidazolones.

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Resp. Sens. 1 - Skin Corr. 1B - Skin Sens. 1

Supplementary Hazards

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

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P Paul et al.
The Journal of biological chemistry, 268(17), 12933-12938 (1993-06-15)
A new class of compounds designed to inhibit membrane-associated glycosyltransferases were synthesized and their biological activities were characterized in liver microsomes and human lymphoma cell lines. These inhibitors are composed of N-acyl phenylaminoalcohol derivatives linked to uridine via different spacers.
Dale F Shellhamer et al.
The Journal of organic chemistry, 78(2), 246-252 (2012-12-15)
Chlorosulfonyl isocyanate (CSI) is reported to react with hydrocarbon alkenes by a stepwise dipolar pathway to give N-chlorosulfonyl-β-lactams that are readily reduced to β-lactams. Substitution of a vinyl hydrogen for a vinyl fluorine changes the dynamics for reaction with CSI
Synthetic Communications, 22, 2729-2729 (1992)
Synthesis and antibacterial activity of sulfonamides. SAR and DFT studies
Boufas, Wahida et al.
Journal of Molecular Structure, 180-185 (2014)
Kadir Aksu et al.
Bioorganic & medicinal chemistry, 21(11), 2925-2931 (2013-04-30)
A series of novel sulfamides incorporating the dopamine scaffold were synthesized. Reaction of amines and tert-butyl-alcohol/benzyl alcohol in the presence of chlorosulfonyl isocyanate (CSI) afforded sulfamoyl carbamates, which were converted to the title compounds by treatment with trifluoroacetic acid or

Protocols

To optimize hydrolysis using β-glucuronidase, factors such as incubation time, temperature, hydrolysis pH, enzyme source, and enzyme concentration must be evaluated for each glucuronide metabolite to be analyzed.

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