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142662

Sigma-Aldrich

Chlorosulfonyl isocyanate

98%

Synonyme(s) :

CSI

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About This Item

Formule linéaire :
ClSO2NCO
Numéro CAS:
1189-71-5
Poids moléculaire :
141.53
Numéro Beilstein :
1237247
Numéro CE :
214-715-2
Numéro MDL:
MFCD00011608
Code UNSPSC :
12352100
ID de substance PubChem :
24848531
Nomenclature NACRES :
NA.22

Pression de vapeur

5.57 psi ( 20 °C)

Niveau de qualité

200

Pureté

98%

Forme

liquid

Indice de réfraction

n20/D 1.447 (lit.)

Point d'ébullition

107 °C (lit.)

Pf

−44 °C (lit.)

Densité

1.626 g/mL at 25 °C (lit.)

Température de stockage

2-8°C

Chaîne SMILES 

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

InChI

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

Clé InChI

WRJWRGBVPUUDLA-UHFFFAOYSA-N

Informations sur le gène

human ... ABCB1(5243) , FPR1(2357)

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Description générale

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.

Pictogrammes

Health hazardCorrosionExclamation mark
GHS08,GHS05,GHS07

Mention d'avertissement

Danger

Mentions de danger

H302,H314,H317,H334

Classification des risques

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

Risques supp

EUH014

Code de la classe de stockage

8A - Combustible corrosive hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

>230.0 °F

Point d'éclair (°C)

> 110 °C

Équipement de protection individuelle

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificats d'analyse (COA)

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Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

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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.
Synthetic Communications, 22, 2729-2729 (1992)
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
Synlett, 539-539 (1994)
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
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