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Merck
CN

142662

Chlorosulfonyl isocyanate

98%

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24848531
EC Number:
214-715-2
Beilstein/REAXYS Number:
1237247
MDL number:
MFCD00011608

Key Documents

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Product Name

Chlorosulfonyl isocyanate, 98%

InChI key

WRJWRGBVPUUDLA-UHFFFAOYSA-N

InChI

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

SMILES string

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

vapor pressure

5.57 psi ( 20 °C)

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

Quality Level

200

Gene Information

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

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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.

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.

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Danger

Hazard Classifications

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

supp_hazards

EUH014

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

>230.0 °F

flash_point_c

> 110 °C

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB4145
STBK1563
STBJ9968
0000099574
0000099571

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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
Synthesis and antibacterial activity of sulfonamides. SAR and DFT studies
Boufas, Wahida et al.
Journal of Molecular Structure, 180-185 (2014)
Synthetic Communications, 22, 2729-2729 (1992)
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, 23, 2151-2151 (1993)
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Protocols

UHPLC/MS for Drug Detection in Urine

Optimize β-glucuronidase hydrolysis for glucuronide metabolite analysis considering factors like time, temperature, pH, and enzyme concentration.

使用UHPLC/MS（TOF）检测不同酶水解条件处理的尿液中药物和代谢物

为了使用β-葡糖醛酸酶优化水解，必须对每种待分析的葡糖苷酸代谢物进行某些因素的评估，例如孵育时间、温度、水解pH、酶源和酶浓度。

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