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Sigma-Aldrich

Chlorocarbonylsulfenyl chloride

96%

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Synonym(s):
(Chlorothio)formyl chloride, Chloroformylsulfenyl chloride
Linear Formula:
ClCOSCl
CAS Number:
2757-23-5
Molecular Weight:
130.98
Beilstein:
506318
EC Number:
220-415-2
MDL number:
MFCD00000703
PubChem Substance ID:
24854852
NACRES:
NA.22

Quality Level

100

Assay

96%

form

liquid

refractive index

n20/D 1.517 (lit.)

bp

98 °C (lit.)

density

1.552 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

ClSC(Cl)=O

InChI

1S/CCl2OS/c2-1(4)5-3

InChI key

MNOALXGAYUJNKX-UHFFFAOYSA-N

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Application

Chlorocarbonylsulfenyl chloride has been used in the preparation of:
  • 5-(1,2,3,4-tetra-O-acetyl-alpha-D-xylopyranos-5S-C-yl)-1,3,4-oxathiazol-2-one
  • fluorinated oxathialones
  • polyfluoroalkylchlorothioformates
  • chlorocarbonylpolyfluoroalkylsulfenate esters
  • chlorocarbonylhexafluoroisopropylidenimino sulfenate
  • 5-tri-fluoromethyl-2-oxo-1,3,4-oxathiazole
  • commercially important N,N-dialkylcarbamoyl chlorides

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible, corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

143.6 °F - closed cup

Flash Point(C)

62 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Some fluorinated heterocyclic and acyclic derivatives of chlorocarbonylsulfenyl chloride.
John EO and Jean'ne MS.
Journal of Fluorine Chemistry, 36(4), 429-438 (1987)
Keith G McMillan et al.
Carbohydrate research, 341(1), 41-48 (2005-11-03)
5-(1,2,3,4-tetra-O-acetyl-alpha-D-xylopyranos-5S-C-yl)-1,3,4-oxathiazol-2-one (8) has been prepared from glucuronamide in two steps and 73% overall yield by conversion to the tetra-O-acetyl derivative 7 followed by reaction with chlorocarbonylsulfenyl chloride. 5-(2,3,4-Tri-O-acetyl-beta-D-xylopyranosyl)-1,3,4-oxathiazol-2-one (12) was synthesised from D-xylose by a four-step sequence involving conversion to
An improved one-pot cost-effective synthesis of N, N-disubstituted carbamoyl halides and derivatives.
Adeppa K, et al.
Canadian Journal of Chemistry, 88(!2), 1277-1280 (2010)

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