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571024

Sigma-Aldrich

Chlorosulfonic acid

99%

Synonym(s):

Sulfuric chlorohydrin

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About This Item

Linear Formula:
ClSO3H
CAS Number:
Molecular Weight:
116.52
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.21

vapor density

4 (vs air)

Quality Level

vapor pressure

1 mmHg ( 25 °C)
3.3 mmHg ( 37.7 °C)

assay

99%

expl. lim.

37.7 %

refractive index

n20/D 1.433 (lit.)

bp

151-152 °C/755 mmHg (lit.)

solubility

acetic acid: soluble(lit.)
chloroform: soluble(lit.)
dichloromethane: soluble(lit.)

density

1.753 g/mL at 25 °C (lit.)

SMILES string

OS(Cl)(=O)=O

InChI

1S/ClHO3S/c1-5(2,3)4/h(H,2,3,4)

InChI key

XTHPWXDJESJLNJ-UHFFFAOYSA-N

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General description

Chlorosulfonic acid is a strong acid that is synthesized on an industrial scale by reacting sulfur trioxide and dry hydrogen chloride gas in an equimolar ratio. It can act as a sulfonating, dehydrating, oxidizing and chlorinating agent. It is reported to be a better electrophilic olefin cyclization agent in comparison to other sulfonic acids. Its infrared spectra in the solid, liquid and gaseous state have been recorded in the region 4000-400cm-1.

Application

Chlorosulfonic acid may be used in the following processes:
  • Synthesis of di-n-butyl ammonium chlorosulfonate, a secondary amine ionic liquid.
  • To prepare sulfonated polyethersulfone (SPES) with enhanced hydrophilic property.
  • To attach sulfate group to silk fibroin for improving its anticoagulant ability.
  • As a catalyst to prepare substituted coumarin, via von Pechmann condensation between phenol and β-ketoester.
  • As a substitute to acid catalyst in Biginelli reaction to prepare 3,4dihydropyrimidines.

pictograms

Skull and crossbonesCorrosion

signalword

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Eye Dam. 1 - Skin Corr. 1A - STOT SE 3

target_organs

Respiratory system

supp_hazards

Storage Class

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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


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Chlorosulfonic acid as a convenient electrophilic olefin cyclization agent.
Linares-Palomino PJ, et al.
Tetrahedron Letters, 44(35), 6651-6655 (2003)
Infrared spectra of methane-, fluoro-, and chlorosulfonic acids.
Chackalackal SM and Stafford FE.
Journal of the American Chemical Society, 88(21), 4815-4819 (1966)
Chlorosulfonic acid-catalysed one-pot synthesis of coumarin.
Kotharkar SA, et al.
Mendeleev Communications, 16(4), 241-242 (2006)
Chlorosulfonic acid catalyzed highly efficient solvent-free synthesis of 3,4-Dihydropyrimidin-2(1H)-one and thiones.
Kotharkar SA, et al.
Ukrainica Bioorganica Acta, 2, 17-21 (2006)
Polyethersulfone sulfonated by chlorosulfonic acid and its membrane characteristics.
Guan R, et al.
European Polymer Journal, 41(7), 1554-1560 (2005)

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