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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

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Supplementary Hazards

Storage Class Code

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

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

EU REACH Annex XVII (Restriction List)

CAS No.

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Certificates of Analysis (COA)

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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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