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8.08154

Sigma-Aldrich

Thionyl chloride

for synthesis

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Synonym(s):
Thionyl chloride, Sulfurous acid dichloride, Sulfurous oxychloride
Empirical Formula (Hill Notation):
Cl2OS
CAS Number:
Molecular Weight:
118.97
MDL number:
EC Index Number:
231-748-8

vapor pressure

121 hPa ( 20 °C)

Quality Level

form

liquid

potency

324 mg/kg LD50, oral (Rat)

bp

76 °C/1013 hPa

mp

-104.5 °C

density

1.64 g/cm3 at 20 °C

storage temp.

2-30°C

InChI

1S/Cl2OS/c1-4(2)3

InChI key

FYSNRJHAOHDILO-UHFFFAOYSA-N

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This Item
230464320536447285
Thionyl chloride for synthesis

Sigma-Aldrich

8.08154

Thionyl chloride

Thionyl chloride ReagentPlus®, ≥99%

Sigma-Aldrich

230464

Thionyl chloride

Thionyl chloride reagent grade, 97%

Sigma-Aldrich

320536

Thionyl chloride

Thionyl chloride ReagentPlus®, 99.5%, low iron

Sigma-Aldrich

447285

Thionyl chloride

form

liquid

form

liquid

form

liquid

form

liquid

mp

-104.5 °C

mp

−105 °C (lit.)

mp

−105 °C (lit.)

mp

−105 °C (lit.)

density

1.64 g/cm3 at 20 °C

density

1.631 g/mL at 25 °C (lit.)

density

1.631 g/mL at 25 °C (lit.)

density

1.631 g/mL at 25 °C (lit.)

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

potency

324 mg/kg LD50, oral (Rat)

potency

-

potency

-

potency

-

General description

Thionyl chloride is an inorganic acid chloride. It is mainly used as a chlorinating agent in organic synthesis for the production of organochlorine compounds.

Application

Thionyl chloride can be used as a catalyst to synthesize:
  • 4-(sulfinylamino)-1,2,4-triazole by reacting with 4-amino-1,2,4-triazole.
  • Isothiazolopyrimidines from aminouracils via cyclization reaction.
  • 1,2,6-triazine S-oxides by reacting with diimines via condensation reactions in the presence of pyridine.
  • 2-oxo-1,3,2-dioxathianes by condensation reaction with alkane-1,3-diols.
  • Cyclic sulfites by reacting with nitroglycols.
  • Microporous organic polymers by aldol self-condensation reaction of di and multiacetyl building blocks.

Analysis Note

Assay (argentometric): ≥ 99.0 %
Identity (IR): passes test

Pictograms

CorrosionSkull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1A - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

Storage Class Code

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Synthetic uses of thionyl chloride
El-Sakka IA and Hassan NA
Journal of Sulfur Chemistry, 26(1), 33-97 (2005)
Thionyl chloride-catalyzed preparation of microporous organic polymers through aldol condensation
Zhao Yan-Chao, et al.
Macromolecules, 44(16), 6382-6388 (2011)

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