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320536

Sigma-Aldrich

Thionyl chloride

reagent grade, 97%

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Linear Formula:
SOCl2
CAS Number:
Molecular Weight:
118.97
Beilstein/REAXYS Number:
1209273
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

grade

reagent grade

Quality Level

vapor pressure

97 mmHg ( 20 °C)

assay

97%

form

liquid

refractive index

n20/D 1.518 (lit.)

bp

79 °C (lit.)

mp

−105 °C (lit.)

density

1.631 g/mL at 25 °C (lit.)

SMILES string

ClS(Cl)=O

InChI

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

InChI key

FYSNRJHAOHDILO-UHFFFAOYSA-N

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This Item
2304644472858.08154
vibrant-m

320536

Thionyl chloride

vibrant-m

230464

Thionyl chloride

vibrant-m

447285

Thionyl chloride

vibrant-m

8.08154

Thionyl chloride

form

liquid

form

liquid

form

liquid

form

liquid

assay

97%

assay

≥99%

assay

99.5%

assay

-

vapor pressure

97 mmHg ( 20 °C)

vapor pressure

97 mmHg ( 20 °C)

vapor pressure

97 mmHg ( 20 °C)

vapor pressure

121 hPa ( 20 °C)

mp

−105 °C (lit.)

mp

−105 °C (lit.)

mp

−105 °C (lit.)

mp

-104.5 °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.)

density

1.64 g/cm3 at 20 °C

General description

Thionyl chloride is an inorganic acid chloride mainly used as a reagent to prepare carboxylic acid chlorides from carboxylic acids.

Application

Thionyl chloride may be used in the following processes:
  • To facilitate the synthesis of indenones from 3-hydroxyindanones via dehydroxylation.
  • To functionalize silica gel for thioacetalization of aldehydes.
  • Conversion of tert-butyl esters to acid chlorides.
  • Conversion of aliphatic and aromatic sulfoxides to sulfides in the presence of triphenylphosphine.

pictograms

CorrosionSkull and crossbones

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

supp_hazards

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

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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Organic Chemistry, 607-607 null
The Conversion of tert-Butyl Esters to Acid Chlorides Using Thionyl Chloride.
Greenberg JA & Sammakia T
The Journal of Organic Chemistry, 82(6), 3245-3251 (2017)
Deoxygenation of sulfoxides to sulfides with thionyl chloride and triphenylphosphine: Competition with the Pummerer reaction
Jang Y, et al.
The Journal of Organic Chemistry, 78(12), 6328-6331 (2013)
Mojtaba Taseidifar
Ecotoxicology and environmental safety, 206, 111389-111389 (2020-09-29)
An improved method has been developed for the efficient synthesis of octanoyl-cysteine in single-chain form (N-octanoyl-cys) which operates as a surfactant over a wide pH range, is easily decomposed into natural products and has a high product yield. The compound
Selective protection of carbonyl compounds. Silica gel treated with thionyl chloride as an effective catalyst for thioacetalization.
Kamitori Y, et al.
The Journal of Organic Chemistry, 51(9), 1427-1431 (1986)

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