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320536

Sigma-Aldrich

Thionyl chloride

reagent grade, 97%

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

Quality Level

grade

reagent grade

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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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.

Packaging

1 L in Sure/Seal™

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Supplementary Hazards

Storage Class Code

8A - Combustible, corrosive 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

Certificate of Analysis

Certificate of Origin

Organic Chemistry, 607-607 null
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)
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)
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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