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320536

Sigma-Aldrich

Thionyl chloride

reagent grade, 97%

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About This Item

Linear Formula:
SOCl2
CAS Number:
Molecular Weight:
118.97
Beilstein:
1209273
EC Number:
MDL number:
UNSPSC Code:
12352300
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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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

Skull and crossbonesCorrosion

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

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

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.

PDSCL

Deleterious substance

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

320536-VAR:
320536-BULK:
320536-1L:


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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)
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)
Eagleson M.
Concise Encyclopedia Chemistry, 118-118 (1994)

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