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230464

Sigma-Aldrich

Thionyl chloride

ReagentPlus®, ≥99%

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

Quality Level

vapor pressure

97 mmHg ( 20 °C)

product line

ReagentPlus®

assay

≥99%

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.)

anion traces

chloride (Cl-): 59.0-60.2%

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 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.
  • Surface modification of amorphous carbon nanotubes (α-CNTs) in stearic acid-dichloromethane solution.
  • 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.
  • As an activator to generate ketenes in-situ for preparing 2-azetidinones.

Packaging

5 mL in glass bottle
1, 2.5 L in Sure/Seal™
100, 4×100, 500 mL in Sure/Seal™

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

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

6.1C - 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

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Fox MA and Whitesell JK
Organic Chemistry, 607-607 null
Thionyl chloride (or oxalyl chloride) as an efficient acid activator for one-pot synthesis of [Beta]-lactams.
Ebrahimi E & Jarrahpour A.
Iranian Journal of Science and Technology, 38(A1), 49-49 (2014)
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)
Thionyl chloride assisted functionalization of amorphous carbon nanotubes: A better field emitter and stable nanofluid with better thermal conductivity.
Sarkar SK, et al.
Mat. Res. Bul., 1-8 (2015)

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