Thionyl Chloride

Other Names:

Sulfurous oxychloride

Sulfurous dichloride

Thionyl dichloride

General Information:

Structure:

CAS Number: 7719-09-7

Molecular Weight: 118.97 g/mol

Appearance: Clear liquid

Chemical Formula: SOCl2

Melting Point: -105 C

Boiling Point: 79 C

Density: 1.631 g/mL

Common Uses:

Reagent for converting carboxylic acids to acid chlorides

Procedure excerpt:

A mixture of the SM (1.0 g, 6.3 mmol) in ACN (20 mL) was treated with SOCl2 (0.8 mL). The resulting mixture was refluxed for 2 h. The solvent was removed . . .

[full procedure]

Reagent for converting carboxylic acids to esters

Procedure excerpt:

To a solution of the SM (1 g, 3.7 mmol) in MeOH (15 mL) was slowly added SOCl2 (5 mL) at 0 C. The reaction mixture was refluxed at 70 C for 2 h, after which time it was . . .

[full procedure]

Reagent for converting alcohols to chlorides

Procedure excerpt:

To a solution of the SM (294 g, 1.90 mol) in DCM (2.2 L) at -10 C was added SOCl2 (460 g, 3.90 mmol). The reaction mixture was stirred at reflux for 1 h. The mixture was . . .

[full procedure]

Reagent for converting primary amides to nitriles

Procedure excerpt:

A suspension of the SM (10 g, 78 mmol) in SOCl2 (35 mL) was refluxed for 4 h until the suspension became homogenous. The reaction mixture was then cooled . . .

[full procedure]

References:

1) Patent Reference: WO2010016005, page 89, (11.3 MB)

2) Patent Reference: WO2010038081, page 128, (33.8 MB)

3) Patent Reference: WO2016014463, page 91, (6.7 MB)

4) Patent Reference: WO2010104899, page 155, (6.7 MB)

5) Wikipedia: Thionyl chloride (link)

6) www.sigmaaldrich.com: Thionyl chloride (link)