Oxalyl Chloride

Other Names:

Ethanedioyl dichloride

General Information:

Structure:

CAS Number: 79-37-8

Molecular Weight: 126.93 g/mol

Appearance: Colorless liquid

Melting Point: -12 C

Boiling Point: 63-64 C

Density: 1.48 g/mL

Common Uses:

Reagent for the conversion of carboxylic acids to acid chlorides

Procedure excerpt:

To a suspension of the SM (0.3 g, 2.38 mmol) in DCM (10 mL) was added (COCl)2 (0.3 mL, 3.6 mmol) dropwise at 0 C. The resulting mixture was stirred at RT for 1 h then . . .

[full procedure]

Reagent in the conversion of primary alcohols to adehydes via Swern oxidation

Procedure excerpt:

To a solution of (COCl)2 (19.0 g, 0.15 mol) in dry DCM (180 mL) was added dropwise a solution of dry DMSO (22.0 g, 0.30 mol) in dry DCM (60 mL) at -70 C under N2. The mixture . . .

[full procedure]

Reagent in the conversion of secondary alcohols to ketones via Swern oxidation

Procedure excerpt:

. . . solution of (COCl)2 (0.49 mL, 5.5 mmol) in DCM (12 mL) was slowly added DMSO (0.79 mL, 11.0 mmol) at -78 C. The resulting mixture was stirred at -78 C for . . .

[full procedure]

Safety:

Oxalyl chloride is very toxic and corrosive. It is severely irritating to eyes, skin, and the respiratory tract. Oxalyl chloride reacts violently with water.

References:

1) Patent Reference: WO2010038081, page 138, (33.8 MB)

2) Patent Reference: WO2010016005, page 120, (11.3 MB)

3) Patent Reference: WO2016011390, page 112, (20.2 MB)

4) Wikipedia: Oxalyl chloride (link)

5) www.sigmaaldrich.com: Oxalyl chloride (link)

6) Pearson, A. J.; Roush, W. R.; Handbook of Reagents for Organic Synthesis; Activating Agents and Protecting Groups