Key Documents

View All Documentation

O8801

Oxalyl chloride

Name: Oxalyl chloride
Brand: ALDRICH

reagent grade, 98%

Synonym(s):

Ethanedioyl dichloride

Select a Size

Change View

About This Item

Linear Formula:

ClCOCOCl

CAS Number:

79-37-8

Molecular Weight:

126.93

UNSPSC Code:

12352106

NACRES:

NA.22

PubChem Substance ID:

57654494

EC Number:

201-200-2

Beilstein/REAXYS Number:

1361988

MDL number:

MFCD00000704

Assay:

98%

Technical Service

Need help? Our team of experienced scientists is here for you.

Let Us Assist

Properties

grade

reagent grade

Quality Level

200

vapor density

4.4 (vs air)

vapor pressure

150 mmHg ( 20 °C)

assay

98%

reaction suitability

reagent type: oxidant

impurities

≤1.0% phosgene content

refractive index

n20/D 1.429 (lit.)

bp

62-65 °C (lit.)

mp

−10-−8 °C (lit.)

density

1.5 g/mL at 20 °C (lit.)

SMILES string

ClC(=O)C(Cl)=O

InChI

1S/C2Cl2O2/c3-1(5)2(4)6

InChI key

CTSLXHKWHWQRSH-UHFFFAOYSA-N

Description

General description

Oxalyl chloride is a versatile reagent in various chemical transformations, such as chlorination, dichlorination, oxidation, reduction, dehydration, decarboxylation, formylation, and ring cleavage of epoxides.

Application

Oxalyl chloride can be used as an oxidizing agent:

To synthesize β, β′-diketodithioethers from β, β′-dihydroxydithioethers via Swern oxidation.
In the DMSO-catalyzed Swern oxidation of primary amides or aldoximes to nitriles in the presence of triethylamine as a base.
In the Moffatt-Swern oxidation of aryl allylic alcohols to halogenated unsaturated ketones in the presence of triethylamine.

Reactant involved in:

Synthesis of N-heterocyclic ynones and ynediones, used to activate carboxylic acids
Chlorination and halogenation
Three-component [3+2] cycloadditions
Reactions with organostannanes
Synthesis of cyclopentenones
Carbonylations, used as a carbonyl synthon