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O8801

Sigma-Aldrich

Oxalyl chloride

reagent grade, 98%

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Synonym(s):
Ethanedioyl dichloride
Linear Formula:
ClCOCOCl
CAS Number:
Molecular Weight:
126.93
Beilstein/REAXYS Number:
1361988
EC Number:
MDL number:
PubChem Substance ID:

grade

reagent grade

Quality Level

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

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1 of 4

This Item
2210151577678.07066
Oxalyl chloride reagent grade, 98%

O8801

Oxalyl chloride

Oxalyl chloride ReagentPlus®, ≥99%

221015

Oxalyl chloride

Sulfuryl chloride 97%

157767

Sulfuryl chloride

Oxalyl chloride for synthesis

8.07066

Oxalyl chloride

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

reaction suitability

reagent type: oxidant

reaction suitability

reagent type: oxidant

reaction suitability

-

reaction suitability

-

bp

62-65 °C (lit.)

bp

62-65 °C (lit.)

bp

68-70 °C (lit.)

bp

63-64 °C/1013 hPa

density

1.5 g/mL at 20 °C (lit.)

density

1.5 g/mL at 20 °C (lit.)

density

1.665 g/mL at 20 °C (lit.)

density

1.48 g/cm3 at 20 °C

mp

−10-−8 °C (lit.)

mp

−10-−8 °C (lit.)

mp

−54 °C (lit.)

mp

-12 °C

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

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Dam. 1 - Skin Corr. 1B - Water-react 1

Storage Class

4.3 - Hazardous materials, which set free flammable gases upon contact with water

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Faceshields, Gloves, Goggles


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Oxalyl chloride as a practical carbon monoxide source for carbonylation reactions.
Hansen SVF and Ulven T.
Organic Letters, 17(11), 2832-2835 (2015)
A direct access to α-diones from oxalyl chloride.
Babudri F, et al.
Tetrahedron Letters, 36(40), 7305-7308 (1995)
Systematic survey of positive chlorine sources in the asymmetric Appel reaction: oxalyl chloride as a new phosphine activator.
Rajendran KV, et al.
Tetrahedron Letters, 54(51), 7009-7012 (2013)
Oxalyl halides: Part II. Vibrational spectra and assignments for oxalyl fluoride and oxalyl chloride fluoride.
Hencher JL and King GW.
Journal of Molecular Spectroscopy, 16(1), 168-178 (1965)
Taisuke Itaya et al.
Chemical & pharmaceutical bulletin, 50(1), 83-86 (2002-02-05)
The relationship between the product patterns and the configurations of 1,2-cycloheptane- and 1,2-cyclooctanediols 9 in the cyclocondensations with oxalyl chloride in the presence of triethylamine at 0 degrees C has been shown analogous to that obtained for 1,2-disubstituted acyclic ethylene

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