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221015

Sigma-Aldrich

Oxalyl chloride

ReagentPlus®, ≥99%

Synonym(s):

Ethanedioyl dichloride

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About This Item

Linear Formula:
ClCOCOCl
CAS Number:
Molecular Weight:
126.93
Beilstein/REAXYS Number:
1361988
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.22

Pricing and availability is not currently available.

vapor density

4.4 (vs air)

Quality Level

vapor pressure

150 mmHg ( 20 °C)

product line

ReagentPlus®

assay

≥99%

form

liquid

reaction suitability

reagent type: oxidant

impurities

<10 ppb Heavy metals

color

APHA: 0-150

refractive index

n20/D 1.429 (lit.)

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General description

Oxalyl chloride is a commonly used chlorinating reagent that can be prepared by the reaction of oxalic acid and phosphorus pentachloride.[1]

application

Oxalyl chloride may be used in the following processes:
  • Preparation of Mosher′s acid chloride by reacting with Mosher′s acid in the presence of DMF.[2]
  • Activation of dimethyl sulfoxide for use in the oxidation of long-chain alcohols to carbonyls.[3]
  • Activation of α-keto carboxylic acids and N-heterocyclic carboxylic acids for alkynylation to form ynediones and N-heterocyclic ynones, respectively.[4]
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
Suitable for the synthesis of acid chlorides used to produce liquid crystals.

Packaging

The 5g, 25g and 100g units sold in the US are packaged in ampules.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

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Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - Water-react 1

Storage Class

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

wgk_germany

WGK 1

flash_point_f

51.8 °F - closed cup

flash_point_c

11.0 °C - closed cup

ppe

Faceshields, Gloves, Goggles


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Catalytic Syntheses of N-Heterocyclic Ynones and Ynediones by In Situ Activation of Carboxylic Acids with Oxalyl Chloride.
Boersch C, et al.
Angewandte Chemie (International Edition in English), 50(44), 10448-10452 (2011)
A simple method for the microscale preparation of Mosher's acid chloride.
Ward DE and Rhee CK.
Tetrahedron Letters, 32(49), 7165-7166 (1991)
Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide" activated" by oxalyl chloride.
Mancuso AJ, et al.
The Journal of Organic Chemistry, 43(12), 2480-2482 (1978)
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
Peter J Manley et al.
Organic letters, 4(18), 3127-3129 (2002-08-31)
[reaction: see text] A mild, practical, one-pot method for the generation of imidoyl chlorides and their subsequent in situ reaction with pyridine-1-oxides is described. The imidoyl chlorides were formed from the reaction of secondary amides with a stoichiometric amount of

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