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310670

Sigma-Aldrich

Oxalyl chloride solution

2.0 M in methylene chloride

Synonym(s):

Dichlorooxalic acid, Ethanedioyl chloride, Oxalic acid chloride, Oxalic acid dichloride, Oxalic dichloride, Oxaloyl chloride, Oxaloyl dichloride, Oxalyl dichloride

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About This Item

Linear Formula:
ClCOCOCl
CAS Number:
79-37-8
Molecular Weight:
126.93
Beilstein:
1361988
MDL number:
MFCD00000704
UNSPSC Code:
12352106
PubChem Substance ID:
24858810
NACRES:
NA.22

form

liquid

reaction suitability

reagent type: oxidant

concentration

2.0 M in methylene chloride

density

1.335 g/mL at 25 °C

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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Application

Oxalyl chloride is generally used as a dimethyl sulfoxide activator and a chlorinating agent to convert carboxylic acid to acid chlorides.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Skin Corr. 1B - STOT SE 3 - Water-react 1

Target Organs

Central nervous system

Supplementary Hazards

EUH014,EUH029,EUH071

Storage Class Code

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

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Catalytic syntheses of N-heterocyclic ynones and ynediones by in situ activation of carboxylic acids with oxalyl chloride.
Christina Boersch et al.
Angewandte Chemie (International ed. in English), 50(44), 10448-10452 (2011-09-13)
Synthesis and characterization of highly soluble and heat stable new poly (amide-ether) s containing pyridine rings in the main chain.
Banihashemi A and Vakili MR
e-Polymers, 8(1) (2008)
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)
Tsutomu Kimura et al.
Chemical communications (Cambridge, England), (32)(32), 4077-4079 (2005-08-11)
Reaction of diastereomerically pure phosphinoselenoic acid salts with oxalyl chloride leads to enantiomerically pure P-chiral phosphinoselenoic chlorides with inversion of configuration at phosphorus; one of these chlorides is converted to a phosphinoselenothioic acid salt with a high degree of enantioselectivity.
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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