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221015

Sigma-Aldrich

Oxalyl chloride

ReagentPlus®, ≥99%

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Synonym(s):
Ethanedioyl dichloride
Linear Formula:
ClCOCOCl
CAS Number:
79-37-8
Molecular Weight:
126.93
Beilstein:
1361988
EC Number:
201-200-2
MDL number:
MFCD00000704
UNSPSC Code:
12352106
PubChem Substance ID:
24853204
NACRES:
NA.22

vapor density

4.4 (vs air)

Quality Level

200

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.)

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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General description

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

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.
  • Activation of dimethyl sulfoxide for use in the oxidation of long-chain alcohols to carbonyls.
  • Activation of α-keto carboxylic acids and N-heterocyclic carboxylic acids for alkynylation to form ynediones and N-heterocyclic ynones, respectively.
Suitable for the synthesis of acid chlorides used to produce liquid crystals.
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

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

accessory

Product No.
Description
Pricing

Signal Word

Danger

Hazard Classifications

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

Supplementary Hazards

EUH014,EUH029,EUH071

WGK

WGK 1

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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.
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)
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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