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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:
79-37-8
Molecular Weight:
126.93
Beilstein/REAXYS Number:
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

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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

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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