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Merck
CN

O8801

Oxalyl chloride

reagent grade, 98%

Synonym(s):

Ethanedioyl dichloride

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About This Item

Linear Formula:
ClCOCOCl
CAS Number:
79-37-8
Molecular Weight:
126.93
UNSPSC Code:
12352106
NACRES:
NA.22
PubChem Substance ID:
57654494
EC Number:
201-200-2
Beilstein/REAXYS Number:
1361988
MDL number:
MFCD00000704

Key Documents

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Product Name

Oxalyl chloride, reagent grade, 98%

InChI key

CTSLXHKWHWQRSH-UHFFFAOYSA-N

InChI

1S/C2Cl2O2/c3-1(5)2(4)6

SMILES string

ClC(=O)C(Cl)=O

grade

reagent grade

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.)

Quality Level

200

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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

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.

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

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Faceshields, Gloves, Goggles

Regulatory Information

监管及禁止进口产品
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Certificates of Analysis (COA)

Lot/Batch Number
SHBQ9279
STBL4586
STBL2944
STBL0633
WXBD0931V

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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)
A direct access to α-diones from oxalyl chloride.
Babudri F, et al.
Tetrahedron Letters, 36(40), 7305-7308 (1995)
Oxalyl chloride as a practical carbon monoxide source for carbonylation reactions.
Hansen SVF and Ulven T.
Organic Letters, 17(11), 2832-2835 (2015)
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)
Benoît Heurtaux et al.
The Journal of organic chemistry, 70(4), 1474-1477 (2005-02-12)
[reaction: see text] Several natural pulvinic acids were synthesized. Silyl ketene acetals derived from methyl arylacetates (4 equiv) reacted with oxalyl chloride at -78 degrees C, without the need of adding a catalyst. After treatment of the crude diketones with
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