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O8801

Sigma-Aldrich

Oxalyl chloride

reagent grade, 98%

Synonym(s):

Ethanedioyl dichloride

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25 G
$44.65
100 G
$90.50
6 X 100 G
$368.00
1 KG
$430.35
2.5 KG
$794.00

$44.65

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25 G
$44.65
100 G
$90.50
6 X 100 G
$368.00
1 KG
$430.35
2.5 KG
$794.00

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:
57654494
NACRES:
NA.22

$44.65

List Price$47.00Save 5%
Web-Only Promotion

Available to ship onMay 01, 2025Details

Request a Bulk Order

grade

reagent grade

Quality Level

200

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.)

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 versatile reagent in various chemical transformations, such as chlorination, dichlorination, oxidation, reduction, dehydration, decarboxylation, formylation, and ring cleavage of epoxides.

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

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_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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Certificates of Analysis (COA)

Lot/Batch Number
STBL4586
SHBQ9279
STBL2944
STBL0633
WXBD0931V

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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)
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)
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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Questions

1–3 of 3 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. How is this product packaged?

    1 answer

    1. This product is currently packaged in an amber glass bottle with a sureseal cap.

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