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221015

Sigma-Aldrich

Oxalyl chloride

Oxalyl chloride
1 of 2 reviewers received a sample product or took part in a promotion

ReagentPlus®, ≥99%

Synonym(s):

Ethanedioyl dichloride

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5 G
$28.70
25 G
$71.30
100 G
$132.00
10 KG
$2,100.00

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5 G
$28.70
25 G
$71.30
100 G
$132.00
10 KG
$2,100.00

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:
24853204
NACRES:
NA.22
form:
liquid
assay:
≥99%

$28.70

In StockDetails

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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.)

functional group

acyl chloride

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.[1]

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.[2]
  • Activation of dimethyl sulfoxide for use in the oxidation of long-chain alcohols to carbonyls.[3]
  • Activation of α-keto carboxylic acids and N-heterocyclic carboxylic acids for alkynylation to form ynediones and N-heterocyclic ynones, respectively.[4]
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

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Description
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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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV5569
MKCV9052
MKCV7172
MKCW5425
MKCW0334

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A simple method for the microscale preparation of Mosher's acid chloride.
Ward DE and Rhee CK.
Tetrahedron Letters, 32(49), 7165-7166 (1991)
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)
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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2 Reviews This action will navigate to reviews.

Questions

1–2 of 2 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

      Helpful?

  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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Reviews

1 of 2 reviewers received a sample product or took part in a promotion
1–2 of 2 Reviews  

Active Filters

  1. UW-Madison
    • Review 1
    • Votes 28
    1 out of 5 stars.

    Packed in ampules, not bottles

    Beware of the packaging! This reagent comes in glass ampules - impossible to re-seal! We got 100 g, and only used 5 mls.

    Helpful?

    1. Response from MilliporeSigma:

      Thank you for your review. We are sorry to hear that your experience did not match your product expectations. Although we do list the packaging description as "5, 25, 100 g in ampule", we have raised the suggestion with our product management team to make the product packaging more apparent.

  2. Waterloo
    • Review 1
    • Votes 8
    1 out of 5 stars.

    Incomplete Information

    The website makes no mention of the product being shipped in a glass ampoule, so now we'd have to waste 99% of it just to run a single reaction. I see a previous review made the same complaint with no update from Sigma.

    Helpful?

    1. Response from MilliporeSigma:

      Thank you for bringing this issue to our attention. To follow up on the previous issue that was raised, the packaging for this material is region dependent. We have added the clarification "The 5g, 25g and 100g units sold in the US are packaged in ampules." to the Packaging description.

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