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8.07066

Sigma-Aldrich

Oxalyl chloride

for synthesis

Synonym(s):

Oxalyl chloride, Oxalic acid dichloride

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About This Item

Empirical Formula (Hill Notation):
C2Cl2O2
CAS Number:
Molecular Weight:
126.93
MDL number:
UNSPSC Code:
12352106
EC Index Number:
201-200-2
NACRES:
NA.22
Pricing and availability is not currently available.

vapor pressure

200 hPa ( 20 °C)

Quality Level

form

liquid

bp

63-64 °C/1013 hPa

mp

-12 °C

transition temp

flash point >100 °C

density

1.48 g/cm3 at 20 °C

storage temp.

2-30°C

SMILES string

ClC(=O)C(=O)Cl

InChI

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

InChI key

CTSLXHKWHWQRSH-UHFFFAOYSA-N

Application

  • Mild deprotection of the N-tert-butyloxycarbonyl (N-Boc) group using oxalyl chloride: This study explores the mild deprotection capabilities of oxalyl chloride on N-Boc substrates, offering a potential method for sensitive chemical syntheses (N George, S Ofori, S Parkin, SG Awuah, 2020).
  • Nickel-Catalyzed Highly Selective Reductive Carbonylation Using Oxalyl Chloride as the Carbonyl Source: Demonstrates the use of oxalyl chloride as an effective carbonyl source in nickel-catalyzed reductive carbonylation, highlighting its utility in organic synthesis (J Wang, Y Yin, X He, QL Duan, R Bai, HW Shi, 2023).
  • A novel and highly efficient esterification process using triphenylphosphine oxide with oxalyl chloride: Introduces a novel esterification process utilizing oxalyl chloride and triphenylphosphine oxide, which improves reaction efficiency and product yield in organic chemistry (M Jia, L Jiang, F Niu, Y Zhang, 2018).
  • Dimethyl sulfoxide/oxalyl chloride: A useful reagent for sulfenyletherification: Discusses the use of a dimethyl sulfoxide/oxalyl chloride mixture in sulfenyletherification reactions, providing insights into advanced synthesis techniques for sulfur-containing compounds (Y Gao, S Cheng, T Zhang, R Ding, Y Liu, 2018).

Analysis Note

Assay (argentometric): ≥ 98.0 %
Identity (IR): passes test
A slight precipitate of oxalic acid is normal and does not affect the specified quality of the product.

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Supplementary Hazards

Storage Class Code

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


Certificates of Analysis (COA)

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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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