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135364

Sigma-Aldrich

Diethyl oxalate

≥99%

Synonym(s):

Diethyl ethanedioate, Ethyl oxalate

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About This Item

Linear Formula:
C2H5OCOCOOC2H5
CAS Number:
95-92-1
Molecular Weight:
146.14
Beilstein:
606350
EC Number:
202-464-1
MDL number:
MFCD00009119
UNSPSC Code:
12352100
PubChem Substance ID:
24848078
NACRES:
NA.22
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vapor density

5.03 (vs air)

Quality Level

200

vapor pressure

1 mmHg ( 47 °C)

Assay

≥99%

form

liquid

refractive index

n20/D 1.410 (lit.)

bp

185 °C (lit.)

mp

−41 °C (lit.)

solubility

alcohol: miscible
diethyl ether: miscible
organic solvents: miscible
water: partially soluble

density

1.076 g/mL at 25 °C (lit.)

functional group

ester

SMILES string

CCOC(=O)C(=O)OCC

InChI

1S/C6H10O4/c1-3-9-5(7)6(8)10-4-2/h3-4H2,1-2H3

InChI key

WYACBZDAHNBPPB-UHFFFAOYSA-N

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General description

Diethyl oxalate undergoes transesterification with phenol in the liquid phase over very efficient MoO3/TiO2 solid-acid sol-gel catalysts to form diphenyl oxalate[1]. It undergoes Claisen condensation with active methylene group of ketosteroids to form glyoxalyl derivatives[2]. It undergoes hydrogenation in the presence of high copper contented mesoporous Cu/SBA-15 catalysts to yield ethylene glycol[3].

Application

Diethyl oxalate was used in microemulsion synthesis of ZnO nanoparticles[4]. It was also used in the synthesis of sym-1,4-diphenyl-1,4-dihydro-1,2,4,5-polytetrazine[5].

Signal Word

Danger

Hazard Statements

H302,H314,H373

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B - STOT RE 2 Oral

Target Organs

Kidney

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

167.0 °F - closed cup

Flash Point(C)

75 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB2915
SDBB2132
0000411749
0000411748
0000411749

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Comparison of two novel solution-based routes for the synthesis of equiaxed ZnO nanoparticles.
Elen K, et al.
Journal of Nanomaterials, 2011, 18-18 (2011)
Diethyl oxalate as new reagent for spectrophotometric determination of ketosteroids.
S Görög
Analytical chemistry, 42(6), 560-563 (1970-05-01)
W W Monafo et al.
Surgery, 80(4), 465-473 (1976-10-01)
The wounds of 60 burned patients were treated topically with cerium nitrate, which was applied either as a cream or in aqueous solution. Cerium nitrate has a potent antiseptic effect in human burn wounds, especially against gram negative bacteria and
Novel macromolecules containing sym-tetrazine rings and their subsequent reactions through click modifications.
Sayed RA and Wiggins JS.
Polymer Preprints (American Chemical Society, Division of Polymer Chemistry), 49(1), 188-188 (2008)
One pot synthesis of ultra-high copper contented Cu/SBA-15 material as excellent catalyst in the hydrogenation of dimethyl oxalate to ethylene glycol.
Guo X, et al.
Catalysis Letters, 132(1-2), 22-27 (2009)
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  1. 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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  2. 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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