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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/REAXYS Number:
606350
EC Number:
202-464-1
MDL number:
MFCD00009119
UNSPSC Code:
12352100
PubChem Substance ID:
24848078
NACRES:
NA.22

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.)

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. It undergoes Claisen condensation with active methylene group of ketosteroids to form glyoxalyl derivatives. It undergoes hydrogenation in the presence of high copper contented mesoporous Cu/SBA-15 catalysts to yield ethylene glycol.

Application

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

signalword

Danger

Hazard Classifications

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

target_organs

Kidney

Storage Class

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

wgk_germany

WGK 1

flash_point_f

167.0 °F - closed cup

flash_point_c

75 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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
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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