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135623

Sigma-Aldrich

Dimethyl oxalate

ReagentPlus®, 99%

Synonym(s):

Methyl oxalate

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About This Item

Linear Formula:
CH3OCOCOOCH3
CAS Number:
553-90-2
Molecular Weight:
118.09
Beilstein:
1071744
EC Number:
209-053-6
MDL number:
MFCD00008442
UNSPSC Code:
12352100
PubChem Substance ID:
24848213
NACRES:
NA.22

Quality Level

100

product line

ReagentPlus®

Assay

99%

form

powder

refractive index

n20/D 1.39 (lit.)

bp

163.5 °C (lit.)

mp

50-54 °C (lit.)

solubility

ethanol: soluble 50 mg/mL, clear to very slightly hazy, colorless

density

1.148 g/mL at 25 °C (lit.)

SMILES string

COC(=O)C(=O)OC

InChI

1S/C4H6O4/c1-7-3(5)4(6)8-2/h1-2H3

InChI key

LOMVENUNSWAXEN-UHFFFAOYSA-N

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General description

Dimethyl oxalate undergoes Cu/SiO2 catalyzed hydrogenation to yield ethylene glycol. It undergoes selective gas-phase hydrogenation catalyzed by Ag/SiO2 to yield corresponding alcohol.

Application

Dimethyl oxalate (DMO) was used as alternate fuel in direct oxidation fuel cell. DMO was used to study the IR spectra of DMO isolated in noble gas low-temperature matrices.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314

Hazard Classifications

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

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

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

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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Molecular structure and infrared spectra of dimethyl oxalate.
Lopes SB, et al.
Physical Chemistry Chemical Physics, 4(6), 1014-1020 (2002)
A1h NMR Pulse Gradient Spin-Echo (PGSE) Mass Transport Study of Dimethyl Oxalate and Ethylene Glycol: New Fuels for the DOFC.
Suarez-Gustave S, et al.
Electrochemical and Solid-State Letters, 12(3), 525-528 (2000)
Chao Wen et al.
Chemical communications (Cambridge, England), 49(45), 5195-5197 (2013-05-02)
The variation of the supports on the Cu/SiO2 catalyst plays an important role in the catalytic performance for hydrogenation of dimethyl oxalate. The loss of silica in the form of tetramethoxysilane from the support under the reaction conditions is responsible
Anyuan Yin et al.
Chemical communications (Cambridge, England), 46(24), 4348-4350 (2010-05-14)
Ag/SiO(2) prepared by a sol-gel process is highly effective for selective gas-phase hydrogenation of dimethyl oxalate to corresponding alcohols. The catalysts are of great potential as industrially viable and novel catalysts for the production of methyl glycolate and ethylene glycol.

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