Dimethyl oxalate

Dimethyl oxalate Basic information
Product Name:Dimethyl oxalate
Synonyms:OXALIC ACID BIS-METHYL ESTER;CH3OCOCOOCH3;Dimethyl ester of oxalic acid;Ethanedioc acid dimethyl ester;Ethanedioicacid,dimethylester;Ethanedioicaciddimethylester;Oxalicdimethylester;ETHANEDIOIC ACID,BIS-METHYL ESTER
CAS:553-90-2
MF:C4H6O4
MW:118.09
EINECS:209-053-6
Product Categories:Organics;Pyridines;Pharmaceutical Intermediates;C2 to C5;Carbonyl Compounds;Esters;K00001
Mol File:553-90-2.mol
Dimethyl oxalate Structure
Dimethyl oxalate Chemical Properties
Melting point 50-54 °C (lit.)
Boiling point 163.5 °C (lit.)
density 1.148 g/mL at 25 °C (lit.)
vapor pressure 3 hPa (20 °C)
refractive index n20/D 1.39(lit.)
Fp 167 °F
storage temp. Store below +30°C.
solubility ethanol: soluble50mg/mL, clear to very slightly hazy, colorless
form Crystalline Solid
Specific Gravity1.148
color Colorless to white
PH1 (60g/l, H2O, 20℃)
Water Solubility 60 G/L (25 ºC)
Merck 14,6106
BRN 1071744
Stability:Stable. Combustible. Incompatible with strong oxidizing agents, acids, bases, reducing agents.
InChIKeyLOMVENUNSWAXEN-UHFFFAOYSA-N
LogP-0.170
CAS DataBase Reference553-90-2(CAS DataBase Reference)
NIST Chemistry ReferenceEthanedioic acid, dimethyl ester(553-90-2)
EPA Substance Registry SystemEthanedioic acid, dimethyl ester (553-90-2)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 36/38-36-22
Safety Statements 26-36/37-24/25-23
RIDADR 1759
WGK Germany 3
RTECS RO2850000
Autoignition Temperature480 °C
TSCA Yes
HS Code 2917 11 00
HazardClass 6.1(b)
PackingGroup III
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
Dimethyl oxalate Usage And Synthesis
DescriptionDimethyl oxalate is a chemical compound with formula (CH3)2(COO)2. It is the dimethyl ester of oxalic acid.
Chemical Propertiescolourless crystals
Chemical PropertiesThe empirical formula of dimethyl oxalate is C4H6O4. It exists as a liquid between its pour point (52°C) and boiling point (163.4°C). It is soluble in ethanol and ether and slightly soluble in water.
UsesDimethyl oxalate is used as an alternate fuel in the direct oxidation fuel cell. It is involved in the catalytic hydrogenation using Cu/SiO22ub> to prepare ethylene glycol. It is also used in the selective gas-phase hydrogenation catalyzed by Ag/SiO2 to get the corresponding alcohol.
DefinitionChEBI: Methyl oxalate is a diester, a methyl ester and a member of dicarboxylic acids and O-substituted derivatives. It is functionally related to an oxalic acid.
Synthesis Reference(s)The Journal of Organic Chemistry, 24, p. 261, 1959 DOI: 10.1021/jo01084a633
General DescriptionDimethyl oxalate undergoes Cu/SiO2 catalyzed hydrogenation to yield ethylene glycol. It undergoes selective gas-phase hydrogenation catalyzed by Ag/SiO2 to yield corresponding alcohol.
Purification MethodsCrystallise the ester repeatedly from EtOH. De-gas it under nitrogen at high vacuum and distil it. [Beilstein 2 IV 1847.]
DIMETHYL PIMELATE Methyl Methyl vanillate Dimethyl adipate Dimethyl oxalate Bensulfuron methyl OXALIC ACID Parathion-methyl idene)-dimethyl-,oxalate(2:1),oxalate(1:1 Kresoxim-methyl Dimethyl sulfide 2-dihtiolan-4-amine,n,n-dimethyl-oxalate(1:1 Thiophanate-methyl Dimethyl sebacate Methyl acrylate Methyl bromide METHYL THIOPHENE-2-CARBOXYLATE Dimethyl sulfate

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