Basic information
- CAS
553-90-2- Standard SMILES
COC(=O)C(=O)OC- InChIKey
LOMVENUNSWAXEN-UHFFFAOYSA-N- Molecular formula
- C4H6O4
- Average molar mass
- 118.09 g/mol
- Monoisotopic mass
- 118.02660867
Overview
Methyl oxalate is a member of dicarboxylic acids and O-substituted derivatives, a methyl ester and a diester. It is functionally related to an oxalic acid.
Names & identifiers
- Preferred name
- Dimethyl oxalate
- IUPAC
- dimethyl oxalate
- English name
- Dimethyl oxalate
- Molecular formula
- C4H6O4
- Molecular weight
- 118.09
Names & synonyms
Dimethyl oxalate553-90-2METHYL OXALATEOxalic acid dimethyl esterEthanedioic acid, dimethyl esterDimethyloxalateOxalic acid, dimethyl esterdimethyl ethanedioateMFCD00008442IQ3Q79344SNSC-9374Ethanedioic acid, 1,2-dimethyl ester
Show more names
DMOOXALIC ACID METHYL ESTERDimethyl ester of oxalic acid209-053-6CH3OCOCOOCH3Oxalic acid Me
dimethyl ethane-1,2-dioateNSC 9374EINECS 209-053-6UNII-IQ3Q79344SAI3-21214SCHEMBL8295METHYL OXALATE [MI]CHEBI:6859
Database identifiers
- CAS
553-90-2- PubChem CID
- 11120
- DTXSID
DTXSID9060287- ChEBI
CHEBI:6859- UNII
- IQ3Q79344S
- EC Number
- 209-053-6
- Nikkaji
- J2.653K
Properties
Computed structural properties
- XLogP
- -0.2
- Topological polar surface area
- 52.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 92.6
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Esters, Other
CosmeticsChelating
SpringerMaterials PropertiesBoiling point
LogP-0.17
Density1.148 @25 °C
Boiling Point163.5 °C @760 [mm Hg]
Vapor Pressure1.14 [mmHg]
Physical DescriptionColorless solid; [Merck Index] White crystalline aggregates; [MSDSonline]
Physicochemical properties
- Melting point
- 50 · 50-54 °C (lit.)
- Boiling point
- 163.5 °C · 163.5 °C (lit.)
- Density
- 1.148 g/mL · 1.148 g/mL at 25 °C (lit.)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 0.5% (1 of 191) of reports.
Danger
H302 (69.6%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P321, P330, P332+P317, P337+P317, P362+P364, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 191 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
Hazard information
Regulatory Information
Chemical: Ethanedioic acid, dimethyl ester
Ethanedioic acid, 1,2-dimethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanedioic acid, 1,2-dimethyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 19-11-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/25766
Ethanedioic acid, dimethyl ester: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Ethanedioic acid, dimethyl ester: Environment tier I assessment
Hazards SummaryA corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; [MSDSonline]
Hazard Classes and Categories
Acute Tox. 4 (69.6%)
Acute toxicity - category 4
Chemistry & industry
Uses & manufacturing
U.S. Production2020: 84,920 lb
Use ClassificationCosmetics -> Chelating
General Manufacturing InformationEthanedioic acid, 1,2-dimethyl ester: ACTIVE
Applications
DescriptionDimethyl oxalate is a chemical compound with formula (CH3)2(COO)2. It is the dimethyl ester of oxalic acid.
General DescriptionDimethyl oxalate (DMO), (CH3OCO)2 is an industrial chemical intermediate with versatile properties. DMO is used as a solvent and extraction agent to produce ethylene glycol, ethanol, oxalic acid, oxamide, dyes, and medicines. Besides, dimethyl carbonate (DMC), (CH3O)2CO is attracting lots of interest because of its excellent solubility, biodegradability and low toxicity. DMC could be used as a green solvent, as electrolytes in lithium batteries, as a potential fuel additive and for polycarbonate synthesis[1].
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.
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.
Upstream & downstream products
Upstream raw materials
Related reactions
220 records
Compound notes
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