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Dimethyl oxalate

PubChem CID
11120
Structure
Dimethyl oxalate_small.png
Dimethyl oxalate_3D_Structure.png
Dimethyl oxalate__Crystal_Structure.png
Molecular Formula
Synonyms
  • Dimethyl oxalate
  • 553-90-2
  • METHYL OXALATE
  • Ethanedioic acid, dimethyl ester
  • Oxalic acid dimethyl ester
Molecular Weight
118.09 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2024-12-27
Description
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.
Dimethyl oxalate has been reported in Astragalus mongholicus and Astragalus membranaceus with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Dimethyl oxalate.png

1.2 3D Conformer

1.3 Crystal Structures

1 of 11
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CCDC Number
Crystal Structure Data
Crystal Structure Depiction
Crystal Structure Depiction

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

dimethyl oxalate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C4H6O4/c1-7-3(5)4(6)8-2/h1-2H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

LOMVENUNSWAXEN-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

COC(=O)C(=O)OC
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)

2.2 Molecular Formula

C4H6O4
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

553-90-2

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 DSSTox Substance ID

2.3.6 KEGG ID

2.3.7 Metabolomics Workbench ID

2.3.8 Nikkaji Number

2.3.9 NSC Number

2.3.10 Wikidata

2.3.11 Wikipedia

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
118.09 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
-0.2
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
118.02660867 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
118.02660867 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
52.6Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
8
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
92.6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Colorless solid; [Merck Index] White crystalline aggregates; [MSDSonline]

3.2.2 Vapor Pressure

1.14 [mmHg]

3.2.3 Kovats Retention Index

Standard non-polar
800, 837, 824.3
Semi-standard non-polar
826, 817, 819, 824, 800, 826, 800
Standard polar
1409, 1382, 1382, 1389, 1395, 1409, 1395

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Other Classes -> Esters, Other

3.4.1 Cosmetics

Chelating
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian A-60
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
135623
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
Chem Service, Inc., West Chester, Pennsylvania
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Instrument Name
QE-300
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.1.3 17O NMR Spectra

Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 10
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MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
HITACHI M-80
Instrument Type
CI-B
Ionization Mode
positive
Top 5 Peaks

119 99.99

118 26.66

120 4.03

90 3.06

91 1.79

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License
CC BY-NC-SA
2 of 10
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MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
HITACHI M-80
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

59 99.99

15 32.01

45 29.58

43 4.62

118 4.36

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License
CC BY-NC-SA

4.2.2 Other MS

1 of 5
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Authors
TAJIMA S, GUNMA COLLEGE OF TECHNOLOGY
Instrument
HITACHI RMU-7M
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

59 999

15 991

45 347

29 142

31 55

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License
CC BY-NC-SA
2 of 5
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Authors
YAMAMOTO M, DEP. CHEMISTRY, FAC. SCIENCE, NARA WOMEN'S UNIV.
Instrument
HITACHI RMU-6M
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

15 999

59 932

45 323

29 183

31 66

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License
CC BY-NC-SA

4.3 IR Spectra

4.3.1 FTIR Spectra

1 of 2
Instrument Name
Bruker IFS 85
Technique
KBr-Pellet
Source of Sample
Merck-Schuchardt Hohenbrunn
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
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2 of 2
Instrument Name
Bruker IFS 85
Technique
KBr-Pellet
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.3.2 ATR-IR Spectra

Source of Sample
Aldrich
Catalog Number
135623
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.3.3 Vapor Phase IR Spectra

1 of 2
Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
135623
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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4.4 Raman Spectra

Catalog Number
135623
Copyright
Copyright © 2017-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2017-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Use and Manufacturing

7.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125

7.1.1 Use Classification

Cosmetics -> Chelating
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

7.1.2 Industry Uses

Intermediate

7.1.3 Consumer Uses

Intermediate

7.2 U.S. Production

Aggregated Product Volume
2016: 32,043 lb

7.3 General Manufacturing Information

Industry Processing Sectors
All Other Basic Organic Chemical Manufacturing
EPA TSCA Commercial Activity Status
Ethanedioic acid, 1,2-dimethyl ester: ACTIVE

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 GHS Classification

1 of 2
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Note
Pictograms displayed are for 98.8% (84 of 85) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 1.2% (1 of 85) of reports.
Pictogram(s)
Corrosive
Irritant
Signal
Danger
GHS Hazard Statements

H302 (31.8%): Harmful if swallowed [Warning Acute toxicity, oral]

H314 (25.9%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

H315 (72.9%): Causes skin irritation [Warning Skin corrosion/irritation]

H318 (20%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H319 (72.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Precautionary Statement Codes

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

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 85 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 1 of 85 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 10 notifications provided by 84 of 85 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

8.1.2 Hazard Classes and Categories

Acute Tox. 4 (31.8%)

Skin Corr. 1B (25.9%)

Skin Irrit. 2 (72.9%)

Eye Dam. 1 (20%)

Eye Irrit. 2 (72.9%)

Acute toxicity - category 4

Skin corrosion - category 1B

Specific target organ toxicity (repeated exposure) - category 2

8.1.3 Hazards Summary

A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; [MSDSonline]

8.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Ethanedioic acid, dimethyl ester
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Ethanedioic acid, dimethyl ester: Does not have an individual approval but may be used under an appropriate group standard

8.3 Other Safety Information

Chemical Assessment

IMAP assessments - Ethanedioic acid, dimethyl ester: Environment tier I assessment

IMAP assessments - Oxalate esters (C1-C4): Human health tier II assessment

9 Toxicity

9.1 Toxicological Information

9.1.1 Adverse Effects

Dermatotoxin - Skin burns.

Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

9.1.2 Acute Effects

10 Literature

10.1 Consolidated References

10.2 Springer Nature References

10.3 Thieme References

10.4 Wiley References

10.5 Chemical Co-Occurrences in Literature

10.6 Chemical-Gene Co-Occurrences in Literature

10.7 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

11.4 Chemical-Disease Co-Occurrences in Patents

11.5 Chemical-Gene Co-Occurrences in Patents

12 Biological Test Results

12.1 BioAssay Results

13 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

14 Classification

14.1 ChEBI Ontology

14.2 ChemIDplus

14.3 UN GHS Classification

14.4 EPA CPDat Classification

14.5 NORMAN Suspect List Exchange Classification

14.6 EPA DSSTox Classification

14.7 EPA TSCA and CDR Classification

14.8 LOTUS Tree

14.9 EPA Substance Registry Services Tree

14.10 MolGenie Organic Chemistry Ontology

15 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  5. EPA Chemical Data Reporting (CDR)
    LICENSE
    The U.S. Government retains a nonexclusive, royalty-free license to publish or reproduce these documents, or allow others to do so, for U.S. Government purposes. These documents may be freely distributed and used for non-commercial, scientific and educational purposes.
    https://www.epa.gov/web-policies-and-procedures/epa-disclaimers#copyright
    Ethanedioic acid, 1,2-dimethyl ester
    https://www.epa.gov/chemical-data-reporting
  6. EPA Chemicals under the TSCA
    Ethanedioic acid, 1,2-dimethyl ester
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  7. EPA DSSTox
    Ethanedioic acid, dimethyl ester
    https://comptox.epa.gov/dashboard/DTXSID9060287
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  8. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  9. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  10. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  11. ChEBI
  12. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  13. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  14. The Cambridge Structural Database
  15. EPA Chemical and Products Database (CPDat)
  16. Hazardous Chemical Information System (HCIS), Safe Work Australia
  17. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  18. Japan Chemical Substance Dictionary (Nikkaji)
  19. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  20. MassBank Europe
  21. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  22. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  23. SpectraBase
    ETHANEDIOIC ACID, DIMETHYL ESTER
    https://spectrabase.com/spectrum/HifhcE6zrR
    Ethanedioic acid, dimethyl ester
    https://spectrabase.com/spectrum/EeiHbnenMhq
    ETHANEDIOIC ACID, DIMETHYL ESTER
    https://spectrabase.com/spectrum/EUV3uvOQxvK
    Ethanedioic acid, dimethyl ester
    https://spectrabase.com/spectrum/6VehFHbzG2o
    Ethanedioic acid, dimethyl ester
    https://spectrabase.com/spectrum/LHuu5f5QDri
  24. Metabolomics Workbench
  25. NMRShiftDB
  26. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  27. Springer Nature
  28. SpringerMaterials
  29. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  30. Wikidata
  31. Wikipedia
  32. Wiley
  33. PubChem
  34. GHS Classification (UNECE)
  35. EPA Substance Registry Services
  36. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  37. PATENTSCOPE (WIPO)
CONTENTS