Dimethyl fumarate

• Formula: C₆H₈O₄
• Molecular weight: 144.1253
• IUPAC Standard InChI: InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+ Copy

  
• IUPAC Standard InChIKey: LDCRTTXIJACKKU-ONEGZZNKSA-N Copy
• CAS Registry Number: 624-49-7
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  View 3d structure (requires JavaScript / HTML 5)
• Species with the same structure:
  • Dimethyl (2e)-2-butenedioate
  • Dimethyl (2e)-2-butenedioate
• Stereoisomers:
  • 2-Butenedioic acid (Z)-, dimethyl ester
• Other names: 2-Butenedioic acid (E)-, dimethyl ester; Fumaric acid, dimethyl ester; trans-Butenedioic acid dimethyl ester; trans-1,2-Ethylenedicarboxylic acid dimethyl ester; Allomaleic acid dimethyl ester; Boletic acid dimethyl ester; Dimethyl trans-ethylenedicarboxylate; Ethylene, 1,2-bis(methoxycarbonyl)-, trans-; Methyl fumarate; (E)-CH3OC(O)CH=CHC(O)OCH3; 2-Butenedioic acid, dimethyl ester, (E)-; Dimethylester kyseliny fumarove; (E)-But-2-enedioic acid dimethyl ester; 2-Butenedioic acid (2E)-, 1,4-dimethyl ester; NSC 167432; NSC 25942; 2-Butenedioic acid (2E)-, dimethyl ester
• Information on this page:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Condensed phase thermochemistry data

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of solid

Reaction thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

 +  = C₂₆H₂₂O₅

By formula: C₂₀H₁₄O + C₆H₈O₄ = C₂₆H₂₂O₅

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

References

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Wassermann, 1930
Wassermann, A., Die zwischenmolekularen Bindungsfestigkeiten der Fumar- und Maleinsäure and ihrer Dimethylester, Z. Physik. Chem., 1930, A146, 418-445. [all data]

Samuilov, Nurullina, et al., 1983
Samuilov, Ya.D.; Nurullina, R.L.; Konovalov, A.I., Thermochemical and kinetic study of the Diels-Alder reaction with ethylene and acetylene dienophiles, Zh. Org. Khim., 1983, 19, 1431-1435. [all data]

Kobayashi, Yokota, et al., 1975
Kobayashi, T.; Yokota, K.; Nagakura, S., Photoelectron spectra of the cis- trans-isomers of some ethylene derivatives, Bull. Chem. Soc. Jpn., 1975, 48, 412. [all data]

Sustmann and Trill, 1972
Sustmann, R.; Trill, H., Photoelektronenspektroskopische Bestimmung von Substituenten-Effekten. II. α,β-ungesattigte Carbonester, Tetrahedron Lett., 1972, 42, 4271. [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  ΔrH°	Enthalpy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.