2-Butenedioic acid (Z)-, dimethyl ester

• 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-ARJAWSKDSA-N Copy
• CAS Registry Number: 624-48-6
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Stereoisomers:
  • Dimethyl (2e)-2-butenedioate
  • Dimethyl (2e)-2-butenedioate
  • Dimethyl fumarate
• Other names: Maleic acid, dimethyl ester; Dimethyl cis-ethylenedicarboxylate; Dimethyl maleate; Methyl maleate; Sipomer DMM; Dimethyl cis-butenedioate; 2-Butenedioic acid, dimethyl ester, (Z)-; Dimethylester kyseliny maleinove; 2-Butendioic acid, dimethyl ester, (Z)-; Dimethyl (2Z)-but-2-enedioate; 2-Butenedioic acid (2Z)-, 1,4-dimethyl ester; 2-Butenedioic acid (2Z)-, dimethyl ester
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
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Condensed phase thermochemistry data

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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 liquid

Phase change data

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

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

Reaction thermochemistry data

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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

 +  =

By formula: H₂ + C₆H₈O₄ = C₆H₁₀O₄

Gas phase ion energetics data

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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

IR Spectrum

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

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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Additional Data

Mass spectrum (electron ionization)

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

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

Gas Chromatography

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

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Van Den Dool and Kratz RI, non-polar column, custom temperature program

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References

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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]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Timmermans, 1935
Timmermans, J., Researches in Stoichiometry. I. The Heat of Fusion of Organic Compounds., Bull. Soc. Chim. Belg., 1935, 44, 17-40. [all data]

Wassermann, 1930, 2
Wassermann, A., The Intermolecular Binding Stability of Fumaric and Maleic Acids and Their Dimethyl Esters, Z. Phys. Chem., Abt. A, 1930, 146, 418. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H., Uber sublimationswarmen, Z. Phys. Chem., 1938, 39, 194-208. [all data]

Wolf and Trieschmann, 1934
Wolf, K.L.; Trieschmann, H.G., Z. Phys. Chem. Abt. B, 1934, 27, 376. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Veselova and Sul'man, 1980
Veselova, M.E.; Sul'man, E.M., Effect of the chemical structure of α,β-unsaturated esters and ketones on the selectivity of their hydrogenation, Svoistva Veshchestv i Stroenie Molekul, Kalinin, 1980, 140-143. [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]

Herrmann, Dufka, et al., 1986
Herrmann, F.; Dufka, O.; Churacek, J., Fused-Silica Capillary Gas Chromatography-Mass Spectrometry of Some Dicarboxylic Acids Present in Condensation-Type Polymers I. Dimethyl Esters, J. Chromatogr., 1986, 360, 79-88, https://doi.org/10.1016/S0021-9673(00)91653-4 . [all data]

Tret'yakov, 2007
Tret'yakov, K.V., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [all data]

Notes

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• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔvapH	Enthalpy of vaporization

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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