2-Butenedioic acid, 2-methyl-, (E)-
- Formula: C5H6O4
- Molecular weight: 130.0987
- IUPAC Standard InChI: InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+
- IUPAC Standard InChIKey: HNEGQIOMVPPMNR-NSCUHMNNSA-N
- CAS Registry Number: 498-24-8
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Stereoisomers:
- Other names: Mesaconic acid; trans-1-Propene-1,2-dicarboxylic acid; trans-2-Methyl-2-butenedioic acid; Methylfumaric acid; 2-Methylfumaric acid; (E)-2-Methyl-2-butenedioic acid; Butenedioic acid, methyl-, (E)-; Fumaric acid, methyl-; Mesaconate; Kyselina mesakonova; 2-Butenedioic acid, 2-methyl-, (2E)-; NSC 65438
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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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -824.4 ± 1.5 | kJ/mol | Ccb | Wilhoit and Lei, 1965 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -2000.6 ± 1.4 | kJ/mol | Ccb | Wilhoit and Lei, 1965 | Reanalyzed by Cox and Pilcher, 1970, Original value = -2001.9 kJ/mol; Corresponding ΔfHºsolid = -824.42 kJ/mol (simple calculation by NIST; no Washburn corrections) |
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: C5H4O3 + H2O = C5H6O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -34.0 | kJ/mol | Cm | Conn, Kistiakowsky, et al., 1942 | liquid phase; Heat of hydrolysis at 303 K |
+
=
+
By formula: C5H6O4 + Br2 = C5H6O4 + Br2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -5.1 ± 0.7 | kJ/mol | Eqk | Jwo, Huang, et al., 1987 | solid phase; HPLC |
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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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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| Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| Origin | Sadtler Research Labs Under US-EPA Contract |
| State | gas |
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
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Due to licensing restrictions, this spectrum cannot be downloaded.
| Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| Origin | NIST Mass Spectrometry Data Center, 1994 |
| NIST MS number | 134190 |
UV/Visible 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
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| Source | Jones, Whitham, et al., 1954 |
|---|---|
| Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
| Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
| Source reference | RAS UV No. 2544 |
| Instrument | n.i.g. |
| Melting point | 204.5 |
| Boiling point | sub |
References
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Wilhoit and Lei, 1965
Wilhoit, R.C.; Lei, I.,
Thermochemistry of biologically important compounds. Heats of combustion of five organic acids.,
J. Chem. Eng. Data, 1965, 10, 166-168. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Conn, Kistiakowsky, et al., 1942
Conn, J.B.; Kistiakowsky, G.B.; Roberts, R.M.; Smith, E.A.,
Heats of organic reactions. XIII. Heats of hydrolysis of some acid anhydrides,
J. Am. Chem. Soc., 1942, 64, 1747-17. [all data]
Jwo, Huang, et al., 1987
Jwo, J-J.; Huang, C-Y.; Chang, E-F.; Wu, R.R.,
Kinetic study of the bromine-catalyzed isomerization of methyl- and chloro-maleic acids in aqueous Ce(IV)-Br- -H2SO4 medium,
J. Chin. Chem. Soc. (Taipei), 1987, 34, 247-256. [all data]
Jones, Whitham, et al., 1954
Jones, E.R.H.; Whitham, G.H.; Whiting, M.C.,
Researches on acetylenic compounds. Part XLIV. The reaction between nickel carbonyl and some esters of ω-acetylenic acids,
J. Chem. Soc., 1954, 1865-1868. [all data]
Notes
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- Symbols used in this document:
ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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