Dimethyl fumarate
- Formula: C6H8O4
- Molecular weight: 144.1253
- IUPAC Standard InChIKey: LDCRTTXIJACKKU-ONEGZZNKSA-N
- 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
The 3d structure may be viewed using Java or Javascript. - Species with the same structure:
- Stereoisomers:
- 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
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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 solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
47.61 | 298. | Wassermann, 1930 | T = 014 to 99°C. |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 466.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 374.7 | K | N/A | de Wolf and Van de Straete, 1935 | Uncertainty assigned by TRC = 0.6 K; TRC |
Tfus | 375. | K | N/A | Wassermann, 1930, 2 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 375. | K | N/A | Padoa, 1919 | Uncertainty assigned by TRC = 1. K; TRC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
12.9 | 376. | A | Stephenson and Malanowski, 1987 | Based on data from 361. to 466. K.; AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
20.2 ± 0.5 | 283. | V | Wolf and Weghofer, 1938 | ALS |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.401 | 375. | Domalski and Hearing, 1996 | AC |
8.4011 | 375. | Wassermann, 1930 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
22. | 375. | Wassermann, 1930 | DH |
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
+
= C26H22O5
By formula: C20H14O + C6H8O4 = C26H22O5
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -15. | kcal/mol | Kin | Samuilov, Nurullina, et al., 1983 | liquid phase; solvent: Dichloroethane |
ΔrH° | -15. | kcal/mol | Kin | Samuilov, Nurullina, et al., 1983 | liquid phase; solvent: Nonaquous |
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
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.5 | PE | Kobayashi, Yokota, et al., 1975 | Vertical value |
10.70 | PE | Sustmann and Trill, 1972 | Vertical value |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Ultra-1 | 100. | 993. | Herrmann, Dufka, et al., 1986 | 25. m/0.20 mm/0.32 μm, N2 |
Capillary | Ultra-1 | 125. | 993. | Herrmann, Dufka, et al., 1986 | 25. m/0.20 mm/0.32 μm, N2 |
Capillary | Ultra-1 | 150. | 993. | Herrmann, Dufka, et al., 1986 | 25. m/0.20 mm/0.32 μm, N2 |
Capillary | Ultra-1 | 75. | 994. | Herrmann, Dufka, et al., 1986 | 25. m/0.20 mm/0.32 μm, N2 |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-1 | 993. | Peters, de Leer, et al., 1994 | 25. m/0.2 mm/0.33 μm, He, 50. C @ 5. min, 8. K/min, 300. C @ 10. min |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-30 | 997. | Vinogradov, 2004 | Program: not specified |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, 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]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
de Wolf and Van de Straete, 1935
de Wolf, J.; Van de Straete, L.,
Maleonitrile and Fumaronitrole,
Bull. Cl. Sci., Acad. R. Belg., 1935, 21, 216. [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]
Padoa, 1919
Padoa, M.,
Atti Accad. Naz. Lincei, Cl. Sci. Fis., Mat. Nat., Rend., 1919, 28, 239. [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]
Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H.,
Uber sublimationswarmen,
Z. Phys. Chem., 1938, 39, 194-208. [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]
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]
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]
Peters, de Leer, et al., 1994
Peters, R.J.D.; de Leer, E.W.B.; Versteegh, J.F.M.,
Identification of Halogenated Compounds Produced by Chlorination of Humic Acid in the Presence of Bromide,
J. Chromatogr. A, 1994, 686, 2, 253-261, https://doi.org/10.1016/0021-9673(94)00719-5
. [all data]
Vinogradov, 2004
Vinogradov, B.A.,
Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid 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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