- Formula: C9H8O3
- Molecular weight: 164.1580
- IUPAC Standard InChI:
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- IUPAC Standard InChIKey: KNDQHSIWLOJIGP-ZTYPAOSTSA-N
- CAS Registry Number: 129-64-6
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
- Other names: (3a«alpha»,4«alpha»,7«alpha»,7a«alpha»)-3a,4,7,7a-Tetrahydro-4,7-methano-isobenzofuran-1,3-dione; 4,7-Methanoisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydro-, (3a«alpha»,4«alpha»,7«alpha»,7a«alpha»)-; 8,9,10-Trinorborn-5-ene-2,3-dicarboxylic anhydride; endo-Himic acid anhydride; endo-3,6-Methylene-1,2,3,6-tetrahydrophthalic anhydride; endo-5-Norbornene-2,3-dicarboxylic anhydride; endo,cis-5-Norbornene-2,3-dicarboxylic anhydride; Endic anhydride; Nadic anhydride; 3,6-Endomethylene-«delta»4-tetrahydrophthalic anhydride; 5-Norbornene-endo-2,3-dicarboxylic anhydride; 5-Norbornene-2,3-dicarboxylic anhydride, cis-endo-; 4,7-Methanoisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydro-, (3aR,4S,7R,7aS)-rel-; Bicyclo[2.2.1hept-5-ene-2-endo,3-endo-dicarboxylic anhydride; Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid endo-cis-anhydride; cis-5-Norbornene-endo-2,3-dicarboxylic anhydride; NSC 102277
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Phase change data
Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes
Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Kenneth Kroenlein director
AC - William E. Acree, Jr., James S. Chickos
|Ttriple||435.4||K||N/A||Weinstein, Leffler, et al., 1984||Crystal phase 1 phase; Uncertainty assigned by TRC = 1. K; TRC|
|subH°||23. ± 1.0||kcal/mol||MG||Rogers and Quan, 1973||See also Pedley and Rylance, 1977.; AC|
Enthalpy of fusion
|fusH (kcal/mol)||Temperature (K)||Reference||Comment|
|0.887||437.2||Pincock, Wilson, et al., 1967||AC|
Reaction thermochemistry data
Go To: Top, Phase change data, Mass spectrum (electron ionization), References, Notes
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.
By formula: C4H2O3 + C5H6 = C9H8O3
|rH°||-24.8 ± 0.5||kcal/mol||Cm||Breslauer and Kabakoff, 1974||liquid phase; solvent: Dioxane|
|rH°||-25.78||kcal/mol||Cm||Rogers and Quan, 1973||liquid phase; Gas phase Diels-Alder|
Mass spectrum (electron ionization)
Go To: Top, Phase change data, Reaction thermochemistry data, References, Notes
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
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|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||Dmitri Zagorevskii, University of Ottawa, Ontario, Canada|
|NIST MS number||284367|
Go To: Top, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), Notes
Weinstein, Leffler, et al., 1984
Weinstein, D.I.; Leffler, A.J.; Currie, J.A., Phase Transitions in Bicyclic Compounds, Mol. Cryst. Liq. Cryst., 1984, 104, 95. [all data]
Rogers and Quan, 1973
Rogers, F.E.; Quan, S.W., Thermochemistry of the Diels-Alder reaction. III. Heat of addition of cyclopentadience to maleic anhydride, J. Phys. Chem., 1973, 77, 828-831. [all data]
Pedley and Rylance, 1977
Pedley, J.B.; Rylance, J., , Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, Brighton, 1977. [all data]
Pincock, Wilson, et al., 1967
Pincock, Richard E.; Wilson, Keith R.; Kiovsky, Thomas E., Thermal isomerization in polycrystalline exo- and endo-5-norbornene-2,3-dicarboxylic anhydrides, J. Am. Chem. Soc., 1967, 89, 26, 6890-6897, https://doi.org/10.1021/ja01002a015 . [all data]
Breslauer and Kabakoff, 1974
Breslauer, K.J.; Kabakoff, D.S., Enthalpy of the Diels-Alder reaction of cyclopentadiene and maleic anhydride, J. Org. Chem., 1974, 39, 721-722. [all data]
Go To: Top, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References
- Symbols used in this document:
Ttriple Triple point temperature fusH Enthalpy of fusion rH° Enthalpy of reaction at standard conditions subH° Enthalpy of sublimation at standard conditions
- Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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