Tetrahydrophthalic anhydride
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Preferred IUPAC name (3aR,7aS)-3a,4,7,7a-Tetrahydro-2-benzofuran-1,3-dione | |
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ECHA InfoCard | 100.012.098 ![]() |
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UN number | 2698 |
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Properties | |
Chemical formula | C8H8O3 |
Molar mass | 152.149 g·mol−1 |
Appearance | white or colorless solid |
Melting point | 97–103 °C (207–217 °F; 370–376 K) |
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Hazard statements | H317, H318, H334, H412 |
Precautionary statements | P261, P272, P273, P280, P285, P302+P352, P304+P341, P305+P351+P338, P310, P321, P333+P313, P342+P311, P363, P501 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references |
Chemical compound
Tetrahydrophthalic anhydride is an organic compound with the formula C6H8C2O3. The compound exists as two isomers, this article being focused on the more common cis isomer. It is a white solid that is soluble in organic solvents.
Preparation and derivatives
Tetrahydrophthalic anhydride, the cis isomer, is prepared by the Diels-Alder reaction of butadiene and maleic anhydride.[1]
Tetrahydrophthalic anhydride is a precursor to other compounds including the dicarboxylic acid tetrahydrophthalic acid as well the tetrahydrophthalimide, which is a precursor to the fungicide Captan. It is also a precursor to 1,2,3,4-butanetetracarboxylic acid.[2]
References
- ^ Arthur C. Cope; Elbert C. Herrick (1950). "cis-Δ4-Tetrahydrophthalic Anhydride". Org. Synth. 50: 93. doi:10.15227/orgsyn.030.0093.
- ^ Nagao, R.; Marumo, F.; Saito, Y.; Asahara, T. (1971). "The Crystal Structure of Butane-1,2,3,4-tetracarboxylic Dianhydride". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 27 (3): 569–572. Bibcode:1971AcCrB..27..569N. doi:10.1107/s0567740871002577.