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Tetrahydrophthalic anhydride

From Wikipedia, the free encyclopedia
Tetrahydrophthalic anhydride
Names
Preferred IUPAC name
(3aR,7aS)-3a,4,7,7a-Tetrahydro-2-benzofuran-1,3-dione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.012.098 Edit this at Wikidata
EC Number
  • 213-308-7
RTECS number
  • GW5775000
UNII
UN number 2698
  • InChI=1S/C8H8O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-2,5-6H,3-4H2
    Key: KMOUUZVZFBCRAM-UHFFFAOYSA-N
  • C1C=CCC2C1C(=O)OC2=O
Properties
C8H8O3
Molar mass 152.149 g·mol−1
Appearance white or colorless solid
Melting point 97–103 °C (207–217 °F; 370–376 K)
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
Danger
H317, H318, H334, H412
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).

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

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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

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  1. ^ Arthur C. Cope; Elbert C. Herrick (1950). "cis-Δ4-Tetrahydrophthalic Anhydride". Org. Synth. 50: 93. doi:10.15227/orgsyn.030.0093.
  2. ^ 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.