Tetrahydrophthalic anhydride

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 precursor to other compounds including the dicarboxylic acid tetrahydrophthalic acid as well the tetrahydrophthalimide, which is a precursor to the fungicide Captan. It is a white solid that is soluble in organic solvents.

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
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).
Infobox references

Tetrahydrophthalic anhydride, the cis isomer, is prepared by the Diels-Alder reaction of butadiene and maleic anhydride.[1]

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