Tetrahydrophthalic anhydride

Tetrahydrophthalic anhydride
Names
Preferred IUPAC name
(3aR,7aS)-3a,4,7,7a-Tetrahydro-2-benzofuran-1,3-dione
Identifiers
CAS Number
  • 935-79-5
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:180650
ChEMBL
  • ChEMBL2228342
ChemSpider
  • 88950
ECHA InfoCard 100.012.098 Edit this at Wikidata
EC Number
  • 213-308-7
PubChem CID
  • 98495
RTECS number
  • GW5775000
UNII
  • W9Q4666NOS
UN number 2698
CompTox Dashboard (EPA)
  • DTXSID80883570 Edit this at Wikidata
InChI
  • 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
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)
Hazards
GHS labelling:
Pictograms
 GHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
Danger
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

  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.