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
EC Number	213-308-7;
PubChem CID	98495;
RTECS number	GW5775000;
UNII	W9Q4666NOS;
UN number	2698
CompTox Dashboard (EPA)	DTXSID80883570 ;
	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;
	SMILES 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
Signal word	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

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.

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

[Acta-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.

[1]

[2]