Anthracene–maleic anhydride adduct

Anthracene–maleic anhydride adduct
Names
	Systematic IUPAC name (15S,19R)-17-oxapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaene-16,18-dione
	Other names 9,10-dihydroanthracene-9,10-endo-α,β-succinic anhydride; endo-9,10-(α,β-Succinic anhydride)anthracene; 9,10-Ethanoanthracene-11,12-dicarboxylic anhydride; Dibenzobarallene;
Identifiers
3D model (JSmol)	Interactive image;
PubChem CID	11807956;
	InChI InChI=1S/C18H12O3/c19-17-15-13-9-5-1-2-6-10(9)14(16(15)18(20)21-17)12-8-4-3-7-11(12)13/h1-8,13-16H/t13?,14?,15-,16+ Key: PSKVQQJLLWSBFV-STONLHKKSA-N;
	SMILES C1=CC=C2C3[C@@H]4[C@H](C(C2=C1)C5=CC=CC=C35)C(=O)OC4=O;
Properties
Chemical formula	C18H12O3
Molar mass	276.291 g·mol−1
Appearance	Colorless crystals
Melting point	262 °C (504 °F; 535 K)
Structure
Crystal structure	Monoclinic
Space group	Cc
Lattice constant	a = 15.410 Å, b = 9.4020 Å, c = 11.0930 Å α = 90°, β = 124.235°, γ = 90°
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

The anthracene–maleic anhydride adduct is an organic compound and an example of a Diels–Alder adduct. It is commonly prepared in organic chemistry teaching laboratories as an example of the Diels–Alder reaction.^[2]^[4]

Preparation

The anthracene–maleic anhydride adduct may be prepared by the reaction of equimolar amounts of anthracene and maleic anhydride in refluxing xylenes:^[3]

The product crystallizes from the reaction mixture upon cooling.

References

^ "Anthracene-maleic anhydride Diels-Alder adduct". webbook.nist.gov. NIST Office of Data and Informatics. Retrieved 2025-05-23.
^ ^a ^b Jasperse, Craig. "Diels-Alder Reaction" (PDF). Jasperse Chem 355 Syllabus. Minnesota State University Moorhead. Retrieved 23 May 2025.
^ ^a ^b ^c ^d Díaz de Delgado, Graciela; Ramírez V, Belkis; Velásquez, William; Rodríguez, Pedro (2002-05-15). "A new polymorph of 9,10-dihydroanthracene-9,10-α,β-succinic acid anhydride". Acta Crystallographica Section E: Structure Reports Online. 58 (5): o501 – o503. Bibcode:2002AcCrE..58O.501D. doi:10.1107/S1600536802005767. ISSN 1600-5368.
^ Amin, Shikha; Barnes, Ashley; Buckner, Courtney; Jones, Jordan; Monroe, Mattie; Nurmomade, Leon; Pinto, Taylor; Starkey, Samuel; Agee, Brian M.; Crouse, David J.; Swartling, Daniel J. (2015-04-14). "Diels–Alder Reaction Using a Solar Irradiation Heat Source Designed for Undergraduate Organic Chemistry Laboratories". Journal of Chemical Education. 92 (4): 767–770. Bibcode:2015JChEd..92..767A. doi:10.1021/ed500850c. ISSN 0021-9584.

[1] "Anthracene-maleic anhydride Diels-Alder adduct". webbook.nist.gov. NIST Office of Data and Informatics. Retrieved 2025-05-23.

[jasperse-2] Jasperse, Craig. "Diels-Alder Reaction" (PDF). Jasperse Chem 355 Syllabus. Minnesota State University Moorhead. Retrieved 23 May 2025.

[iucr-3] Díaz de Delgado, Graciela; Ramírez V, Belkis; Velásquez, William; Rodríguez, Pedro (2002-05-15). "A new polymorph of 9,10-dihydroanthracene-9,10-α,β-succinic acid anhydride". Acta Crystallographica Section E: Structure Reports Online. 58 (5): o501 – o503. Bibcode:2002AcCrE..58O.501D. doi:10.1107/S1600536802005767. ISSN 1600-5368.

[4] Amin, Shikha; Barnes, Ashley; Buckner, Courtney; Jones, Jordan; Monroe, Mattie; Nurmomade, Leon; Pinto, Taylor; Starkey, Samuel; Agee, Brian M.; Crouse, David J.; Swartling, Daniel J. (2015-04-14). "Diels–Alder Reaction Using a Solar Irradiation Heat Source Designed for Undergraduate Organic Chemistry Laboratories". Journal of Chemical Education. 92 (4): 767–770. Bibcode:2015JChEd..92..767A. doi:10.1021/ed500850c. ISSN 0021-9584.

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