2,3-Dimethylmaleic anhydride

2,3-Dimethylmaleic anhydride
Names
	Preferred IUPAC name 2,3-Dimethylfuran-2,5-dione
	Other names DMMA
Identifiers
CAS Number	766-39-2;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:182178;
ChEMBL	ChEMBL2270559;
ChemSpider	12469;
ECHA InfoCard	100.011.059
EC Number	212-165-8;
PubChem CID	13010;
UNII	6PP3N541QA;
CompTox Dashboard (EPA)	DTXSID6061103 ;
	InChI InChI=1S/C6H6O3/c1-3-4(2)6(8)9-5(3)7/h1-2H3 Key: MFGALGYVFGDXIX-UHFFFAOYSA-N;
	SMILES CC1=C(C(=O)OC1=O)C;
Properties
Chemical formula	C6H6O3
Molar mass	126.111 g·mol−1
Appearance	Colorless solid
Density	1.107 g/cm3
Melting point	96 °C (205 °F; 369 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2,3-Dimethylmaleic anhydride is an organic compound with the formula (CH₃)₂C₂(CO)₂O.^[1] It is related to maleic anhydride (MA) by replacement of the two CH units with CCH₃ groups. It is the anhydride of 2,3-dimethylmaleic acid.

Synthesis

The compound can be prepared from two equivalents of MA in the presence of various amines, such as 2-aminopyridine, followed by treatment with sulfuric acid.^[2]^[3] It has been evaluated as a comonomer.^[4] It occurs in some plants such as Colocasia esculenta.

References

^ Argade, Narshinha; Deore, Prashant; Haval, Kishan; Gadre, Smita (2014). "A Concise Account of the Chemistry of Valuable Alkyl(methyl)maleic Anhydrides". Synthesis. 46 (20): 2683–2700. doi:10.1055/s-0034-1378665.
^ ^a ^b Baumann, Marcus E.; Bosshard, Hans; Breitenstein, Werner; Rihs, Grety; Winkler, Tammo (1984). "Mechanismus der decarboxylativen Dimerisierung von Maleinsäureanhydrid zu Dimethylmaleinsäureanhydrid unter Einfluss von 2-Aminopyridin". Helvetica Chimica Acta. 67 (7): 1897–1905. doi:10.1002/hlca.19840670728.
^ Hood, David K. (2024). "Maleic Anhydride, Maleic Acid, and Fumaric Acid". Kirk-Othmer Encyclopedia of Chemical Technology. pp. 1–51. doi:10.1002/0471238961.1301120506051220.a01.pub3. ISBN 978-0-471-48494-3.
^ Florianczyk, T.; Sullivan, C.; Janovic, Z.; Vogl, O. (1981). "Alternating copolymers of dimethylmaleic anhydride". Polymer Bulletin. 5–5 (9–10). doi:10.1007/BF00254359.

[1] Argade, Narshinha; Deore, Prashant; Haval, Kishan; Gadre, Smita (2014). "A Concise Account of the Chemistry of Valuable Alkyl(methyl)maleic Anhydrides". Synthesis. 46 (20): 2683–2700. doi:10.1055/s-0034-1378665.

[Helv-2] Baumann, Marcus E.; Bosshard, Hans; Breitenstein, Werner; Rihs, Grety; Winkler, Tammo (1984). "Mechanismus der decarboxylativen Dimerisierung von Maleinsäureanhydrid zu Dimethylmaleinsäureanhydrid unter Einfluss von 2-Aminopyridin". Helvetica Chimica Acta. 67 (7): 1897–1905. doi:10.1002/hlca.19840670728.

[3] Hood, David K. (2024). "Maleic Anhydride, Maleic Acid, and Fumaric Acid". Kirk-Othmer Encyclopedia of Chemical Technology. pp. 1–51. doi:10.1002/0471238961.1301120506051220.a01.pub3. ISBN 978-0-471-48494-3.

[4] Florianczyk, T.; Sullivan, C.; Janovic, Z.; Vogl, O. (1981). "Alternating copolymers of dimethylmaleic anhydride". Polymer Bulletin. 5–5 (9–10). doi:10.1007/BF00254359.

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