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Methacrylic anhydride

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Methacrylic anhydride
Names
Preferred IUPAC name 2-Methylprop-2-enoic anhydride
Other names Methacrylic anhydride
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.986 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H10O3/c1-5(2)7(9)11-8(10)6(3)4/h1,3H2,2,4H3Key: DCUFMVPCXCSVNP-UHFFFAOYSA-N
  • InChI=1/C8H10O3/c1-5(2)7(9)11-8(10)6(3)4/h1,3H2,2,4H3Key: DCUFMVPCXCSVNP-UHFFFAOYAX
SMILES
  • O=C(OC(=O)\C(=C)C)\C(=C)C
Properties
Chemical formula C8H10O3
Molar mass 154.165 g·mol
Density 1.035 g/cm
Boiling point 87 °C/13 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Methacrylic anhydride is a liquid which reacts with water exothermically.

It can also react with hydroxyl and amino groups present in some organic compounds leading to covalent attachment of methacryloyl moieties. These functional groups could be successfully used either in subsequent polymerisation or reactions with thiols. For example, chitosan modified by methacryloylation exhibits better ability to adhere to mucosal surfaces (mucoadhesion) due to its reactivity with thiols groups present in cysteine domains of mucins.

Uses

Methacrylic anhydride is used as an intermediate agent in plastics, material, and resin manufacturing.

References

  1. Methacrylic anhydride at www.chemicalbook.com.
  2. Kolawole, Oluwadamilola M.; Lau, Wing Man; Khutoryanskiy, Vitaliy V. (2018-10-25). "Methacrylated chitosan as a polymer with enhanced mucoadhesive properties for transmucosal drug delivery" (PDF). International Journal of Pharmaceutics. 550 (1): 123–129. doi:10.1016/j.ijpharm.2018.08.034. ISSN 0378-5173. PMID 30130604. S2CID 52055140.
  3. "Methacrylic anhydride". PubChem. National Institute of Health. Retrieved 2023-01-20.
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