Magnesium monoperoxyphthalate

Last updated
Magnesium monoperoxyphthalate
Magnesium monoperoxyphthalate.svg
Names
Preferred IUPAC name
Magnesium bis(2-carbonoperoxoylbenzoate)
Other names
H48; MMPP
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.071.808 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 279-013-0
PubChem CID
UNII
  • InChI=1S/2C8H6O5.Mg/c2*9-7(10)5-3-1-2-4-6(5)8(11)13-12;/h2*1-4,12H,(H,9,10);/q;;+2/p-2
    Key: PIOZZBNFRIZETM-UHFFFAOYSA-L
  • [Mg++].OOC(=O)C1=CC=CC=C1C([O-])=O.OOC(=O)C1=CC=CC=C1C([O-])=O
Properties
C16H10MgO10
Molar mass 386.551 g·mol−1
Hazards
Flash point 173.4 °C (344.1 °F; 446.5 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Magnesium monoperoxyphthalate (MMPP) is a water-soluble peroxy acid used as an oxidant in organic synthesis. Its main areas of use are the conversion of ketones to esters (Baeyer-Villiger oxidation), epoxidation of alkenes (Prilezhaev reaction), oxidation of sulfides to sulfoxides and sulfones, oxidation of amines to produce amine oxides, and in the oxidative cleavage of hydrazones. [1]

Due to its insolubility in non-polar solvents MMPP has seen less use than the more widely used meta-chloroperoxybenzoic acid (mCPBA). Although work up procedures are more simply handled in polar solvents, usage of MMPP to oxidize nonpolar substrates in biphasic media combined with a phase transfer catalyst have been inefficient. [1] Despite this MMPP has certain advantages over mCPBA including a lower cost of production and increased stability. [1]

MMPP is also used as the active ingredient in certain surface disinfectants such as Dismozon Pur. [2] As a surface disinfectant MMPP exhibits a broad spectrum biocidal effect including inactivation of endospores. [3] Its wide surface compatibility enables its use on sensitive materials, such as plastic and rubber equipment used in hospitals. Additionally MMPP has been investigated as a potential antibacterial agent for mouthwashes and toothpaste. [4]

References

  1. 1 2 3 Carvalho, João F.S.; Silva, M. Manuel Cruz; Sá e Melo, M. Luisa (2009). "Highly efficient epoxidation of unsaturated steroids using magnesium bis(monoperoxyphthalate) hexahydrate". Tetrahedron. 65 (14): 2773–81. doi:10.1016/j.tet.2009.01.100.
  2. ↑ "Magnesium Monoperoxyphthalate". ndrugs. Retrieved 19 December 2013.
  3. ↑ Baldry, M.G.C. (1984). "The antimicrobial properties of magnesium monoperoxyphthalate hexahydrate". Journal of Applied Bacteriology. 57 (3): 499–503. doi:10.1111/j.1365-2672.1984.tb01416.x. PMID   6397460.
  4. ↑ Scully, Crispian; El-Kabir, Mohamed; Greenman, John; Porter, Stephen R.; Mutlu, Serdar; Barton, Ian; Adair, Richard (1999). "The effects of mouth rinses and dentifrice-containing magnesium monoperoxyphthalate (mmpp) on oral microflora, plaque reduction, and mucosa". Journal of Clinical Periodontology. 26 (4): 234–8. doi:10.1034/j.1600-051X.1999.260406.x. PMID   10223394.
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