Dess–Martin periodinane

Dess–Martin periodinane
Names
Preferred IUPAC name
3-Oxo-1λ5,2-benziodoxole-1,1,1(3H)-triyl triacetate
Other names
Dess–Martin periodinane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.197.885
UNII
  • InChI=1S/C13H13IO8/c1-8(15)19-14(20-9(2)16,21-10(3)17)12-7-5-4-6-11(12)13(18)22-14/h4-7H,1-3H3
    Key: NKLCNNUWBJBICK-UHFFFAOYSA-N
  • InChI=1S/C13H13IO8/c1-8(15)19-14(20-9(2)16,21-10(3)17)12-7-5-4-6-11(12)13(18)22-14/h4-7H,1-3H3
    Key: NKLCNNUWBJBICK-UHFFFAOYAQ
  • CC(=O)OI1(c2ccccc2C(=O)O1)(OC(=O)C)OC(=O)C
Properties
C13H13IO8
Molar mass 424.14 g/mol
Appearance white powder, chips,
crystals or crystalline
powder and/or chunks
Density 1.362 g/cm3 solid
Melting point 103 to 133 °C (217 to 271 °F; 376 to 406 K)
Related compounds
Related compounds
 2-Iodoxybenzoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dess–Martin periodinane (DMP) is a chemical reagent used in the Dess–Martin oxidation, oxidizing primary alcohols to aldehydes and secondary alcohols to ketones. This periodinane has several advantages over chromium- and DMSO-based oxidants that include milder conditions (room temperature, neutral pH), shorter reaction times, higher yields, simplified workups, high chemoselectivity, tolerance of sensitive functional groups, and a long shelf life. However, use on an industrial scale is made difficult by its cost and its potentially explosive nature. It is named after the American chemists Daniel Benjamin Dess and James Cullen Martin who developed the reagent in 1983. It is based on IBX, but due to the acetate groups attached to the central iodine atom, DMP is much more reactive than IBX and is much more soluble in organic solvents.

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