Dess–Martin periodinane

Dess–Martin periodinane

Names
IUPAC name 1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one
Other names Dess–Martin periodinane
Identifiers
CAS Number	87413-09-0
3D model (Jmol)	Interactive image
ChemSpider	139925
ECHA InfoCard	100.197.885
PubChem CID	159087
InChI 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
SMILES CC(=O)OI1(c2ccccc2C(=O)O1)(OC(=O)C)OC(=O)C
Properties
Chemical formula	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 to oxidize 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. 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.

The most friendly synthesis of IBX has been determined to be treating 2-iodobenzoic acid with oxone in water, at elevated temperatures for 3 hours. IBX is then acylated using Ireland and Liu’s modifications from the original procedure. These modifications allowed for higher yields and a simplified work up procedure. The resulted solids can be obtained via filtration and washing with ether. Ireland and Liu used a catalytic amount of tosylic acid, which allowed the reaction to complete in less than 2 hours (compared to the classic synthesis, utilizing 24 hours) and in yields exceeding 90%.

The classic method presented by Boeckman and Mullins involved heating a solution of potassium bromate, sulfuric acid, 2-iodobenzoic acid to afford IBX (1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide, 2-iodoxybenzoic acid). IBX was then acylated using acetic acid and acetic anhydride.