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Dess-Martin periodinane

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Dess-Martin periodinane Basic information
Product Name:Dess-Martin periodinane
Synonyms:Dess-Martin periodinane,D M P, TAPI;dess-martin periodinate;1,1,1-Triacetoxy-1,2-benziodoxole-IV-3(1H)-one;1,1,1-Triacetoxy-1,3-dihydro-3-oxo-1,2-benziodoxole-IV;1,1,1-Triacetoxy-3H-1,2-benziodoxole-IV-3-one;Martin's reagent;1,1-Dihydro-1,1,1-triacetoxy-1,2-benzoiodooxol-3(1H)-one (Dess-M;Dess-Martin periodinane solution
CAS:87413-09-0
MF:C13H13IO8
MW:424.14
EINECS:672-328-8
Product Categories:Hypervalent Iodine;Synthetic Reagents;Hypervalent Iodine Compounds;Oxidation;Synthetic Organic Chemistry;Fused Ring Systems
Mol File:87413-09-0.mol
Dess-Martin periodinane Structure
Dess-Martin periodinane Chemical Properties
Melting point 130-133 °C (lit.)
Boiling point 40 °C
density 1.369 g/mL at 25 °C
Fp >221 °F
storage temp. -20°C
solubility Soluble in chloroform, acetone, acetonitrile and methylene chloride. Slightly soluble in ether and hexane.
form Liquid
color Colorless to light yellow
Sensitive Light Sensitive
Merck 14,2933
BRN 4548207
Stability:Light Sensitive
InChIInChI=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
InChIKeyNKLCNNUWBJBICK-UHFFFAOYSA-N
SMILESI1(OC(=O)C)(OC(=O)C)(OC(=O)C)OC(=O)C2C=CC=CC1=2
CAS DataBase Reference87413-09-0(CAS DataBase Reference)
Safety Information
Hazard Codes Xn,O,Xi
Risk Statements 22-36/37/38-40-8-20/21/22-44
Safety Statements 26-36-36/37-24/25-23-17-45-36/37/39
RIDADR UN 1593 6.1/PG 3
WGK Germany 3
Hazard Note Harmful/Light sensitive
TSCA No
HazardClass 5.1
PackingGroup 
HS Code 29349990
MSDS Information
ProviderLanguage
(1,1,1-Triacetoxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one English
SigmaAldrich English
ACROS English
ALFA English
Dess-Martin periodinane Usage And Synthesis
DescriptionDess-Martin periodinane (DMP) is a hypervalent iodine compound widely used as a mild reagent for the oxidation of primary/secondary alcohols to aldehydes/ketones; oxidation of amides into imides; the dehydrogenation of amines to nitriles, and disulfides to sulfones. It is also used to selectively oxidize alkenes to epoxides. This is a useful reaction for generating three-membered cyclic ethers. Additionally, DMP is used to oxidatively cleave 1,2-diols to form aldehydes or ketones and in the synthesis of lactones.
Chemical PropertiesWhite Crystalline powder
UsesDess-Martin Periodinaneis a very usefulreagent used in the oxidation of primary alcohols to aldehydes and secondary alcohols to ketones.
UsesOxidizing reagent.
UsesDess Martin periodinane is used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones. It is also used as an oxidant for complexes with multifunctional alcohols. It is actively involved in the oxidation of N-protected-amino alcohols without epimerization and allylic alcohols.
reaction suitabilityreagent type: oxidant
Advantages Benefits of using Dess-Martin periodinane (DMP) as an oxidizing reagent:
milder reaction conditions (room temperature, neutral pH)
shorter reaction times and higher yields
high chemoselectivity
tolerance of sensitive functional groups, and a long shelf life
simplified workups
Tag:Dess-Martin periodinane(87413-09-0) Related Product Information
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