Dess-Martin periodinane Chemical Properties

Melting point:

130-133 °C (lit.)

Boiling point:

40 °C

Density 

1.369 g/mL at 25 °C

Flash point:

>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

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

InChIKey

NKLCNNUWBJBICK-UHFFFAOYSA-N

SMILES

I1(OC(=O)C)(OC(=O)C)(OC(=O)C)OC(=O)C2C=CC=CC1=2

CAS DataBase Reference

87413-09-0(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 

Ⅲ

HS Code 

29349990

MSDS

• Language:English Provider:(1,1,1-Triacetoxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Dess-Martin periodinane Usage And Synthesis

Description

Dess-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 Properties

White Crystalline powder

Uses

Dess-Martin Periodinaneis a very usefulreagent used in the oxidation of primary alcohols to aldehydes and secondary alcohols to ketones.

Uses

Dess 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.

Uses

Oxidizing reagent.

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

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