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274623

Sigma-Aldrich

Dess-Martin periodinane

97%

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Synonym(s):
1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one
Empirical Formula (Hill Notation):
C13H13IO8
CAS Number:
Molecular Weight:
424.14
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

reaction suitability

reagent type: oxidant

mp

130-133 °C (lit.)

storage temp.

−20°C

SMILES string

CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc12

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

InChI key

NKLCNNUWBJBICK-UHFFFAOYSA-N

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This Item
559873696641394963
vibrant-m

274623

Dess-Martin periodinane

vibrant-m

559873

Dess-Martin periodinane solution

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

assay

97%

assay

-

assay

95%

assay

>95%

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

mp

130-133 °C (lit.)

mp

-

mp

75-79 °C

mp

-

General 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.

Application

Dess–Martin periodinane is used as an oxidizing agent:
  • For 1° and 2° alcohols to aldehydes and ketones.
  • In the synthesis of N-protected α-amino aldehydes from the corresponding N-protected β-amino alcohols.
  • To synthesize alkynyl oxoaldehyde probe (AlkMGO).
Used for the oxidation of hydroxychlorins to chlorin-α-diones and tetraones.

Features and Benefits

Benefits of using 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

pictograms

Flame over circleExclamation mark

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Ox. Sol. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

5.1B - Oxidizing hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Articles

Dess-Martin Periodinane is used for the mild oxidation of alcohols to aldehydes and ketones. The neutral condition of the reaction makes DMP suitable for syntheses of sensitive, functionally complex intermediates.

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