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274623

Sigma-Aldrich

Dess-Martin periodinane

97%

Synonym(s):

1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one

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About This Item

Empirical Formula (Hill Notation):
C13H13IO8
CAS Number:
87413-09-0
Molecular Weight:
424.14
MDL number:
MFCD00130127
UNSPSC Code:
12352005
PubChem Substance ID:
24856593
NACRES:
NA.22

Quality Level

100

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

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

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H242,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Self-react. C - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH044

Storage Class Code

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Articles

Dess–Martin Periodinane

Dess-Martin Periodinane enables mild oxidation of alcohols to aldehydes and ketones suitable for synthesizing complex intermediates.

Dess–Martin Periodinane

Dess-Martin Periodinane enables mild oxidation of alcohols to aldehydes and ketones suitable for synthesizing complex intermediates.

Dess–Martin Periodinane

Dess-Martin Periodinane enables mild oxidation of alcohols to aldehydes and ketones suitable for synthesizing complex intermediates.

Dess–Martin Periodinane

Dess-Martin Periodinane enables mild oxidation of alcohols to aldehydes and ketones suitable for synthesizing complex intermediates.

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