Skip to Content
Merck
CN
All Photos(5)

Documents

274623

Sigma-Aldrich

Dess-Martin periodinane

97%

Sign Into View Organizational & Contract Pricing
All Photos(5)
Synonym(s):
1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one
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

Related Categories

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
GHS03,GHS07

Signal Word

Danger

Hazard Statements

H272,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

The Journal of Organic Chemistry, 48, 4155-4155 (1983)
Brittany A Weldon et al.
Toxicology and applied pharmacology, 312, 19-25 (2016-01-31)
MicroRNAs (miRNAs) are post-transcriptional regulators that silence messenger RNAs. Because miRNAs are stable at room temperature and long-lived, they have been proposed as molecular biomarkers to monitor disease and exposure status. While urinary miRNAs have been used clinically as potential
Advanced Synthesis & Catalysis, 346, 111-124 (2004)
Synthesis of highly epimerizable N-protected $\alpha$-amino aldehydes of high enantiomeric excess
Andrew GM,et al.
Tetrahedron Letters, 41, 1359-1362 (2000)
Iman Al-Saleh et al.
The Science of the total environment, 578, 440-451 (2016-11-12)
Plasticizers such as phthalate esters (PAEs) and bisphenol A (BPA) are highly persistent organic pollutants that tend to bio-accumulate in humans through the soil-plant-animal food chain. Some studies have reported the potential carcinogenic and teratogenic effects in addition to their
View All Related Papers

Articles

Dess–Martin Periodinane

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service