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Merck

274623

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
NACRES:
NA.22
PubChem Substance ID:
24856593
UNSPSC Code:
12352005
MDL number:
MFCD00130127
Assay:
97%

Key Documents

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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

SMILES string

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

InChI key

NKLCNNUWBJBICK-UHFFFAOYSA-N

assay

97%

reaction suitability

reagent type: oxidant

mp

130-133 °C (lit.)

functional group

iodo

storage temp.

−20°C

Quality Level

100

Related Categories

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

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.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

supp_hazards

EUH044

Storage Class

5.2 - Organic peroxides and self-reacting hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP7243
MKCP2798
MKCN7253
MKCL9464
MKCK3971

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Nan Wang et al.
BMC biotechnology, 16(1), 87-87 (2016-12-03)
Manganese peroxidase (MnP) from Irpex lacteus F17 has been shown to have a strong ability to degrade recalcitrant aromatic pollutants. In this study, a recombinant MnP from I. lacteus F17 was expressed in Escherichia coli Rosetta (DE3) in the form
Advanced Synthesis & Catalysis, 346, 111-124 (2004)
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
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
The Journal of Organic Chemistry, 48, 4155-4155 (1983)
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