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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

Product Name

Dess-Martin periodinane, 97%

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
0000496553
0000496553
0000495561
0000495561
0000464579

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Hui Chen et al.
Environmental science and pollution research international, 26(24), 24609-24619 (2019-06-27)
Phthalates (PAEs) in drinking water sources such as the Yangtze River in developing countries had aroused widespread concern. Here, the water, suspended particulate matter (SPM), and sediment samples were collected from 15 sites in wet and dry seasons in Zhenjiang
Synthesis of an alkynyl methylglyoxal probe to investigate nonenzymatic histone glycation
Qingfei Z,et al.
The Journal of Organic Chemistry, 85, 1691-1697 (2019)
Jun Wang et al.
Journal of endodontics, 43(1), 109-115 (2016-11-17)
Mutations in the proteinase bone morphogenetic protein-1 (BMP1) were recently identified in patients with osteogenesis imperfecta, which can be associated with type 1 dentinogenesis imperfecta. BMP1 is co-expressed in various tissues and has overlapping activities with the closely related proteinase
The Journal of Organic Chemistry, 48, 4155-4155 (1983)
Synthesis of highly epimerizable N-protected $\alpha$-amino aldehydes of high enantiomeric excess
Andrew GM,et al.
Tetrahedron Letters, 41, 1359-1362 (2000)
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