274623
Dess-Martin periodinane
97%
동의어(들):
1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one
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제품정보 (DICE 배송 시 비용 별도)
실험식(Hill 표기법):
C13H13IO8
CAS 번호:
Molecular Weight:
424.14
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
Assay:
97%
Quality Level
assay
97%
reaction suitability
reagent type: oxidant
mp
130-133 °C (lit.)
functional group
iodo
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
signalword
Danger
hcodes
Hazard Classifications
Eye Irrit. 2 - Self-react. C - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
supp_hazards
저장 등급
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
문서
Dess-Martin Periodinane enables mild oxidation of alcohols to aldehydes and ketones suitable for synthesizing complex intermediates.
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