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:
Molecular Weight:
424.14
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
Assay:
97%
Quality Segment
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
Storage Class
5.2 - Organic peroxides and self-reacting hazardous materials
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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