Substance
ID:737608
Names and Identifiers
IUPAC Traditional name
dess-martin periodinane
Synonyms
Dess-Martin periodinane1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-oneDMP戴斯-马丁试剂
IUPAC name
1,1-bis(acetyloxy)-3-oxo-3H-1λ5,2-benziodaoxol-1-yl acetate
Registration numbers
CAS Number
MDL Number
Merck Index
Beilstein Number
Properties
Safety Information
European Hazard Symbols
Irritant (Xi)
Oxidising (O)Risk Statements
8-36/37/38-44
Storage Warning
Moisture & Light Sensitive
UN Number
UN1479
Safety Statements
17-26-37
TSCA Listed
否
Hazard Class
5.1
GHS Pictograms
Acute toxicity (oral, dermal, inhalation), category 4
Skin irritation, category 2
Eye irritation, category 2
Skin sensitisation, category 1
Specific Target Organ Toxicity – Single exposure, category 3
Oxidizing gases, category 1
Oxidizing liquids, categories 1,2,3
GHS Hazard statements
H272-H315-H319-H335
Packing Group
III
GHS Precautionary statements
P221-P210-P305+P351+P338-P302+P352-P405-P501A
Physical Property
Melting Point
130-132°C dec.
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
• For use in the synthesis of imides, N-acyl vinylogous carbamates and ureas, and nitriles, by oxidation of amides and amines, see: Angew. Chem. Int. Ed., 44, 5992 (2005).
• Has also been used for deoximation of ketoximes to ketones under mild conditions: Tetrahedron Lett., 39, 3209 (1998); Synthesis, 760 (1999).
• Deprotection of thioacetals can be accomplished under extremely mild conditions: Org. Lett., 5, 575 (2003).
• ɑ,?-Unsaturated carboxylic acids undergo Hunsdiecker-type decaboxylative bromination with tetraethylammonium bromide in the presence of the reagent: Synlett, 2495 (2005).
• One of the mildest reagents for the selective oxidation of primary and secondary alcohols to aldehydes and ketones. High yields can be obtained at ambient temperatures, under neutral conditions, in chloroform, dichloromethane or acetonitrile: J. Org. Chem., 48, 4155 (1983); J. Am. Chem. Soc., 113, 7277 (1991); (reviews): J. Prakt. Chem./Chem. Ztg., 338, 588 (1996); Synlett, 278 (2000). Has been employed for the oxidation of a wide variety of sensitive substrates and is particularly valuable in multi-step syntheses of polyfunctional molecules with complex stereochemistry. For an example involving exclusive oxidation of one of four possible secondary OH groups in a synthesis of erythromycin B, see: J. Am. Chem. Soc., 119, 3193 (1997). Allylic and benzylic alcohols can be oxidized selectively in the presence of saturated alcohols, and give the carbonyl compounds cleanly without over-oxidation or cis-trans isomerization: Tetrahedron Lett., 29, 995 (1988); J. Org. Chem., 55, 1636 (1990).
• For a detailed discussion of the scope and advantages of this reagent, see: Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed., Wiley, Chichester (1995), vol. 7, p. 4982.
• Hydroxamic acids are oxidized to acyl nitroso compounds which can undergo cycloaddition to dienes: Synth. Commun., 30, 47 (2000).
• CAUTION! In the presence of moisture, may form iodoxybenzoic acid which has been reported to be explosive under excessive heating or impact: Chem. Eng. News, 68(29), 3 (1990).