274623

Dess-Martin periodinane

97%

• Synonym(s): 1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one
• Empirical Formula (Hill Notation): C₁₃H₁₃IO₈
• CAS Number: 87413-09-0
• Molecular Weight: 424.14
• MDL number: MFCD00130127
• UNSPSC Code: 12352005
• PubChem Substance ID: 24856593
• NACRES: NA.22

Properties

• Quality Level: 100
• 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

Description

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.[1]
• To synthesize alkynyl oxoaldehyde probe (AlkMGO). [2]

Used for the oxidation of hydroxychlorins to chlorin-α-diones and tetraones.[3]

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

Safety Information

• Pictograms: GHS02,GHS07
• Signal Word: Danger
• Hazard Statements: H242,H315,H319,H335
• Precautionary Statements: P210 - P235 - P302 + P352 - P305 + P351 + P338 - P370 + P378 - P403 + P233
• Hazard Classifications: Eye Irrit. 2 - Self-react. C - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Supplementary Hazards: EUH044
• Storage Class Code: 5.2 - Organic peroxides and self-reacting hazardous materials
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves