1,1-bis(acetyloxy)-3-oxo-3H-5,2-benziodaoxol-1-yl acetate

EN300-66581

Product class

Building Blocks

CAS number

87413-09-0

MW

424.14

Purity

95%

Stock Availability

EU, US, DE, UA

Lead time

1-5 days delivery time

Oxidizing reagent

The Dess-Martin reagent is a widely utilized oxidant, effectively transforming 1° and 2° alcohols into aldehydes and ketones. Presenting as a stable white powder, it exhibits a melting point ranging from 103 to 133 ℃[1]. The Dess-Martin reagent offers key advantages over chromium- and DMSO-based oxidants. These benefits encompass milder reaction conditions (at room temperature and neutral pH), abbreviated reaction times, elevated yields, simplified purification steps, exceptional chemoselectivity, and compatibility with sensitive functional groups[2]. Usually, the reaction is conducted in DCM or chloroform but can be performed in DMSO, DMF, and EtOAc. Using the standard Dess–Martin periodinane conditions, alcohols can be oxidized to aldehydes/ketones without affecting furan rings, sulfides, vinyl ethers, and secondary amides[1], [2]. Allylic alcohols, which are typically difficult to convert to their respective carbonyls using the typical oxidants, are easily oxidized using DMP. Also, it can oxidize N-protected amino alcohols without epimerization (unlike most other oxidants, including Swern oxidation).

Synonyms: Dess-Martin reagent; Dess-Martin Periodinane reagent; or Dess-Martin oxidant; 1,2-Benziodoxol-3(1H)-one; 1,1,1-tris(acetyloxy)-1,1-dihydro- (9CI); (1,1-Diacetoxy-3-oxo-1,2-benziodoxol-1-yl) acetate; 1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one; 1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-on; 3-Oxo-1λ5,2-benziodoxole-1,1,1(3H)-triyl triacetate

1,1,1-Triacetoxy-1,1-Dihydro-1,2-Benziodoxol-3(1 H )-One. Boeckman R. J.; George K. M. Encyclopedia of Reagents for Organic Synthesis 2009. DOI: 10.1002/047084289X.rt157m.pub2 2. Dess-Martin reagent. Wang Z. Comprehensive Organic Name Reactions and Reagents 2010. DOI: 10.1002/9780470638859

Name:

1,1-bis(acetyloxy)-3-oxo-3H-5,2-benziodaoxol-1-yl acetate

SMILES:

CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)C2=CC=CC=C21

CAS number:

87413-09-0

CLogP:

2.932

ACD number:

MFCD00130127

Dangerous good:

Yes

Class:

Aryl Halides

Formula:

C₁₃H₁₃IO₈

Subclass:

Aryl Halides, Aryl Halides for Pd-catalyzed Couplings, Aryl halides amenable to aromatic nucleophilic substitution, Aryl Iodides

MW:

424.14

Product class:

Building Blocks