2902-68-3

Basic information

• Product Name: Iodosodilactone
• Synonyms: 2aλ3-Ioda-2,3-dioxa-cyclopenta[cd]indene-1,4-dione;2H,6H-[1,2]Iodoxolo[4,5,1-hi][1,2]benziodoxole-2,6-dione;Iodosodilactone
• CAS NO: 2902-68-3
• Molecular Formula: C₈H₃IO₄
• Molecular Weight: 290.01149
• Mol File: 2902-68-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 263°C(lit.)
• Appearance: /
• CAS DataBase Reference: Iodosodilactone(CAS DataBase Reference)
• NIST Chemistry Reference: Iodosodilactone(2902-68-3)
• EPA Substance Registry System: Iodosodilactone(2902-68-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 2902-68-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Iodosodilactone is used as a coupling reagent for various organic reactions, such as amidation, peptide coupling, and esterification. It facilitates the formation of amides, esters, peptides, and macrocyclic lactones without racemization, which is crucial for maintaining the desired stereochemistry of the target molecules.
Used in Oxidation Reactions:
In the field of arylation reactions, iodosodilactone serves as an effective oxidant, particularly for fluorophenols. Its ability to selectively oxidize substrates without causing over-oxidation or side reactions makes it a preferred choice for chemists working on the synthesis of aryl-containing compounds.

Upstream product

• 2902-65-0 2-iodoyl-1,3-benzenedicarboxylic acid 

Downstream Products

• 1381884-87-2 C₂₆H₁₈IO₄P 
• 1381884-54-3 di-2-phenylethyl 2-iodoisophthalate 
• 71653-43-5 2-phenylethyl nicotinate 

Relevant articles and documents

Regioselective Oxidative Arylation of Fluorophenols

A metal free and highly regioselective oxidative arylation reaction of fluorophenols is described. The relative position of the fluoride leaving group (i.e., ortho or para) controls the 1,2 or 1,4 nature of the arylated quinone product, lending versatilit

Recyclable hypervalent iodine(III) reagent iodosodilactone as an efficient coupling reagent for direct esterification, amidation, and peptide coupling

A hypervalent iodine(III) reagent plays a novel role as an efficient coupling reagent to promote the direct condensation between carboxylic acids and alcohols or amines to provide esters, macrocyclic lactones, amides, as well as peptides without racemization. The regeneration of iodosodilactone (1) can also be readily achieved. The intermediate acyloxyphosphonium ion C from the activation of a carboxylic acid is thought to be involved in the present esterification reaction.