87167-83-7

Basic information

• Product Name: 2-methylphenyliodine bis(trifluoroacetate)
• Synonyms: 2-methylphenyliodine bis(trifluoroacetate)
• CAS NO: 87167-83-7
• Molecular Weight: 444.069
• Mol File: 87167-83-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-methylphenyliodine bis(trifluoroacetate)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methylphenyliodine bis(trifluoroacetate)(87167-83-7)
• EPA Substance Registry System: 2-methylphenyliodine bis(trifluoroacetate)(87167-83-7)

Safety Data

• Hazardous Substances Data: 87167-83-7(Hazardous Substances Data)

Upstream product

• 615-37-2 ortho-methylphenyl iodide 
• 76-05-1 trifluoroacetic acid 
• 31599-59-4 2-(diacetoxyiodo)toluene 

Relevant articles and documents

Electrochemical-Induced Ring Transformation of Cyclic α-(ortho-Iodophenyl)-β-oxoesters

Cyclic α-(ortho-iodophenyl)-β-oxoesters were converted in a ring-expanding transformation to furnish benzannulated cycloalkanone carboxylic esters. The reaction sequence started by electrochemical reduction of the iodoarene moiety. In a mechanistic rationale, the resulting carbanionic species was adding to the carbonyl group under formation of a strained, tricyclic benzocyclobutene intermediate, which underwent carbon–carbon bond cleavage and rearrangement of the carbon skeleton by retro-aldol reaction. The scope of the reaction sequence was investigated by converting cyclic oxoesters with different ring sizes yielding benzocycloheptanone, -nonanone and -decanone derivatives in moderate to good yields. Furthermore, acyclic starting materials and cyclic compounds carrying additional substituents on the iodophenyl ring were submitted to this reaction sequence. The starting materials for this transformation are straightforwardly obtained by conversion of β-oxoesters with phenyliodobis(trifluoroacetate).

An Alternative to the Classical α-Arylation: The Transfer of an Intact 2-Iodoaryl from ArI(O2CCF3)2

The α-arylation of carbonyl compounds is generally accomplished under basic conditions, both under metal catalysis and via aryl transfer from the diaryl λ3-iodanes. Here, we describe an alternative metal-free α-arylation using ArI(O2CCF3)2 as the source of a 2-iodoaryl group. The reaction is applicable to activated ketones, such as α-cyanoketones, and works with substituted aryliodanes. This formal C-H functionalization reaction is thought to proceed through a [3,3] rearrangement of an iodonium enolate. The final α-(2-iodoaryl)ketones are versatile synthetic building blocks.