128140-82-9

Basic information

• Product Name: 4-(DIFLUOROMETHOXY)IODOBENZENE
• Synonyms: 4-(DIFLUOROMETHOXY)IODOBENZENE;1-(Difluoromethoxy)-4-iodobenzene;4-(Difluoromethoxy)iodobenzene 98%;4-(Difluoromethoxy)iodobenzene98%;4-(Difluoromethoxy)-1-iodobenzene;4-Iodo-1-(difluoroMethoxy)benzene;1-(Difluoromethoxy)-4-iodobenzene98%
• CAS NO: 128140-82-9
• Molecular Formula: C₇H₅F₂IO
• Molecular Weight: 270.02
• Product Categories: Anisoles, Alkyloxy Compounds & Phenylacetates;Fluorine Compounds;Iodine Compounds
• Mol File: 128140-82-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 217-219 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.871 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.548(lit.)
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 4-(DIFLUOROMETHOXY)IODOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(DIFLUOROMETHOXY)IODOBENZENE(128140-82-9)
• EPA Substance Registry System: 4-(DIFLUOROMETHOXY)IODOBENZENE(128140-82-9)

Safety Data

• Hazard Codes: Xi
• Statements: 38
• Safety Statements: 37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 128140-82-9(Hazardous Substances Data)

Usage

General Description

4-(Difluoromethoxy)iodobenzene is a chemical compound with the molecular formula C7H5F2IO. It is a pale yellow solid that is commonly used in organic synthesis as a reagent and intermediate for the production of pharmaceuticals and other fine chemicals. 4-(Difluoromethoxy)iodobenzene is known for its ability to undergo various chemical reactions, such as halogenation, arylation, and cross-coupling, making it a versatile building block for the synthesis of complex organic molecules. Additionally, its unique structure and properties make it valuable in the field of medicinal chemistry and drug discovery. Overall, 4-(Difluoromethoxy)iodobenzene is an important chemical reagent with a wide range of applications in organic synthesis and pharmaceutical development.

Upstream product

• 22236-10-8 4-difluoromethoxyaniline 
• 5905-69-1 1-bromo-4-(difluoromethoxy)benzene 
• 354-08-5 bromodifluoroacetic acid 
• 540-38-5 p-Iodophenol 
• 1885-46-7 trifluoromethanesulfonic acid difluoromethyl ether 
• 1190956-19-4 difluoromethyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate 
• 403496-62-8 p-chlorophenyl chlorodifluoromethyl sulfone 
• 930836-30-9 (chlorodifluoromethylsulfonyl)benzene 
• 384-67-8 2-chloro-2,2-difluoroacetophenone 
• 75-45-6 Chlorodifluoromethane 

Downstream Products

• 887757-48-4 2-(4-(difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1590409-42-9 C₂₀H₁₈F₂N₄O₂ 
• 22236-10-8 4-difluoromethoxyaniline 
• 1217131-54-8 diacetoxyiodo-4-difluoromethoxybenzene 
• 1065169-09-6 1-bromo-3-((4-(difluoromethoxy)phenyl)ethynyl)benzene 
• 1065169-77-8 4-((4-(difluoromethoxy)phenyl)ethynyl)-2-(3,3-difluoropropoxy)-1-fluorobenzene 
• 1065168-39-9 [3-(4-difluoromethoxy-phenylethynyl)-phenyl]-carbamic acid tert-butyl ester 
• 1065169-12-1 1-((4-(difluoromethoxy)phenyl)ethynyl)-3-methylbenzene 
• 931430-26-1 3-((4-(difluoromethoxy)phenyl)ethynyl)phenol 
• 918487-36-2 {[4-(difluoromethoxy)-phenyl]ethynyl}(trimethyl)silane 
• 922497-19-6 1-{[4-(difluoromethoxy)phenyl]ethynyl}adamantane 

Relevant articles and documents

Glycosyl Cross-Coupling with Diaryliodonium Salts: Access to Aryl C -Glycosides of Biomedical Relevance

A stereospecific cross-coupling reaction of anomeric nucleophiles with diaryliodonium triflates resulting in the synthesis of aryl C-glycosides is reported. This process capitalizes on a stereoretentive reaction of configurationally stable C1 stannanes and is promoted by a palladium catalyst in the presence of a bulky phosphine ligand that suppresses the undesired β-elimination. The utility of this reaction has been demonstrated in the preparation of a series of C-glycosides derived from common saccharides resulting in exclusive transfer of anomeric configuration from the anomeric nucleophile to the product, and in the synthesis of empagliflozin, a commercial antidiabetic drug.

Decarboxylative Trifluoromethylating Reagent [Cu(O2CCF3)(phen)] and Difluorocarbene Precursor [Cu(phen)2][O2CCF2Cl]

This article describes the new economic decarboxylative trifluoromethylating reagent [Cu(phen)(O2CCF3)] (1; phen=1,10-phenanthroline) and the efficient difluorocarbene precursor [Cu(phen)2][O2CCF2Cl] (2). Treatment of copper tert-butoxide with phen and subsequent addition of trifluoroacetic acid or chlorodifluoroacetic acid afforded air-stable complexes 1 and 2, respectively, which were characterized by X-ray crystallography. The copper(I) ion in 1 is coordinated by a bidentate phen ligand, a monodentate trifluoroacetate group, and a molecule of CH3CN in a distorted tetrahedral coordination geometry. The molecular structure of 2 adopts an ionic form that consists of a [Cu(phen)2]+ cation and a chlorodifluoroacetate anion. Complex 1 reacted with a variety of aryl and heteroaryl halides to form trifluoromethyl (hetero)arenes in good yields. The corresponding Hammett plot exhibited a linear relationship and a reaction parameter (ρ)=+0.56±0.02, which indicated that the trifluoromethylation reaction proceeded via a nucleophilic reactive species. Complex 2 reacts with phenols to produce aryl difluoromethyl ethers in modest-to-excellent yields. Mechanistic investigations revealed that the difluoromethylation reaction proceeds by initial copper-mediated formation of difluorocarbene and subsequent concerted addition of difluorocarbene to the phenol to form a three-center transition state.

SYNTHESIS OF DIFLUOROMETHYL ETHERS AND SULFIDES

The synthesis of difluoromethyl ethers and sulfides with a simple, non-ozone- depleting reagent is described. The difluoromethylation of phenols with this reagent occurs at room temperature within minutes with exceptional functional group tolerance. The mild conditions makes possible tandem processes for the conversion of aryl boronic acids, aryl halides and arenes to difluoromethyl ethers. Mechanistic studies support a reaction pathway involving nucleophilic attack of the phenolate to difluorocarbene.