83170-17-6

Basic information

• Product Name: Benzene, (bromodifluoromethyl)-
• CAS NO: 83170-17-6
• Molecular Formula: C7H5BrF2
• Molecular Weight: 207.018
• Mol File: 83170-17-6.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: Benzene, (bromodifluoromethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, (bromodifluoromethyl)-(83170-17-6)
• EPA Substance Registry System: Benzene, (bromodifluoromethyl)-(83170-17-6)

Safety Data

• Hazardous Substances Data: 83170-17-6(Hazardous Substances Data)

Upstream product

• 98-08-8 α,α,α-trifluorotoluene 
• 1078-58-6 diphenylzinc 
• 100-39-0 benzyl bromide 
• 4855-02-1 benzyl trifluoromethyl sulfone 
• 591-50-4 iodobenzene 
• 2248-46-6 ethyl 2,2-difluoro-2-phenylacetate 
• 360-03-2 2,2-Difluoro-2-phenylacetic acid 
• 100-52-7 benzaldehyde 
• 2785-29-7 benzyl potassium 
• 455-31-2 difluoromethylbenzene 

Downstream Products

• 882869-58-1 methyl 4,4-difluoro-4-phenylbutanoate 
• 1188475-59-3 C₁₃H₁₆F₂O₆ 
• 1188523-03-6 C₄₁H₃₉F₃O₅ 
• 1188523-01-4 C₄₁H₃₉ClF₂O₅ 
• 1188522-99-7 C₄₁H₃₉BrF₂O₅ 

Relevant articles and documents

Synthesis of ArCF2X and [18F]Ar-CF3via Cleavage of the Trifluoromethylsulfonyl Group

A versatile synthesis of ArCF2X and [18F]Ar-CF3 type compounds from readily available ArCF2SO2CF3 has been developed. Diverse nucleophiles, including weak nucleophiles such as halides (18F-, Cl-, Br-, and I-), RSH, and ROH, could react with ArCF2SO2CF3 efficiently to give the corresponding difluoromethylene products. The control experiments and the Hammett plot indicated that the reaction might proceed through a difluorocarbocation intermediate generated from the steric hindrance-assisted cleavage of the trifluoromethylsulfonyl group.

Iron-Catalyzed Halogen Exchange of Trifluoromethyl Arenes**

The facile production of ArCF2X and ArCX3 from ArCF3 using catalytic iron(III)halides is reported, which constitutes the first iron-catalyzed halogen exchange for non-aromatic C?F bonds. Theoretical calculations suggest direct activation of C?F bonds by iron coordination. ArCX3 and ArCF2X products of the reaction are synthetically valuable due to their diversification potential. In particular, chloro- and bromodifluoromethyl arenes (ArCF2Cl, ArCF2Br respectively) provide access to a myriad of difluoromethyl arene derivatives (ArCF2R). To optimize for mono-halogen exchange, a statistical method called Design of Experiments was used. Optimized parameters were successfully applied to electron rich and electron deficient aromatic substrates, and to the late stage diversification of flufenoxuron, a commercial insecticide. These methods are highly practical, being run at convenient temperatures and using inexpensive common reagents.

The Difluoromethyl Group as a Masked Nucleophile: A Lewis Acid/Base Approach

The difluoromethyl group (R-CF2H) imparts desirable pharmacokinetic properties to drug molecules and is commonly targeted as a terminal functional group that is not amenable to further modification. Deprotonation of widely available Ar-CF2