1680206-12-5

Basic information

• Product Name: (bipyridine)Cu^III(CF₃)₃
• CAS NO: 1680206-12-5
• Molecular Weight: 426.752
• Mol File: 1680206-12-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (bipyridine)Cu^III(CF₃)₃(CAS DataBase Reference)
• NIST Chemistry Reference: (bipyridine)Cu^III(CF₃)₃(1680206-12-5)
• EPA Substance Registry System: (bipyridine)Cu^III(CF₃)₃(1680206-12-5)

Safety Data

• Hazardous Substances Data: 1680206-12-5(Hazardous Substances Data)

Usage

Description

(bipyridine)CuIII(CF3)3 is a coordination complex that features a copper (III) ion coordinated with three trifluoromethyl (CF3) ligands and a bipyridine bidentate ligand. This complex is recognized for its high reactivity, which makes it a candidate for various applications in catalysis and organic synthesis. The trifluoromethyl groups enhance the stability and lipophilicity of the compound, while the bipyridine ligand contributes to its chelating properties and coordination geometry, making (bipyridine)CuIII(CF3)3 a complex with significant potential in chemical transformations.

Uses

Used in Catalysis:
(bipyridine)CuIII(CF3)3 is used as a catalyst in the chemical industry due to its high reactivity. The copper (III) center can facilitate various chemical reactions, making it a valuable component in the synthesis of complex organic molecules.
Used in Organic Synthesis:
In the field of organic chemistry, (bipyridine)CuIII(CF3)3 is utilized as a reagent for organic transformations. Its unique combination of ligands allows it to participate in a range of reactions, contributing to the formation of diverse organic compounds.
Used in Pharmaceutical Industry:
(bipyridine)CuIII(CF3)3 may also find applications in the pharmaceutical industry, where its coordination properties could be harnessed for the development of new drugs or drug delivery systems. (bipyridine)Cu^III(CF₃)₃'s ability to chelate with other molecules makes it a potential candidate for targeted drug delivery or as a component in medicinal chemistry.
Used in Material Science:
(bipyridine)Cu^III(CF₃)₃'s stability and lipophilicity suggest potential uses in material science, where it could be employed in the development of new materials with specific properties, such as improved conductivity or enhanced chemical resistance.

Upstream product

• 553-26-4 4,4'-bipyridine 
• 7681-65-4 copper(l) iodide 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 366-18-7 [2,2]bipyridinyl 
• 152376-94-8 ⁿBu₄N⁺[Cu(CF₃)₄]^- 

Downstream Products

• 3839-35-8 4-methylbenzenesulfonic acid n-hexylester 
• 50561-99-4 1-fluoro-4-(2,2,2-trifluoroethyl)benzene 
• 81577-07-3 1-chloro-4-(2,2,2-trifluoroethyl)benzene 
• 1099597-89-3 1-(tert-butyl)-4-(2,2,2-trifluoroethyl)benzene 
• 18880-00-7 1-(bromomethyl)-4-(1,1-dimethylethyl)benzene 
• 50562-01-1 1-methyl-4-(2,2,2-trifluoroethyl)benzene 
• 158884-40-3 1-Methyl-2-(2,2,2-trifluoroethyl)benzene 
• 50562-00-0 1-methyl-3-(2,2,2-trifluoroethyl)benzene 
• 21249-93-4 (2,2,2-trifluoroethyl)benzene 

Relevant articles and documents

Direct C(sp3)?H Trifluoromethylation of Unactivated Alkanes Enabled by Multifunctional Trifluoromethyl Copper Complexes

A mild and operationally simple C(sp3)?H trifluoromethylation method was developed for unactivated alkanes by utilizing a bench-stable CuIII complex, bpyCu(CF3)3, as the initiator of the visible-light photoinduced reaction, the source of a trifluoromethyl radical as a hydrogen atom transfer reagent, and the source of a trifluoromethyl anion for functionalization. The reaction was initiated by the generation of reactive electrophilic carbon-centered CF3 radical through photoinduced homolytic cleavage of bpyCu(CF3)3, followed by hydrogen abstraction from an unactivated C(sp3)?H bond. Comprehensive mechanistic investigations based on a combination of experimental and computational methods suggested that C?CF3 bond formation was enabled by radical–polar crossover and ionic coupling between the resulting carbocation intermediate and the anionic CF3 source. The methylene-selective reaction can be applied to the direct, late-stage trifluoromethylation of natural products and bioactive molecules.

Synthesis method of prodrug for Mycobacterium tuberculosis activity inhibitor

The invention provides a synthesis method of a prodrug for a Mycobacterium tuberculosis activity inhibitor. The method comprises the following steps: S1, adding acetic acid into a reactor A, sequentially adding cuprous chloride, bipyridine, trifluoromethyltrimethylsilane and potassium fluoride, carrying out a reaction, filtering the obtained solution to obtain a bright yellow solid, washing the bright yellow solid, and carrying out suction drying to obtain a bipyridine complex of trifluoromethy copper; and S2, adding the bipyridine complex of trifluoromethy copper, obtained in step S1, and a piperidine derivative into a reactor B, then adding triethylsilane, potassium persulfate, acetone and deionized water, carrying out a reaction at room temperature, carrying out reduced pressure rotaryevaporation to remove the solvent, washing the obtained crude product, concentrating the washed crude product, and recrystallizing the concentrated crude product to obtain the target product. The method has the advantages of low price and easy obtaining of raw materials, simplicity in reaction operation, obtaining of the trifluoromethyl product with high added values, realization of complete separation only by recrystallization, realization of the purity of the final product being 98% or above, and realization of amplified production by using water as a green solvent in the reaction and avoiding anhydrous and anaerobic harsh conditions.

Copper-Mediated Trifluoromethylation of Benzylic Csp3?H Bonds

Trifluoromethyl-containing compounds play a significant role in medicinal chemistry, materials and fine chemistry. Although direct C?H trifluoromethylation has been achieved on Csp2?H bonds, direct conversion of Csp3?H bonds to Csp3?CF3 remains challenging. We report herein an efficient protocol for the selective trifluoromethylation of benzylic C?H bonds. This process is mediated by a combination CuIII?CF3 species and persulfate salts. A wide range of methylarenes can be selectively trifluoromethylated at the benzylic positions. A combination of experimental and theoretical mechanistic studies suggests that the reaction involves a radical intermediate and a CuIII?CF3 species as the CF3 transfer reagent.