2252-44-0 | 3-(Trifluoromethoxy)bromobenzene

CAS:2252-44-0 | 3-(Trifluoromethoxy)bromobenzene,Description

Synthesis Analysis

The synthesis of 1-Bromo-3-(trifluoromethoxy)benzene and its derivatives involves selective preparation methods, such as the treatment of bis(fluoromethyl)benzene with dibromo compounds in acidic media. These methods allow for the formation of synthetically useful intermediates like phenylmagnesium, -lithium, and -copper, which are pivotal in further chemical reactions (Porwisiak & Schlosser, 1996).

Molecular Structure Analysis

The molecular structure of 1-Bromo-3-(trifluoromethoxy)benzene and related compounds has been extensively studied through X-ray structure determinations. These studies have highlighted the presence of various interactions such as C–H···Br, C–Br···Br, and C–Br···π interactions, which play significant roles in the packing motifs of these compounds. Despite their close chemical similarity, these compounds exhibit highly variable packing motifs, demonstrating the complexity of their structural characteristics (Jones, Kuś, & Dix, 2012).

Chemical Reactions and Properties

1-Bromo-3-(trifluoromethoxy)benzene undergoes various chemical reactions, including treatment with lithium diisopropylamide (LDA) to generate phenyllithium intermediates, which can be trapped and further manipulated to produce diverse compounds. These reactions open pathways to the synthesis of naphthalenes and their derivatives, demonstrating the compound's utility in complex organic synthesis (Schlosser & Castagnetti, 2001).

Physical Properties Analysis

The physical properties of 1-Bromo-3-(trifluoromethoxy)benzene derivatives have been characterized by various techniques, including NMR, IR, and XRD. These studies have provided insights into the steric configurations of these molecules, which influence their intermolecular interactions and packing in the solid state. Such analyses are crucial for understanding the material's properties and potential applications in fields like fluorescence and photoluminescence (Zuo-qi, 2015).

Scientific Research Applications

Application 1: Preparation of 1,2-dehydro-3-(trifluoromethoxy)benzene 

• Summary of the Application : 1-Bromo-3-(trifluoromethoxy)benzene is used in the preparation of 1,2-dehydro-3-(trifluoromethoxy)benzene. This compound could be used as a building block in the synthesis of various organic compounds.
• Results or Outcomes : The outcome of this application is the production of 1,2-dehydro-3-(trifluoromethoxy)benzene. The yield and purity of the product would depend on the specific experimental conditions.

Application 2: Synthesis of Atropisomeric Diphosphine Ligand 

• Summary of the Application : 1-Bromo-3-(trifluoromethoxy)benzene is used in the synthesis of a new electronically deficient atropisomeric diphosphine ligand, (S)-CF3O-BiPhep [2,2′-bis(diphenylphosphino)-6,6′-ditrifluoromethoxy-1,1′-biphenyl].
• Results or Outcomes : The outcome of this application is the production of the atropisomeric diphosphine ligand. The yield and purity of the product would depend on the specific experimental conditions.

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