1208076-28-1 | 5-Bromo-2-(trifluoromethyl)benzonitrile

CAS:1208076-28-1 | 5-Bromo-2-(trifluoromethyl)benzonitrile,Description

5-Bromo-2-(trifluoromethyl)benzonitrile is a chemical compound with the molecular formula C8H3BrF3N and a molecular weight of 250.02. It is used for research and development purposes.

Molecular Structure Analysis

The molecular structure of 5-Bromo-2-(trifluoromethyl)benzonitrile consists of a benzonitrile core with a bromine atom at the 5-position and a trifluoromethyl group at the 2-position. The InChI code for this compound is 1S/C8H3BrF3N/c9-6-1-2-7(8(10,11)12)5(3-6)4-13/h1-3H.

Physical And Chemical Properties Analysis

5-Bromo-2-(trifluoromethyl)benzonitrile has a predicted boiling point of 255.2±35.0 °C and a predicted density of 1.71±0.1 g/cm3.

Scientific Research Applications

• Pharmaceutical Chemistry

  • Application : Trifluoromethyl group-containing drugs have been approved by the FDA over the last 20 years. These drugs have been used for various diseases and disorders.
  • Method : The synthesis of these drugs involves incorporating the trifluoromethyl group into potential drug molecules.
  • Results : Over 50 percent of the best-selling drug molecules approved by the US Food and Drug Administration (FDA) contain fluorine.

• Organic Synthesis

  • Application : 2-(Trifluoromethyl)benzonitrile has been used in the synthesis of symmetrical N, N ′-alkylidine bisamides.
  • Method : This involves a reaction with tert-butyl acetate in the presence of sulfuric acid.
  • Results : The outcome of this process is the corresponding N-tert-butyl amides.

• Medicinal Chemistry

  • Application : Trifluoromethyl group-containing compounds have been used in the development of new drug molecules.
  • Method : The Shanghai Institute of Pharmaceutical Industry developed a synthetic method for pexidartinib that involves a central tandem Tsuji–Trost reaction and Heck coupling.
  • Results : This method has been used to synthesize potential drug molecules.

• Material Science

  • Application : Dihalogenated benzonitrile building blocks, similar to 5-Bromo-2-(trifluoromethyl)benzonitrile, have been used as precursors for the synthesis of Thermally Activated Delayed Fluorescence (TADF) dyes in OLED applications.
  • Method : The specific methods of application or experimental procedures would depend on the specific OLED application.
  • Results : The use of these building blocks has led to advancements in OLED technology.

• Antitumor and Anti-inflammatory Applications

  • Application : Dihalogenated benzonitrile building blocks, similar to 5-Bromo-2-(trifluoromethyl)benzonitrile, have been used as precursors for the synthesis of APIs in antitumor and anti-inflammatory applications.
  • Method : The ortho positioning of bromide and nitrile groups of 2-bromo-5-fluorobenzonitrile facilitates its synthesis into quinazolines.
  • Results : These quinazolines have been used in antitumor and anti-inflammatory applications.

• OLED Applications

  • Application : Dihalogenated benzonitrile building blocks, similar to 5-Bromo-2-(trifluoromethyl)benzonitrile, have been used as precursors for the synthesis of Thermally Activated Delayed Fluorescence (TADF) dyes in OLED applications.
  • Method : A TADF dye, named as 2-phenoxazine-5-acridine-benzonitrile, is synthesized from 2-bromo-5-fluorobenzonitrile with phenoxazines, carbazoles or acridan in a two-step reaction that includes nucleophilic aromatic substitution and Buchwald-Hartwig amination.
  • Results : The resulting OLED device shows a maximum current efficiency of 16.3 cdA -1, a maximum powder efficiency of 12.2 lmW -1 and an external quantum efficiency of 5%.

Safety And Hazards

This compound is classified under GHS07 for safety. The hazard statements associated with it are H315, H319, and H335, indicating that it can cause skin irritation, serious eye irritation, and may cause respiratory irritation. Precautionary measures include avoiding dust formation, not breathing in dust, vapor, mist, or gas, and not ingesting the compound.

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