54962-75-3 | 3-Amino-5-bromobenzotrifluoride

CAS:54962-75-3 | 3-Amino-5-bromobenzotrifluoride,Description

3-Bromo-5-(trifluoromethyl)aniline is a chemical compound that has been the subject of various studies due to its potential applications in pharmaceuticals and as an intermediate in organic synthesis. The compound contains a bromine atom and a trifluoromethyl group attached to an aniline ring, which significantly influences its chemical behavior and properties.

Synthesis Analysis

The synthesis of related aniline derivatives has been explored in several studies. For instance, a method for the preparation of 2-bromo-1,1,2,2-tetrafluoroethyl arenes using anilines as starting materials has been developed, which demonstrates the potential for further modifications in the synthesis of functional molecules. Another study reports a transition metal-free method for the synthesis of meta-bromo- and meta-trifluoromethylanilines, showcasing the ability to obtain anilines with challenging substitution patterns. Additionally, a regioselective bromination system for para-bromination of aniline derivatives has been described, which operates under mild conditions and exhibits unique regioselectivity.

Molecular Structure Analysis

Vibrational analysis of similar molecules, such as 4-bromo-3-(trifluoromethyl)aniline, has been conducted using Fourier Transform-Infrared and Fourier Transform-Raman techniques, complemented by theoretical density functional theory computations. These studies provide insights into the effects of substituents on the vibrational spectra and molecular structure. Furthermore, the crystal structure of a related compound, 4-bromo-N-[4-(dimethylamino)benzylidene]aniline, has been characterized by X-ray diffraction, revealing the dihedral angles between aromatic rings and providing a deeper understanding of the structural characteristics of brominated aniline derivatives.

Chemical Reactions Analysis

The reactivity of 3-Bromo-5-(trifluoromethyl)aniline and its derivatives in various chemical reactions has been a subject of interest. For example, the para-bromination of aromatic amines has been studied, highlighting the use of bromination agents and the formation of products such as 4-bromo-N,N-dimethyl-3-(trifluoromethyl)aniline. These studies contribute to the understanding of halogenation reactions and the synthesis of brominated aromatic compounds.

Physical and Chemical Properties Analysis

The physical and chemical properties of 3-Bromo-5-(trifluoromethyl)aniline are influenced by the presence of the bromine and trifluoromethyl groups. A study involving the identification of unknown pharmaceutical impurities in this compound utilized liquid chromatography and nuclear magnetic resonance (NMR) techniques, which not only helped in impurity profiling but also shed light on the compound's behavior during chromatographic separation. Additionally, the vibrational, structural, thermodynamic, and electronic properties of related trifluoromethyl anilines have been extensively studied, providing valuable information on the influence of substituents on these properties.

Scientific Research Applications

• Pharmaceutical Research

  • Application : 3-Bromo-5-(trifluoromethyl)aniline is used as an intermediate in the synthesis of new anticancer drugs.
  • Method : The compound is synthesized from 4-bromo-2-trifluro toluidine through a series of reactions including acetylation, nitration, deacetylation, deamination, and reduction.
  • Results : The overall yield of the process is 43%, and the process is also suitable for the synthesis of 3-chloro-5-(trifluoromethyl)aniline and 3-fluoro-5-(trifluoromethyl)aniline.

• Biochemical Research

  • Application : 3-Bromo-5-(trifluoromethyl)aniline is used in the synthesis and biochemical evaluation of inhibitors of the hepatitis C virus (HCV) NS3 protease.

• Chemical Analysis

  • Application : 3-Bromo-5-(trifluoromethyl)aniline is used in the identification and structural characterization of unknown impurities.
  • Method : Liquid chromatography (LC) – solid-phase extraction (SPE) / nuclear magnetic resonance (NMR) methodology with cryoprobe is used for the identification and structural characterization.
  • Results : The structures of the unknown impurities were determined by detailed inspection of NMR spectra and by mass spectrometric (MS) analysis.

• Synthesis of New Compounds

  • Application : 3-Bromo-5-(trifluoromethyl)aniline has been used in the preparation of 2,5-dibromo-(trifluoromethyl)benzene and 2-bromo-5-iodo-(trifluoromethyl)benzene.

• Preparation of Schiff’s Base

  • Application : 3,5-Bis (trifluoromethyl)aniline was used in the synthesis of N - [2-hydroxy-1-naphthylidene]-3, 5- bis (trifluoromethyl)aniline, Schiff′s base.

• Titanium-Catalyzed Hydroamination Reaction

  • Application : 3,5-Bis (trifluoromethyl)aniline was used in the synthesis of 5,7- bis (trifluoromethyl)aniline N -1-phenylethyl-3,5- bis (trifluoromethyl)aniline via titanium-catalyzed hydroamination reaction.

• Preparation of 2,5-Dibromo-(trifluoromethyl)benzene and 2-Bromo-5-Iodo-(trifluoromethyl)benzene

  • Application : 4-Bromo-3-(trifluoromethyl)aniline has been used in the preparation of 2,5-dibromo-(trifluoromethyl)benzene and 2-bromo-5-iodo-(trifluoromethyl)benzene.

• Synthesis of Schiff’s Base

  • Application : 3,5-Bis (trifluoromethyl)aniline was used in the synthesis of N - [2-hydroxy-1-naphthylidene]-3, 5- bis (trifluoromethyl)aniline, Schiff′s base.

• Titanium-Catalyzed Hydroamination Reaction

  • Application : 3,5-Bis (trifluoromethyl)aniline was used in the synthesis of 5,7- bis (trifluoromethyl)aniline N -1-phenylethyl-3,5- bis (trifluoromethyl)aniline via titanium-catalyzed hydroamination reaction.

Safety And Hazards

The safety data sheet for 3-Bromo-5-(trifluoromethyl)aniline suggests that it may cause skin and eye irritation. It is recommended to avoid ingestion and inhalation, and to use personal protective equipment when handling this compound.

Future Directions

3-Bromo-5-(trifluoromethyl)aniline is an important intermediate in the synthesis of various pharmaceutical compounds, including novel anticancer drugs. The process for its synthesis is suitable for industrial-scale production. Future research may focus on improving the yield of the synthesis process and exploring new applications for this compound in pharmaceutical research.

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