203302-95-8 | 4-Bromo-3,5-difluoroaniline

CAS:203302-95-8 | 4-Bromo-3,5-difluoroaniline,Description

4-Bromo-3,5-difluoroaniline is a compound that is part of a broader class of bromoanilines, which are aromatic compounds containing a bromine atom attached to an aniline moiety. These compounds are often used as intermediates in the synthesis of more complex molecules, including pharmaceuticals and dyes. The presence of bromine and fluorine atoms in these compounds can significantly influence their reactivity and physical properties, making them valuable in various chemical transformations.

Synthesis Analysis

The synthesis of bromoaniline derivatives can be achieved through several methods. For instance, a synthesis method for a related compound, 4-chloro-2,5-difluorobenzoic acid, involves a Sandmeyer reaction, followed by bromination and a Grignard reaction, with the bromination step optimized for temperature and time to achieve a high purity product. Similarly, 4-bromo-3-methylanisole, another related compound, can be synthesized using a continuous homogeneous bromination technology in a modular microreaction system, which offers advantages over traditional batch processes in terms of selectivity and reaction conditions. These methods highlight the importance of optimizing reaction conditions to achieve high yields and purity in the synthesis of brominated aromatic compounds.

Molecular Structure Analysis

The molecular structure of bromoaniline derivatives can be elucidated using various analytical techniques. X-ray crystallography has been used to determine the crystal structures of dihydrogen hexafluorosilicate monohydrates of p-bromoaniline, revealing that these compounds form orthorhombic crystals with specific unit cell parameters and are cross-linked by ionic forces and hydrogen bonds. Additionally, the crystal structure of 5-(4-bromophenylamino)-2-methylsulfanylmethyl-2H-1,2,3-triazol-4-carboxylic acid ethyl ester, synthesized from p-bromoaniline, was investigated using X-ray crystallography, NMR, MS, and IR techniques, providing detailed information about the arrangement of atoms and the presence of hydrogen bonding.

Chemical Reactions Analysis

Bromoaniline derivatives can undergo various chemical reactions, making them versatile intermediates. For example, regiospecific allylic bromination has been used to synthesize a series of brominated ketones, which are useful in heterocyclic synthesis. The preparation of 1,3-dibromo-1,1-difluoro-2-propanone, a synthon used for the first time in a reaction with aromatic amines and sodium thiocyanate, leads to thiazoles with a bromodifluoromethyl group at the C4 position, demonstrating the potential for further transformations such as Br/F exchange. Additionally, a photocatalytic reaction involving N-aryl amino acids and 2-bromo-3,3,3-trifluoropropene has been used to synthesize 4-(difluoromethylidene)-tetrahydroquinolines, showcasing the utility of bromoaniline derivatives in photoredox chemistry.

Physical and Chemical Properties Analysis

The physical and chemical properties of bromoaniline derivatives are influenced by the presence of bromine and fluorine atoms. These substituents can affect the compound's boiling point, melting point, solubility, and stability. The introduction of these halogens can also impact the compound's electronic properties, such as electron-withdrawing or -donating effects, which in turn can influence the reactivity of the compound in various chemical reactions. The specific properties of 4-bromo-3,5-difluoroaniline would be expected to reflect these general trends, although the exact values would need to be determined experimentally.

Scientific Research Applications

• Synthesis of N-[(4-Bromo-3,5-Difluorine)Phenyl]acrylamide 
  • Application : This compound was synthesized for the first time by the interaction of 4-Bromo-3,5-difluoroaniline with acryloyl chloride.
  • Method : The synthesis involved the reaction of 4-Bromo-3,5-difluoroaniline with acryloyl chloride in the presence of triethylamine.
  • Results : The paper did not provide specific results or outcomes for this synthesis.
• Synthesis of Fluorinated Building Blocks 
  • Application : 4-Bromo-3,5-difluoroaniline is used in the synthesis of fluorinated building blocks.
  • Method : The specific methods and procedures can vary greatly depending on the particular synthesis or research study.
  • Results : The results or outcomes can also vary greatly depending on the specific synthesis or research study.
• Preparation of 3,5-Difluorodimethylaniline 
  • Application : 3,5-Difluoroaniline, a related compound to 4-Bromo-3,5-difluoroaniline, has been used in the preparation of 3,5-difluorodimethylaniline.
  • Method : The specific methods and procedures can vary greatly depending on the particular synthesis or research study.
  • Results : The results or outcomes can also vary greatly depending on the specific synthesis or research study.
• Synthesis of Fluorinated Compounds 
  • Application : 4-Bromo-3,5-difluoroaniline is used in the synthesis of various fluorinated compounds.
  • Method : The specific methods and procedures can vary greatly depending on the particular synthesis or research study.
  • Results : The results or outcomes can also vary greatly depending on the specific synthesis or research study.
• Preparation of 3,5-Difluorodimethylaniline 
  • Application : 3,5-Difluoroaniline, a related compound to 4-Bromo-3,5-difluoroaniline, has been used in the preparation of 3,5-difluorodimethylaniline.
  • Method : The specific methods and procedures can vary greatly depending on the particular synthesis or research study.
  • Results : The results or outcomes can also vary greatly depending on the specific synthesis or research study.
• General Organic Synthesis 
  • Application : 4-Bromo-3,5-difluoroaniline is a useful reactant in general organic synthesis.
  • Method : The specific methods and procedures can vary greatly depending on the particular synthesis or research study.
  • Results : The results or outcomes can also vary greatly depending on the specific synthesis or research study.

Safety And Hazards

4-Bromo-3,5-difluoroaniline is harmful if swallowed, in contact with skin, or if inhaled. It causes skin irritation and serious eye irritation. Safety measures include avoiding dust formation, breathing mist, gas or vapours, and contacting with skin and eye. Use of personal protective equipment and ensuring adequate ventilation are recommended.

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