38573-88-5 | 1-Bromo-2,3-difluorobenzene

CAS:38573-88-5 | 1-Bromo-2,3-difluorobenzene,Description

1-Bromo-2,3-difluorobenzene is an aromatic compound that is part of the bromofluorobenzene family, where bromine and fluorine atoms are substituted onto a benzene ring. The presence of these halogens significantly alters the chemical and physical properties of the benzene ring, making it a compound of interest in various chemical syntheses and studies.

Synthesis Analysis

The synthesis of halogenated benzene derivatives, including 1-bromo-2,3-difluorobenzene, often involves halogenation reactions where bromine and fluorine are introduced into the benzene ring. For instance, the CuI-catalyzed domino process described in one study allows for the coupling of 1-bromo-2-iodobenzenes with beta-keto esters to form benzofurans, showcasing the reactivity of brominated benzene compounds in creating more complex structures. Additionally, the synthesis of sterically hindered phosphine derivatives from tetrafluorobenzene indicates the versatility of halogenated benzenes as precursors in organometallic chemistry.

Molecular Structure Analysis

The molecular structure of halogenated benzenes, including those with bromine and fluorine substituents, has been studied using various methods such as electron diffraction and X-ray crystallography. These studies have revealed bond distances and angles that deviate from normal single bond characters due to the presence of halogens, which can introduce partial double bond character. The molecular symmetry of these compounds plays a crucial role in their reactivity and interactions, as seen in photodissociation studies.

Chemical Reactions Analysis

1-Bromo-2,3-difluorobenzene can undergo various chemical reactions due to the presence of reactive halogen atoms. Photodissociation dynamics of bromofluorobenzenes have been explored, revealing complex mechanisms involving multiple internal molecular coordinates. Organometallic methods have been used to control the regiospecificity of functionalization reactions, demonstrating the ability to selectively introduce additional substituents onto the benzene ring. These reactions are essential for creating a wide range of derivatives for further applications.

Physical and Chemical Properties Analysis

The physical and chemical properties of 1-bromo-2,3-difluorobenzene are influenced by the halogen substituents. Spectroscopic methods such as FT-IR and FT-Raman, along with UV spectroscopy and DFT calculations, have been employed to investigate these properties. These studies provide insights into the vibrational frequencies, electronic properties, and molecular orbital energies, which are important for understanding the reactivity and stability of the compound. The crystal structure and molecular conformation of related brominated compounds have also been characterized, offering information on the solid-state properties and phase behavior.

Scientific Research Applications

Synthesis of Potent CGRP Receptor Antagonist

• Application Summary : 1-Bromo-2,3-difluorobenzene is used in the synthesis of a potent, orally active Calcitonin gene-related peptide (CGRP) receptor antagonist (BMS-846372).

Preparation of 2,3-Difluorophenyl (Dimethyl)Phosphane

• Application Summary : 1-Bromo-2,3-difluorobenzene is used in the preparation of 2,3-difluorophenyl (dimethyl)phosphane.

Synthesis of Antiviral Drugs

• Application Summary : 1-Bromo-2,3-difluorobenzene is used as a key intermediate in the synthesis of various pharmaceuticals, including antiviral drugs.
• Results or Outcomes : For example, it is used in the synthesis of Oseltamivir (Tamiflu) , which is a widely used antiviral drug for the treatment of influenza.

Synthesis of Agrochemicals

• Application Summary : 1-Bromo-2,3-difluorobenzene is also used in the synthesis of various agrochemicals, including herbicides, insecticides, and fungicides.
• Results or Outcomes : For example, it is used in the synthesis of Flumioxazin , which is a herbicide used to control weeds in crops like soybeans, peanuts, and cotton.

Synthesis of Materials

• Application Summary : 1-Bromo-2,3-difluorobenzene is also used in the synthesis of various materials, including liquid crystals, polymers, and OLEDs.
• Results or Outcomes : For example, it is used in the synthesis of a liquid crystal material called 4- (4-dodecylphenyl)-4’-cyanobiphenyl (DDCB) , which has excellent thermal stability and electro-optic properties.

Microbial Oxidation

• Application Summary : 1-Bromo-2,3-difluorobenzene has been reported to undergo microbial oxidation by Pseudomonas putida strain 39/D and Escherichia coli recombinant microorganism (strain JM 109 (pDTG601)).
• Results or Outcomes : The outcome of this application is the microbial oxidation of 1-Bromo-2,3-difluorobenzene.

Synthesis of Anti-Inflammatory Agents

• Application Summary : 1-Bromo-2,3-difluorobenzene is used as a key intermediate in the synthesis of various pharmaceuticals, including anti-inflammatory agents.
• Results or Outcomes : The outcome of this application is the synthesis of various anti-inflammatory agents.

Synthesis of Cancer Therapeutics

• Application Summary : 1-Bromo-2,3-difluorobenzene is used as a key intermediate in the synthesis of various pharmaceuticals, including cancer therapeutics.
• Results or Outcomes : The outcome of this application is the synthesis of various cancer therapeutics.

Safety And Hazards

1-Bromo-2,3-difluorobenzene is considered hazardous. It is a combustible liquid that causes skin irritation and serious eye irritation. It may also cause respiratory irritation. In case of fire, CO2, dry chemical, or foam should be used for extinction. It should be stored in a well-ventilated place, with the container kept tightly closed and locked up.

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