928783-85-1 | 3-Bromo-5-Chlorobenzotrifluoride

CAS:928783-85-1 | 3-Bromo-5-Chlorobenzotrifluoride,Description

The compound 1-Bromo-3-chloro-5-(trifluoromethyl)benzene is a halogenated aromatic molecule that contains bromine, chlorine, and a trifluoromethyl group attached to a benzene ring. This structure suggests potential reactivity in organometallic chemistry and could serve as a versatile starting material for various chemical transformations due to the presence of reactive halogen atoms which can be substituted through different reactions.

Synthesis Analysis

The synthesis of halogenated benzene derivatives often involves selective halogenation reactions. For instance, 1-Bromo-3,5-bis(trifluoromethyl)benzene, a related compound, can be prepared by treating 1,3-bis(fluoromethyl)benzene with N,N'-dibromo-5,5-dimethylhydantoin in acidic media. Although the specific synthesis of 1-Bromo-3-chloro-5-(trifluoromethyl)benzene is not detailed in the provided papers, similar methodologies could be applied, adjusting the halogenation agents and conditions to introduce the chlorine and bromine atoms at the desired positions on the benzene ring.

Molecular Structure Analysis

The molecular structure of halogenated benzenes can be influenced by the substituents attached to the benzene ring. For example, the presence of bulky groups can lead to the formation of rotational isomers, as seen in 1-bromo-2,3,5,6-tetrakis(3-pentyl)benzene. The trifluoromethyl group in 1-Bromo-3-chloro-5-(trifluoromethyl)benzene is expected to have a significant electron-withdrawing effect, which could influence the reactivity and molecular conformation of the compound.

Chemical Reactions Analysis

Halogenated benzenes are known to undergo various chemical reactions, including cross-coupling reactions, as seen with ethynylferrocene compounds of 1,3,5-tribromobenzene. The bromine and chlorine atoms in 1-Bromo-3-chloro-5-(trifluoromethyl)benzene make it a potential candidate for further functionalization through reactions such as the Suzuki coupling or the formation of organometallic intermediates like phenylmagnesium, phenyllithium, or phenylcopper species.

Physical and Chemical Properties Analysis

The physical and chemical properties of halogenated benzenes can vary widely depending on the nature and position of the substituents. For example, the introduction of a trifluoromethyl group can increase the compound's lipophilicity and chemical stability. The presence of halogens can also lead to specific intermolecular interactions, such as hydrogen bonding and halogen bonding, which can influence the compound's crystal structure and solubility.

Scientific Research Applications

Application 1: Synthesis of Trifluoromethylpyridines

• Summary of the Application: Trifluoromethylpyridines (TFMP) and its derivatives are used in the agrochemical and pharmaceutical industries. The major use of TFMP derivatives is in the protection of crops from pests.
• Methods of Application: Various methods of synthesizing 2,3,5-DCTF have been reported. The synthesis involves chemical reactions with i-PrMgCl-LiCl in THF at 0°C.
• Results or Outcomes: More than 20 new TFMP-containing agrochemicals have acquired ISO common names. Several TFMP derivatives are also used in the pharmaceutical and veterinary industries.

Application 2: FDA-Approved Trifluoromethyl Group-Containing Drugs

• Summary of the Application: Trifluoromethyl (TFM, -CF3)-group-containing drugs have been approved by the FDA over the last 20 years.
• Methods of Application: The review covers the detailed chemistry of 19 FDA-approved drugs in the past 20 years, which contains the TFM group as one of the pharmacophores.
• Results or Outcomes: These drugs have been found to exhibit numerous pharmacological activities.

Application 3: Synthesis of Electrophilic Organic and Organometallic Cations

• Summary of the Application: 1,3-Bis (trifluoromethyl)-5-bromobenzene is used to prepare the tetrakis [3,5-bis (trifluoromethyl)phenyl]borate ion, which acts as a stabilizing counterion for electrophilic organic and organometallic cations.
• Methods of Application: The synthesis involves chemical reactions.
• Results or Outcomes: The tetrakis [3,5-bis (trifluoromethyl)phenyl]borate ion has been successfully synthesized.

Application 4: Synthesis of 2,4,6-Tris(trifluoromethyl)benzoic Acid

• Summary of the Application: 1,3,5-tris(trifluoromethyl)benzene is used as a starting material in the synthesis of 2,4,6-tris(trifluoromethyl)benzoic acid.
• Methods of Application: The synthesis involves reacting with n-butyllithium and carbon dioxide.
• Results or Outcomes: 2,4,6-Tris(trifluoromethyl)benzoic acid has been successfully synthesized.

Application 5: Preparation of Tetrakis[3,5-bis(trifluoromethyl)phenyl]borate Ion

• Summary of the Application: 1,3-Bis(trifluoromethyl)-5-bromobenzene is used to prepare the tetrakis[3,5-bis(trifluoromethyl)phenyl]borate ion.
• Methods of Application: The preparation involves chemical reactions.
• Results or Outcomes: The tetrakis[3,5-bis(trifluoromethyl)phenyl]borate ion has been successfully prepared.

Application 6: Synthesis of Fluorinated Organic Chemicals

• Summary of the Application: 1,3,5-tris(trifluoromethyl)benzene is used as a starting material in the synthesis of fluorinated organic chemicals. These compounds have found numerous applications in the agrochemical, pharmaceutical, and functional materials fields.
• Methods of Application: The synthesis involves various chemical reactions.
• Results or Outcomes: More than 50% of the pesticides launched in the last two decades have been fluorinated. Around 40% of all fluorine-containing pesticides currently on the market contain a trifluoromethyl group.

Safety And Hazards

This compound is labeled with the GHS07 pictogram and has the signal word "Warning". Hazard statements include H302, H315, H319, and H335, indicating that it is harmful if swallowed, causes skin and eye irritation, and may cause respiratory irritation. Precautionary measures include avoiding breathing dust/fume/gas/mist/vapours/spray and wearing protective gloves/clothing/eye protection/face protection.

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