454-73-9 | 3-FLUORO-5-NITROBENZOTRIFLUORIDE

CAS:454-73-9 | 3-FLUORO-5-NITROBENZOTRIFLUORIDE,Description

Synthesis Analysis

The synthesis of related fluoro-nitro-trifluoromethyl benzene compounds involves various methods, including direct fluorination and nucleophilic aromatic substitution reactions. One study outlines the preparation of 3-fluoro-5-nitro-1-(pentafluorosulfanyl)benzene through direct fluorination and fluorodenitration processes, showcasing the versatility in synthesizing fluorinated benzene derivatives with complex substituents (Beilstein Journal of Organic Chemistry, 2016).

Molecular Structure Analysis

The molecular structure of fluoro-nitro-trifluoromethyl benzene derivatives is characterized by the presence of fluorine and nitro groups attached to a benzene ring, significantly influencing their electronic properties. The spatial arrangement of these substituents affects the compound's reactivity and interactions with nucleophiles, as seen in studies involving nucleophilic aromatic substitution (Journal of Fluorine Chemistry, 2003).

Chemical Reactions and Properties

Fluoro-nitro-trifluoromethyl benzene compounds participate in a variety of chemical reactions, including nucleophilic aromatic substitution, where the fluorine atom can be replaced by other nucleophiles. This reactivity pattern opens pathways for synthesizing a wide range of derivatives with different functional groups positioned strategically on the benzene ring (Synthesis, 2002).

Physical Properties Analysis

The physical properties of 1-fluoro-3-nitro-5-(trifluoromethyl)benzene derivatives, such as solubility, melting point, and boiling point, are significantly influenced by the presence of the fluorine and nitro groups. These groups enhance the compound's polarity, affecting its behavior in different solvents and under various temperature conditions.

Chemical Properties Analysis

Chemically, the trifluoromethyl and nitro groups impart a high degree of reactivity to the benzene ring, facilitating electrophilic and nucleophilic reactions. The electron-withdrawing nature of these groups also affects the acid-base properties of the compound, making it an interesting subject for studies involving its reactivity towards different chemical reagents (Journal of Organic Chemistry, 2022).

Scientific Research Applications

1. Agrochemical and Pharmaceutical Industries

• 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 : The synthesis and applications of TFMP and its derivatives involve various chemical reactions. For instance, 2,3-dichloro-5-(trifluoromethyl)-pyridine (2,3,5-DCTF), which is used as a chemical intermediate for the synthesis of several crop-protection products, is in high demand.
• Results : More than 20 new TFMP-containing agrochemicals have acquired ISO common names. Several TFMP derivatives are also used in the pharmaceutical and veterinary industries; five pharmaceutical and two veterinary products containing the TFMP moiety have been granted market approval.

2. FDA-Approved Drugs

• Application : Trifluoromethyl (TFM, -CF3)-group-containing drugs have been approved by the FDA over the last 20 years.
• Methods : The synthesis of these drugs involves various chemical reactions, including the incorporation of the CF3 group into potential drug molecules.
• Results : 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.

3. Synthesis of Organic Compounds

• Application : 1,3,5-tris(trifluoromethyl)benzene may be used as a starting material in the synthesis of 2,4,6-tris (trifluoromethyl)benzoic acid.
• Methods : The synthesis involves reacting with n-butyl lithium and carbon dioxide.
• Results : The result is the synthesis of 2,4,6-tris (trifluoromethyl)benzoic acid.

Safety And Hazards

1-Fluoro-3-nitro-5-(trifluoromethyl)benzene is considered hazardous by the 2012 OSHA Hazard Communication Standard (29 CFR 1910.1200). It is classified as a flammable liquid, skin corrosive/irritant, serious eye damage/eye irritant, and specific target organ toxicant (single exposure) with the target organ being the respiratory system.

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