769-10-8 | 2-Fluoro-6-nitrotoluene

CAS:769-10-8 | 2-Fluoro-6-nitrotoluene,Description

2-Fluoro-6-nitrotoluene (FNT) is a chemical compound that has been the subject of various studies due to its importance as an intermediate in medical and organic synthesis applications. The compound is characterized by the presence of a fluorine atom and a nitro group attached to a toluene ring, which significantly alters its chemical and physical properties compared to toluene itself.

Synthesis Analysis

The synthesis of related fluorinated aromatic compounds has been explored in the literature. A highly efficient method for the synthesis of 2-fluoro-2-nitrostyrenes, which are structurally similar to FNT, involves the radical nitration of 2-bromo-2-fluorostyrenes with iron(III) nitrate nonahydrate. This process yields the corresponding α-fluoro-nitroalkenes with high selectivity and in isolated yields up to 92%. Additionally, 2-Bromo-6-fluorotoluene, a compound closely related to FNT, has been synthesized from 2-Amino-6-nitrotoluene through a series of reactions including Gattermann diazonium salt substitution, reduction, and Schiemann reaction, with a yield of 51.8%.

Molecular Structure Analysis

The molecular structure and conformational behavior of FNT have been investigated using density functional theory (DFT) calculations. The vibrational wavenumbers were computed at DFT levels, and complete vibrational assignments were made based on normal coordinate calculations. The results of these analyses were compared with experimental values from Fourier transform infrared (FTIR) and Fourier transform (FT) Raman vibrational wavenumbers, providing insights into the structural stability of FNT.

Chemical Reactions Analysis

While specific chemical reactions of FNT are not detailed in the provided papers, the studies of related fluorinated aromatic compounds suggest that FNT could potentially undergo similar reactions due to the presence of reactive functional groups. The fluorine atom and nitro group on the aromatic ring can influence the reactivity and selectivity of subsequent chemical transformations.

Physical and Chemical Properties Analysis

The physical and chemical properties of FNT can be inferred from vibrational spectroscopy studies. The vibrational spectra of FNT and its comparison with other toluene derivatives provide information about the influence of substituents on the toluene ring. The vibrational analysis, supported by normal coordinate analysis (NCA), helps in understanding the stability and reactivity of the molecule. The assignments of bands to various normal modes of the molecules were also carried out, contributing to a deeper understanding of the compound's properties.

Scientific Research Applications

• Summary of the Application : 2-Fluoro-6-nitrotoluene is used as a starting material in the synthesis of 4-fluoroindole. Indoles are a class of organic compounds that are widely used in medicinal chemistry and drug discovery due to their biological activity.
• Methods of Application or Experimental Procedures : The specific experimental procedure is known as the Leimgruber-Batcho procedure. While the exact details of the procedure were not found, the Leimgruber-Batcho procedure typically involves the conversion of an arylamine to an indole through a series of reactions including diazotization, coupling, and cyclization.
• Results or Outcomes : The outcome of this procedure is the production of 4-fluoroindole. The yield, purity, and other quantitative data were not specified in the sources found.

Safety And Hazards

2-Fluoro-6-nitrotoluene is classified as a combustible liquid. It is harmful if swallowed, in contact with skin, or if inhaled. It causes skin irritation and serious eye irritation. It may also cause respiratory irritation. It is advised to avoid breathing dust/fume/gas/mist/vapors/spray, and to use only outdoors or in a well-ventilated area.

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