443-86-7 | 3-Fluoro-2-methylaniline

CAS:443-86-7 | 3-Fluoro-2-methylaniline,Description

3-Fluoro-2-methylaniline is a fluorinated aniline derivative, which is a type of aromatic amine featuring both a methyl and a fluorine substituent on the benzene ring. The presence of these substituents can significantly alter the chemical and physical properties of the compound compared to aniline itself.

Synthesis Analysis

The synthesis of fluorinated aniline derivatives, such as 3-fluoro-2-methylaniline, can be achieved through various chemical routes. One approach involves the use of a nucleoside that is modified to include a 3-fluoro-6-methylaniline group, which can then be incorporated into oligonucleotides for further applications. Another method for synthesizing polyfluoroanilines, which could potentially be adapted for 3-fluoro-2-methylaniline, involves acid-assisted persulfate initiated polymerization of fluorine-substituted aniline monomers.

Molecular Structure Analysis

The molecular structure of related compounds, such as 2,6-dibromo-3-chloro-4-fluoroaniline, has been determined through crystallographic methods. These compounds crystallize in the monoclinic system and feature classical intra- and intermolecular hydrogen bonds, as well as dispersive halogen interactions. Although not directly about 3-fluoro-2-methylaniline, this study provides insight into how halogen substituents can influence the molecular structure and interactions within the crystal lattice.

Chemical Reactions Analysis

The chemical reactivity of fluorinated anilines can be quite distinct due to the electron-withdrawing nature of the fluorine atom. For instance, the 3-fluoro group in a nucleoside derivative has been utilized as a spin label in 19F NMR studies, which can provide detailed information on mercury-mediated base pairing in nucleic acids. Additionally, the activated fluorine-amine reaction has been used to synthesize guanidinium-functionalized polymer electrolytes, demonstrating the versatility of fluorinated anilines in polymer chemistry.

Physical and Chemical Properties Analysis

The physical and chemical properties of 3-fluoro-2-methylaniline derivatives can be characterized using various spectroscopic and analytical techniques. UV-VIS, FT-IR, and NMR spectroscopies are commonly employed to characterize the structure and purity of these compounds. Additionally, differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) can provide information on the thermal stability and decomposition patterns of polyfluoroaniline polymers. The solubility of these compounds in organic solvents can also be an important physical property, influencing their applications in different chemical processes.

Scientific Research Applications

1. Nucleobase-Specific Hybridization Probe

A study by Aro-Heinilä, Lönnberg, and Virta (2019) explored the use of a 3-fluoro-6-methylaniline nucleoside in oligonucleotides, demonstrating its effectiveness as a mercury-mediated base pairs stabilizer. This compound showed a clear nucleobase-specific binding preference and was utilized as a spin label for detailed analysis of Hg(II)-mediated base pairing using 19F NMR resonance shifts (Aro-Heinilä, Lönnberg, & Virta, 2019) .

2. Environmental Toxicology

In environmental toxicology, Bundy et al. (2002) investigated the effects of 2-fluoro-4-methylaniline on earthworms. Using high-resolution 1H NMR spectroscopy, they assessed toxicant-induced biochemical changes in earthworm tissue extracts. This study identified new endogenous biomarkers of xenobiotic toxicity, contributing to understanding the mechanism of action of toxic chemicals (Bundy et al., 2002) .

3. Crystallography

In the field of crystallography, Mayes, McGarry, Moussa, and Watkin (2008) reported on the chlorination of 3-fluoro-2-methylaniline, analyzing the crystal structure of the resultant compound. They found that the crystal structure was stabilized by hydrogen-bonding and π–π stacking interactions (Mayes, McGarry, Moussa, & Watkin, 2008) .

4. Vibrational Spectroscopy

Lijuan Zhang et al. (2014) conducted REMPI spectroscopy and theoretical calculations on 3-fluoro-N-methylaniline (3FNMA), studying its vibrational spectra in different states. This research provided insights into the conformation effects and the stability of different rotamers in 3FNMA (Lijuan Zhang et al., 2014).

Safety And Hazards

3-Fluoro-2-methylaniline is harmful if swallowed, in contact with skin, or if inhaled. It causes skin irritation and serious eye irritation. It is also a combustible liquid.

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