21397-08-0 | 2-Chloro-3-fluoroaniline

CAS:21397-08-0 | 2-Chloro-3-fluoroaniline,Description

2-Chloro-3-fluoroaniline is a compound that is part of a broader class of chemicals known as halogenated anilines. These compounds are characterized by the presence of halogen atoms (such as chlorine and fluorine) attached to an aniline structure, which is a benzene ring connected to an amino group (NH2). The specific arrangement of chlorine and fluorine atoms on the benzene ring can significantly influence the chemical and physical properties of these compounds, as well as their reactivity and potential applications in various chemical syntheses.

Synthesis Analysis

The synthesis of halogenated anilines, including compounds like 2-chloro-3-fluoroaniline, can be achieved through various methods. One approach involves the preparation of α-chloro-1,2-diones and α-fluoro-1,2-diones from corresponding α-chloroaldimines. This process includes a sequence of reactions such as cyanation to α-cyanoenamines, α-halogenation to form α-chloro- or α-fluoroimidoyl cyanides, and addition of organolithium reagents followed by acidic hydrolysis, leading to chlorinated and fluorinated 1,2-diones in good yields.

Molecular Structure Analysis

The molecular structure of halogenated anilines is crucial in determining their physical and chemical properties. For instance, the crystal and molecular structure of a related compound, 2,6-dibromo-3-chloro-4-fluoroaniline, has been determined to be monoclinic with specific lattice parameters. The presence of classical intra- and intermolecular hydrogen bonds, as well as dispersive halogen···halogen interactions, are observed in the crystal structure. These interactions can influence the stability and reactivity of the compound.

Chemical Reactions Analysis

Halogenated anilines undergo various chemical reactions based on their functional groups and substituents. For example, the synthesis of 2'-chloro-2',3'-dideoxy-3'-fluoro-d-ribonucleosides involves the use of a glycosylating agent for persilylated bases, followed by transformations to different nucleoside derivatives through reactions such as treatment with tributyltin hydride and elimination of HF. Additionally, the chemical polymerization of 2-chloroaniline and 2-fluoroaniline can be carried out using oxidants like chromic acid, with the oxidizing power enhanced by HCl, leading to the formation of polymers with specific characteristics.

Physical and Chemical Properties Analysis

The physical and chemical properties of 2-chloro-3-fluoroaniline are influenced by the halogen substituents on the aromatic ring. The presence of chlorine and fluorine can affect the electron distribution within the molecule, thereby impacting its reactivity. For instance, the conformational properties of 2-fluoroanisole, a related compound, have been studied, revealing the existence of planar and nonplanar forms and providing insights into the stereochemical peculiarities of ortho-substituted anisoles. Furthermore, the synthesis and reactions of 3-chloro-2-fluoro-2-buten-4-olide, a tetronic acid analogue, demonstrate the influence of halogen substituents on the reactivity towards hard and soft nucleophiles.

Scientific Research Applications

Crystal Structure Analysis

• Crystal and Molecular Structure : Research on structurally similar compounds, like 2,6-dibromo-3-chloro-4-fluoroaniline, reveals insights into the crystal and molecular structure of these compounds. Such studies help in understanding the intra- and intermolecular interactions, which are crucial for the development of materials with specific properties (Betz, 2015).

Spectroscopy and Material Analysis

• Spectroscopy Studies : The 3-Chloro-4-fluoroaniline and similar compounds have been studied using techniques like resonant two-photon ionization and mass-analyzed threshold ionization spectroscopy. These studies provide valuable data for molecular identification and understanding the interactions among various substituents (Kononov Lo & W. Tzeng, 2013).

Safety And Hazards

2-Chloro-3-fluoroaniline should be handled with care. Conditions to avoid include heat, flames, and sparks. Materials to avoid include oxidizing agents. Possible hazardous combustion products include carbon monoxide, nitrogen oxides, hydrogen chloride, and hydrogen fluoride. Safety data sheets provide more detailed safety information.

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