2Fluoroaniline

2-Fluoroaniline, also known as o-fluoroaniline, is an aromatic amine in which a fluorine atom occupies the ortho position relative to the amino group on a benzene ring. Its molecular formula is C6H6FN and its molecular weight is about 111.1 g/mol. The compound is typically a colorless to pale yellow liquid that is more soluble in organic solvents than in water.

Chemistry and properties: The amino group behaves as a modest base, and the fluorine substituent at the ortho position withdraws electron density via inductive effects. This can reduce basicity relative to unsubstituted aniline and influence the ring’s reactivity in electrophilic aromatic substitution and cross-coupling reactions. The ortho fluoro substituent also introduces steric effects that can affect binding and transformation in subsequent chemical steps.

Preparation and handling: 2-Fluoroaniline is commonly prepared by the selective reduction of 2-fluoronitrobenzene. It can also be accessed via diazotization of the corresponding aniline followed by substitution routes. It is typically handled under appropriate safety protocols in a fume hood, with personal protective equipment, as it is toxic and can irritate skin, eyes, and the respiratory tract.

Applications: This compound serves as an intermediate in the synthesis of fluorinated pharmaceuticals, dyes, and agrochemicals. The fluorine atom can impart metabolic and electronic properties that are valuable in downstream functionalization, including diazotization to diazonium salts for Sandmeyer-type transformations and various palladium-catalyzed cross-coupling reactions.