2iodobenzoic

2-iodobenzoic acid, also known as o-iodobenzoic acid, is an organoiodine compound that represents the ortho-iodinated derivative of benzoic acid. Its chemical formula is C7H5IO2, reflecting the substitution of one hydrogen on the benzene ring by iodine adjacent to the carboxyl group.

In the molecule, the iodine substituent sits at the 2-position relative to the carboxyl group on the aromatic ring, giving the ortho isomer. This arrangement makes 2-iodobenzoic acid a versatile aryl iodide for synthetic chemistry and a common building block in organic synthesis.

Preparation of 2-iodobenzoic acid is typically achieved by electrophilic iodination of benzoic acid or related substrates, with regioselectivity influenced by reaction conditions. Alternative routes include transformations from salicylic acid derivatives or from preformed 2-halo benzoic acid precursors.

Reactions and applications: as an aryl iodide, 2-iodobenzoic acid participates readily in palladium- or copper-catalyzed cross-coupling reactions such as Suzuki–Miyaura and Sonogashira couplings, enabling the construction of substituted biaryl or alkynyl benzoic acid derivatives. The carboxyl group can function as a handle for further transformations or protection strategies, and the C–I bond generally offers higher reactivity in cross-coupling than corresponding C–Cl bonds.

Properties and safety: it is typically a crystalline solid with limited water solubility and higher solubility in organic solvents. Like many organoiodine compounds, it can be an irritant and should be handled with appropriate personal protective equipment in a well-ventilated area, away from incompatible materials.