ochlorobenzaldehyde

o-Chlorobenzaldehyde, also called 2-chlorobenzaldehyde, is an aromatic aldehyde in which a chlorine atom is attached to the ortho position relative to the formyl group. Its chemical formula is C7H5ClO. It is typically used as a chemical intermediate in organic synthesis and can be found commercially.

Production and related chemistry

o-Chlorobenzaldehyde is usually prepared by chlorination of benzaldehyde under suitable catalytic conditions, with purification used to isolate the ortho isomer from other chlorinated benzaldehydes. It can also be prepared via alternative routes that introduce the chlorine substituent onto a benzaldehyde framework. The compound serves as a versatile building block for further transformations, including nucleophilic substitutions and condensation reactions.

Properties and behavior

The compound is generally a colorless to pale yellow solid or liquid at room temperature, with the characteristic odor associated with benzaldehydes. The aldehyde group participates in standard reactions, such as oxidation to the corresponding chlorobenzaldehyde-derived carboxylic acids, reduction to the corresponding benzyl alcohol, and various electrophilic or nucleophilic aromatic substitutions at other positions on the ring. The presence of the ortho chlorine can influence reactivity and directing effects in subsequent substitutions.

Applications

o-Chlorobenzaldehyde is used as an intermediate in the synthesis of dyes, pharmaceuticals, agrochemicals, and fragrances. It serves as a convenient starting point for preparing more complex heterocycles and substituted benzaldehydes, including derivatives used in medicinal chemistry and material science.

Safety and handling

The compound is typically handled under standard laboratory safety practices for irritant and potentially toxic organic halides. It may pose inhalation or skin contact risks and should be stored away from heat and incompatible substances. Proper disposal and ventilation are recommended.