Benzoyl chloride

Benzoyl chloride is the aromatic acyl chloride C₆H₅COCl. It transfers benzoyl groups to nucleophiles and reacts readily with water, alcohols, and amines.

Nucleophilic acyl substitution: A reaction in which a nucleophile replaces a substituent attached to an acyl carbon. Nucleophiles replace chloride at its carbonyl carbon to form benzoylated products.
Benzoyl protecting group: A benzoyl group temporarily attached to a functional group to control its reactivity during synthesis. Benzoyl chloride installs this protecting group on alcohols and amines.
Acyl chloride: A carboxylic acid derivative in which the hydroxyl group is replaced by chlorine. Benzoyl chloride is the aromatic member of this reactive compound family.
Acetyl chloride: The acyl chloride CH₃COCl, which transfers acetyl groups in organic synthesis. It is a smaller aliphatic counterpart without benzoyl chloride’s aromatic ring.
Benzoylation: The introduction of a benzoyl group into a molecule. This is the characteristic transformation performed with benzoyl chloride.
Schotten–Baumann reaction: A biphasic acylation method that reacts an acyl chloride with a nucleophile in aqueous base. This classical procedure uses benzoyl chloride to benzoylate amines or alcohols.
Benzoyl group: The acyl substituent C₆H₅CO–, derived formally from benzoic acid. The reagent’s main synthetic role is transferring this fragment to other molecules.
Benzoyl bromide: The aromatic acyl halide C₆H₅COBr, containing bromine instead of chlorine. Its different halide leaving group provides a direct structural comparison.
Benzamide: The amide C₆H₅CONH₂, formed by replacing benzoyl chloride’s chlorine with an amino group. Ammonia reacts with benzoyl chloride to produce this primary amide.
Hippuric acid: The glycine conjugate of benzoic acid, excreted in urine by humans and other animals. Benzoyl chloride can benzoylate glycine in preparations of this compound.

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