4-Nitrobenzoyl chloride

Air & Water Reactions

Unstable in moist surroundings and should be kept in a tightly-closed container. React with water or steam .

Reactivity Profile

4-Nitrobenzoyl chloride is incompatible with bases (including amines), with strong oxidizing agents, and with alcohols. May react with reducing agents. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Flash point data are not available for 4-Nitrobenzoyl chloride, but 4-Nitrobenzoyl chloride is combustible.

Safety Profile

Moderately toxic by ingestion. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx and Cl-. See also NITRO COhlPOUNDS OF AROMATIC HYDROCARBONS and CHLORIDES.

Purification Methods

Crystallise the acid chloride from dry pet ether (b 60-80o), *C6H6 or CCl4. Distil it under vacuum. Irritant. [Adama & Jenkins Org Synth Coll Vol I 394 1941, Beilstein 9 III 1709, 9 IV 1191.]

General Description

4-Nitrobenzoyl chloride, also known as p-nitrobenzoyl chloride or 4-nitrobenzoic acid chloride, is a reactive acylating agent used in organic synthesis. It serves as a key intermediate in the preparation of various compounds, including amides, esters, and acetylenes, as demonstrated in studies involving the acylation of amines and phenols, the synthesis of arylacetylenes, and the development of colorimetric anion sensors. Its reactivity makes it valuable in green chemistry applications, such as hydrotalcite-catalyzed reactions in water, and in the design of functional materials like anion-sensing dyes. 4-Nitrobenzoyl chloride's nitro group enhances its electrophilicity, facilitating nucleophilic substitution reactions.