In organic chemistry, quaternary ammonium cations, also known as quats, are positively-charged polyatomic ions of the structure [NR₄]⁺, where R is an alkyl group, an aryl group or organyl group. Unlike the ammonium ion (NH+4) and the primary, secondary, or tertiary ammonium cations, the quaternary ammonium cations are permanently charged, independent of the pH of their solution. Quaternary ammonium salts or quaternary ammonium compounds (called quaternary amines in oilfield parlance) are salts of quaternary ammonium cations. Polyquats are a variety of engineered polymer forms which provide multiple quat molecules within a larger molecule.

Quats are used in consumer applications including as antimicrobials (such as detergents and disinfectants), fabric softeners, and hair conditioners. As an antimicrobial, they are able to inactivate enveloped viruses (such as SARS-CoV-2). Quats tend to be gentler on surfaces than bleach-based disinfectants, and are generally fabric-safe.

Quaternary ammonium compounds are prepared by the alkylation of tertiary amine. Industrial production of commodity quat salts usually involves hydrogenation of fatty nitriles, which can generate primary or secondary amines. These amines are then treated with methyl chloride.

The quaternization of alkyl amines by alkyl halides is widely documented. In older literature this is often called a Menshutkin reaction, however modern chemists usually refer to it simply as quaternization. The reaction can be used to produce a compound with unequal alkyl chain lengths; for example when making cationic surfactants one of the alkyl groups on the amine is typically longer than the others. A typical synthesis is for benzalkonium chloride from a long-chain alkyldimethylamine and benzyl chloride:

Quaternary ammonium cations are unreactive toward even strong electrophiles, oxidants, and acids. They also are stable toward most nucleophiles. The latter is indicated by the stability of the hydroxide salts such as tetramethylammonium hydroxide and tetrabutylammonium hydroxide even at elevated temperatures. The halflife of Me₄NOH in 6M NaOH at 160 °C is >61 h.

Because of their resilience, many unusual anions have been isolated as the quaternary ammonium salts. Examples include tetramethylammonium pentafluoroxenate, containing the highly reactive pentafluoroxenate (XeF⁻
₅) ion. Permanganate can be solubilized in organic solvents, when deployed as its NBu⁺
₄ salt.

With exceptionally strong bases, quat cations degrade. They undergo Sommelet–Hauser rearrangement and Stevens rearrangement, as well as dealkylation under harsh conditions or in presence of strong nucleophiles, like thiolates. Quaternary ammonium cations containing N−C−C−H units can also undergo the Hofmann elimination and Emde degradation.

Quaternary ammonium salts are used as disinfectants, surfactants, fabric softeners, and as antistatic agents (e.g. in shampoos). In liquid fabric softeners, the chloride salts are often used. In dryer anticling strips, the sulfate salts are often used. Older aluminium electrolytic capacitors and spermicidal jellies also contain quaternary ammonium salts. Quats are also used in contraception formulations, veterinary products, diagnostic testing, vaccine production, and nasal formulations.