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Synlett 2014; 25(4): 599-600
DOI: 10.1055/s-0033-1340488
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© Georg Thieme Verlag Stuttgart · New York

Cetylpyridinium Chloride

Oksana Paley
Chemical Faculty, Uzhgorod National University, Fedynets St. 53, 88000 Uzhgorod, Ukraine   Email: oksanapaley@mail.ru
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Publication History

Publication Date:
13 January 2014 (online)

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Introduction

Cetylpyridinium chloride (CPC; IUPAC name: 1-hexadecylpyridinium chloride) is a cationic quaternary ammonium salt with a molar mass of 339.99 g/mol and a melting point of 77 °C (80–83 °C for its monohydrate form). These beige flakes are insoluble in acetone, acetic acid, and ethanol but can be solved in water.

CPC is commercially available and can be synthesized by the reaction of cetyl chloride with pyridine[1a] and by alkylation of pyridine with cetyl dichlorophosphate.[1b] If swallowed or inhaled, it is toxic, and it is irritating to the eyes, respiratory system, and skin. However, it is also an antiseptic that kills bacteria and other microorganisms.[2] Therefore, it is effective in preventing dental plaque and in reducing gingivitis.[3] CPC is widely used in industrial and commercial formulations, including disinfectants, cosmetics, and pharmaceuticals. Hence, its accurate determination is necessary.[4]

The application of CPC in organic synthesis and analytical chemistry includes use as a phase-transfer catalyst,[5] modification of surface of sorbents,[6] synthesis of mesoporous materials,[7] preparation of nanoparticles,[8] formation of turbid gels,[9] determination of anionic surfactants[10]/mercury[11]/ thallium,[12] and the detection of 2,4,6-trinitrotoluene.[13] CPC shows an inhibitory action on the corrosion of mild steel.[14]