This paper investigates the reaction between pool chlorinators and gasoline. In particular, the propensity for self-ignition and the resulting chemical products were studied. An organic pool chlorinator was combined with gasoline in varying proportions in an attempt to form a hypergolic mixture. None of the combinations resulted in self-ignition, but larger quantities of chlorinator produced vigorous light-colored smoke and a solid mass containing isocyanuric acid and copper chloride. Additionally, the chlorinating abilities of different commercially available pool chlorinators were explored. When Ca(ClO)2 and sodium dichloro-s-triazinetrione-based chlorinators were used, the presence of gasoline was still visible after 10 days, despite limited chlorination. The trichloro-s-triazinetrione-based chlorinator, however, caused efficient chlorination of the C2- and C3-alkylbenzenes, making gasoline no longer identifiable. Abstract published by arrangement with John Wiley & Sons.