Chloroxylenol

Chloroxylenol, also known as para-chloro-meta-xylenol (PCMX), is a chlorine substituted phenol with a white to off-white appearance and a phenolic odor. The discovery of chloroxylenol was the result of efforts to produce improved antiseptics that began at the end of the 1800s. First synthesized in Germany in 1923, it was borne out of the study of coal tar components that began a decade earlier.

Synthesis
Other chlorine substituted phenols are contaminated with dioxins resulting from their synthesis. USEPA found chloroxylenol synthesis was not affected.

Uses
Formulations containing chloroxylenol are used in hospitals and households as antiseptics, disinfectants, and sanitizers. It is commonly used in antibacterial soaps, wound-cleansing, and other household antiseptic applications. Chloroxylenol is used in a number of formulations and under a number of brand names, most notably Dettol.

The World Health Organization lists a 4.8% solution of chloroxylenol as an essential medicine. When diluted, this chloroxylenol preparation is used as an antiseptic and disinfectant, and for skin disinfection. Diluted with alcohol, it is suitable for disinfecting medical instruments.

The use of chloroxylenol has been increasing due to the removal of hexachlorophene and later triclosan and others from world markets. It is currently used for control of bacteria, algae, and fungi in:
 * Adhesive and sealant products
 * Construction products
 * Lubricant and grease products
 * Paint and coating products
 * Plastic and polymer products
 * wash tanks
 * diaper pails
 * laundry equipment
 * bedding
 * pet living quarters
 * hospitals
 * Personal care products
 * Cleaning and furniture care products
 * Fabric, textile and leather products
 * Ink, toner and colorant products

United States
Chloroxylenol was first introduced to the USA in 1959. Chloroxylenol containing products must not be used in any manner that allows contamination of water.

EU
Chloroxylenol is allowed in cosmetics up to 0.5%

Antimicrobial properties
Chloroxylenol is most effective against gram-positive bacteria. It works by disruption of the cell wall and stopping the function of enzymes. It is less effective than some other available agents. Testing has shown products containing chloroxylenol effective against the SARS-CoV-2 virus and orthopoxviruses.

Toxicology
Chloroxylenol is generally slightly to moderately toxic to humans (but causes severe eye irritation), is practically non-toxic to birds, toxic to fish, and moderately toxic to freshwater invertebrates. The European Union considers it to be a skin sensitizer.

Related compounds

 * 4-chloro-3-methylphenol (PCMC) – similar use / similar structure
 * 2-Chloro-m-cresol – Structural similarity