Chloroxylenol

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Chloroxylenol
Kekulé, skeletal formula of chloroxylenol
Kekulé, skeletal formula of chloroxylenol
Names
Preferred IUPAC name
4-Chloro-3,5-dimethylphenol
Other names
para-Chloro-meta-xylenol, PCMX, 4-Chloro-3,5-dimethylphenol, CHO
Identifiers
3D model (JSmol)
1862539
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.631 Edit this at Wikidata
EC Number
  • 201-793-8
KEGG
MeSH chloroxylenol
RTECS number
  • ZE6850000
UNII
  • InChI=1S/C8H9ClO/c1-5-3-7(10)4-6(2)8(5)9/h3-4,10H,1-2H3 ☒N
    Key: OSDLLIBGSJNGJE-UHFFFAOYSA-N ☒N
  • InChI=1/C8H9ClO/c1-5-3-7(10)4-6(2)8(5)9/h3-4,10H,1-2H3
    Key: OSDLLIBGSJNGJE-UHFFFAOYAY
  • Cc1cc(O)cc(C)c1Cl
Properties
C8H9ClO
Molar mass 156.61 g·mol−1
Melting point 115 °C (239 °F; 388 K)
Boiling point 246 °C (475 °F; 519 K)
300 mg/L [1]
Solubility in alcohols soluble
Solubility in Ethers soluble
Solubility in Benzene soluble
log P 3.377
Acidity (pKa) 9.76
Basicity (pKb) 4.24
Pharmacology
D08AE05 (WHO)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302, H315, H317, H319
P280, P305+P351+P338
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Chloroxylenol, also known as para-chloro-meta-xylenol, is an organic compound with the formula (CH3)2ClC6H2OH. It is a chlorine-substituted xylenol. The compound is a colorless solid although impure samples can appear off-white. It has a phenolic odor. It is a common antiseptic.[2]


Uses

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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.[2] Chloroxylenol is used in a number of formulations and under a number of brand names including Dettol.[3]

It is on the World Health Organization's List of Essential Medicines.[4] 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.[5]

Chloroxylenol has been substituted for hexachlorophene and triclosan, which have been removed from world markets.[6][7] It is currently used for control of bacteria, algae, and fungi in:[8][7]

  • 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

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Chloroxylenol was first introduced to the United States in 1959. Chloroxylenol containing products must not be used in any manner that allows contamination of water.[8]

European Union

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The European Union allows chloroxylenol in cosmetics up to 0.5%.[7][9]

Antimicrobial properties

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Chloroxylenol is most effective against gram-positive bacteria.[5] It works by disruption of the cell wall and stopping the function of enzymes.[10][11][7] It is less effective than some other available agents.[2][10] Testing has shown products containing chloroxylenol effective against the SARS-CoV-2 virus[12] and orthopoxviruses.[13] No evidence for bacterial resistance has been investigated but not confirmed.[14]

Synthesis

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Chloroxylenol is produced by chlorination of the corresponding xylenol.[15]

Toxicology

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It is " is safe as used in cosmetics".[16] 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.[8] The European Union considers it to be a skin sensitizer.[6]

Chloroxylenol may also be harmful to smaller vertebrates, especially cats. Phenolic compounds are of particular concern to felines because cats are unable to fully metabolize them. A cat may swallow the product by licking its paws after it has come into contact with it.[17][18] Products containing chloroxylenol such as Dettol have been previously administered with a spray bottle on unwanted pests or invasive species such as cane toads, which die shortly after being sprayed with the phenolic compound. The use of chloroxylenol-containing Dettol as an agent for pest control was banned in Western Australia by the Department of Environment and Conservation in 2011.[19]

History

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The discovery of chloroxylenol was the result of efforts to produce improved antiseptics that began at the end of the 1800s, when it was realized that more substituted and more lipophilic phenols are less toxic, less irritating, and more powerful.[20] First synthesized in Germany in 1923, it was born out of the study of coal tar components that began a decade earlier.[1]

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References

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  1. ^ a b Ascenzi JM (1996). "Chloroxylenol: an old-new antimicrobial". Handbook of disinfectants and antiseptics. New York: M. Dekker. ISBN 978-0-8247-9524-5. Archived from the original on 23 September 2017.
  2. ^ a b c Digison MB (2007). "A review of anti-septic agents for pre-operative skin preparation". Plastic Surgical Nursing. 27 (4): 185–9, quiz 190–1. doi:10.1097/01.psn.0000306182.50071.e2. PMID 18165724. S2CID 205427305.
  3. ^ "Chloroxylenol - brand name list from Drugs.com". www.drugs.com. Archived (PDF) from the original on 12 March 2023.
  4. ^ World Health Organization (2025). The selection and use of essential medicines, 2025: WHO Model List of Essential Medicines, 24th list. Geneva: World Health Organization. doi:10.2471/B09474. hdl:10665/382243. License: CC BY-NC-SA 3.0 IGO.
  5. ^ a b World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 324. hdl:10665/44053. ISBN 9789241547659.
  6. ^ a b "Chemical Profile: Chloroxylenol". www.madesafe.org. 25 May 2023. Archived from the original on 24 November 2023.
  7. ^ a b c d "Chloroxylenol - brand name list from Drugs.com" (PDF). www.industrialchemicals.gov.au. Archived from the original on 28 August 2017.
  8. ^ a b c R.E.D Facts, Chloroxylenol, United States Environmental Protection Agency (EPA), September 1994.
  9. ^ "Cosmetic Products Regulation, Annex V - Allowed Preservatives". echa.europa.eu.
  10. ^ a b Mahon CR, Lehman DC, Manuselis G Jr (2014). Textbook of Diagnostic Microbiology (5 ed.). Elsevier Health Sciences. p. 67. ISBN 9780323292627. Archived from the original on 13 January 2017.
  11. ^ Bednarek RS, Nassereddin A, Ramsey ML (2021). "Skin Antiseptics". StatPearls. StatPearls. PMID 29939630.
  12. ^ Ijaz K, Whitehead K, Srinivasan V, Jones C, Nims R, Charlesworth B (24 May 2020). "Microbicidal actives with virucidal efficacy against SARS-CoV-2". American Journal of Infection Control. 48 (8): 972–973. doi:10.1016/j.ajic.2020.05.015. PMC 7246051. PMID 32461067. Retrieved 31 January 2021.
  13. ^ Butcher W, Ulaeto D (2005). "Contact inactivation of orthopoxviruses by household disinfectants". Journal of Applied Microbiology. 99 (2). Wiley: 279–284. doi:10.1111/j.1365-2672.2005.02601.x. ISSN 1364-5072. PMID 16033458. S2CID 43085296.
  14. ^ Maillard JY (2022). "Impact of benzalkonium chloride, benzethonium chloride and chloroxylenol on bacterial antimicrobial resistance". Journal of Applied Microbiology. 133 (6): 3322–3346. doi:10.1111/jam.15739. PMC 9826383. PMID 35882500.
  15. ^ An overview of chlorination methods: Mostafa MA, Bowley RM, Racys DT, Henry MC, Sutherland A (2017). "Iron(III)-Catalyzed Chlorination of Activated Arenes". The Journal of Organic Chemistry. 82 (14): 7529–7537. doi:10.1021/acs.joc.7b01225. PMID 28661157.
  16. ^ Cherian P, Bergfeld WF, Belsito DV, Cohen DE, Klaassen CD, Liebler DC, et al. (2023). "Chloroxylenol". International Journal of Toxicology. 42 (3_suppl): 22S – 23S. doi:10.1177/10915818231204263. PMID 37769700.
  17. ^ "Nine things you didn't know could poison your pet". Archived from the original on 24 February 2022.
  18. ^ Dettol liquid at drugs.com Archived 2015-09-24 at the Wayback Machine
  19. ^ Narelle Towie (23 May 2009). "Cane toad poison banned". Perth Now. Archived from the original on 15 January 2013. Retrieved 2 February 2013.
  20. ^ de Solis NM (1993). Effect of plasmids that confer preservative-resistance on the performance of bacteria in preservative efficacy tests (Doctoral thesis). University College London. p. 31.
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