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Chloroxylenol

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Chloroxylenol
Kekulé, skeletal formula of chloroxylenol
Names
Systematic IUPAC name
4-Chloro-3,5-dimethylphenol[1]
Identifiers
3D model (JSmol)
1862539
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
  • CC1=CC(O)=CC(C)=C1Cl
Properties
C8H9ClO
Molar mass 156.61 g·mol−1
log P 3.377
Acidity (pKa) 9.76
Basicity (pKb) 4.24
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 (4-chloro-3,5-dimethylphenol) is an antimicrobial chemical compound used to control bacteria, algae, and fungi in adhesives, emulsions, paints, and wash tanks.[2] It is also commonly used in antibacterial soaps such as Dettol and ointments, such as the now discontinued Medicated Vaseline.[3] Studies have shown a low anti microbial activity which is enhanced by additives. Its antibacterial action is due to disruption of cell membrane potentials.[4]

Chloroxylenol is not significantly toxic to humans and other mammals, is practically non-toxic to birds, moderately toxic to freshwater invertebrates and highly toxic to fish.[2] It is a mild skin irritant and may trigger allergic reactions in some individuals. Cross sensitivity with chlorocresol is common.[3]

References

  1. ^ "chloroxylenol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 25 March 2005. Identification and Related Records. Retrieved 7 October 2011.
  2. ^ a b http://www.epa.gov/oppsrrd1/REDs/factsheets/3045fact.pdf
  3. ^ a b Ascenzi, Joseph M. (1996). "Chloroxylenol: an old-new antimicrobial". Handbook of disinfectants and antiseptics. New York: M. Dekker. ISBN 978-0-8247-9524-5.
  4. ^ Aly, R; Malbach, H (1988). "Comparative antibacterial efficacy of a 2-minute surgical scrub with chlorhexidine gluconate, povidone-iodine, and chloroxylenol sponge-brushes". American Journal of Infection Control. 16 (4): 173–7. doi:10.1016/0196-6553(88)90029-6. PMID 3189943. {{cite journal}}: More than one of |author= and |last1= specified (help)