Chloroxylenol

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Chloroxylenol
Kekulé, skeletal formula of chloroxylenol
Names
Preferred IUPAC name
4-Chloro-3,5-dimethylphenol[1]
Other names
para-Chloro-meta-xylenol, PCMX, 4-Chloro-3,5-dimethylphenol
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 [2]
alcohols
 soluble
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 (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.[2]

Synthesis

Other chlorine substituted phenols are contaminated with dioxins resulting from their synthesis. USEPA found chloroxylenol synthesis was not affected.[3][4]

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.[2] Chloroxylenol is used in a number of formulations and under a number of brand names, most notably Dettol.[5]

The World Health Organization lists a 4.8% solution of chloroxylenol as an essential medicine.

medical instruments.[7]

The use of chloroxylenol has been increasing due to the removal of hexachlorophene[2] and later triclosan and others from world markets.[8][4] 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

[3][4]

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.[3]

EU

Chloroxylenol is allowed in cosmetics up to 0.5%[4]

Antimicrobial properties

Chloroxylenol is most effective against

enzymes.[9][10][4] It is less effective than some other available agents.[11][9]
Testing has shown products containing chloroxylenol effective against the SARS-CoV-2 virus[12] and orthopoxviruses.[13]

Toxicology

Chloroxylenol is generally slightly to moderately

skin sensitizer.[8]

Related compounds

References

  1. ^ CID 2723 from PubChem
  2. ^
    ISBN 978-0-8247-9524-5. Archived
    from the original on 2017-09-23.
  3. ^ a b c d R.E.D Facts, Chloroxylenol, United States Environmental Protection Agency (EPA), September 1994.
  4. ^ a b c d e "Chloroxylenol - brand name list from Drugs.com" (PDF). www.industrialchemicals.gov.au. Archived from the original on 2017-08-28.
  5. ^ "Chloroxylenol - brand name list from Drugs.com". www.drugs.com. Archived (PDF) from the original on 2023-03-12.
  6. hdl:10665/325771
    . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  7. ^
    ISBN 9789241547659
    .
  8. ^ a b "Chemical Profile: Chloroxylenol". www.madesafe.org. 25 May 2023. Archived from the original on 2023-11-24.
  9. ^
    ISBN 9780323292627. Archived
    from the original on 2017-01-13.
  10. PMID 29939630
    .
  11. S2CID 205427305
    .
  12. PMID 32461067
    . Retrieved 2021-01-31.
  13. S2CID 43085296
    .

External links

Media related to Chloroxylenol at Wikimedia Commons

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