Chloroxylenol

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]
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 (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, when scientists gradually realized that more substituted and more lipophylic phenols are less toxic, less irritant and more powerful.[3] First synthesized in Germany in 1923, it was borne out of the study of coal tar components that began a decade earlier.[2]

  1. ^ CID 2723 from PubChem
  2. ^ a b Cite error: The named reference Ascenzi was invoked but never defined (see the help page).
  3. ^ 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.