Chloroxylenol

Title: Chloroxylenol
CAS Registry Number: 88-04-0
CAS Name: 4-Chloro-3,5-dimethylphenol
Additional Names: p-chloro-m-xylenol; 4-chloro-3,5-xylenol; parachlorometaxylenol; 2-chloro-m-xylenol; 2-chloro-5-hydroxy-m-xylene; 2-chloro-5-hydroxy-1,3-dimethylbenzene
Trademarks: Benzytol; Dettol (Reckitt & Colman)
Molecular Formula: C8H9ClO
Molecular Weight: 156.61
Percent Composition: C 61.35%, H 5.79%, Cl 22.64%, O 10.22%
Literature References: Prepd by treating 3,5-dimethylphenol with Cl2 or SO2Cl2: Lesser, Gad, Ber. 56, 974, 976 (1923); von Auwers et al., Chem. Zentralbl. 1924, II, 2267, C.A. 19, 2339 (1925); Gladden, Cocker, US 2350677 (1944).
Properties: Crystals from benzene, mp 115.5°. Phenolic odor. Volatile with steam. bp 246°. One gram dissolves in 3 liters of water at 20°. More stable in hot water. Soluble in 1 part of 95% alcohol, ether, benzene, terpenes, fixed oils, in solns of alkali hydroxides.
Melting point: mp 115.5°
Boiling point: bp 246°
Use: Antiseptic and germicide; for mildew prevention. Claimed to be about 60 times as potent as phenol.
Therap-Cat: Antibacterial; antiseptic (topical and urinary).
Therap-Cat-Vet: Antiseptic (topical).
Keywords: Antiseptic/Disinfectant; Phenols.
Chlorozotocin Chlorphenesin Chlorphenesin Carbamate Chlorpheniramine Chlorphenoxamide

Chloroxylenol
Kekulé, skeletal formula of chloroxylenol
Identifiers
CAS number 88-04-0 YesY
PubChem 2723
ChemSpider 21106017 YesY
UNII 0F32U78V2Q YesY
EC number 201-793-8
KEGG D03473 YesY
MeSH chloroxylenol
ChEBI CHEBI:34393
ChEMBL CHEMBL398440 N
RTECS number ZE6850000
ATC code D08AE05
Beilstein Reference 1862539
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C8H9ClO
Molar mass 156.61 g mol−1
Melting point 114 to 116 °C; 237 to 241 °F; 387 to 389 K
log P 3.377
Acidity (pKa) 9.76
Basicity (pKb) 4.24
Hazards
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
GHS hazard statements H302, H315, H317, H319
GHS precautionary statements P280, P305+351+338
EU Index 604-038-00-4
EU classification Harmful Xn
R-phrases R22, R36/38, R43
S-phrases (S2), S24, S37
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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 and household antiseptics such as Dettol liquid and cream, 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]