4-Chloro-3,5-dimethylphenol

4-Chloro-3,5-dimethylphenol Basic information
Product Name:4-Chloro-3,5-dimethylphenol
Synonyms:Dettol, liquid antiseptic;Espadol;Husept extra;huseptextra;Nipacide mx;Nipacide PX;Ottasept;Ottasept extra
CAS:88-04-0
MF:C8H9ClO
MW:156.61
EINECS:201-793-8
Product Categories:DETTOL;Antibacterial agent;Preservative;Building Blocks;C6 to C8;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Phenols;Phenoles and thiophenoles;PCMX-PCMX;88-04-0
Mol File:88-04-0.mol
4-Chloro-3,5-dimethylphenol Structure
4-Chloro-3,5-dimethylphenol Chemical Properties
Melting point 114-116 °C(lit.)
Boiling point 246 °C
density 0.67 g/cm3
refractive index 1.5523 (estimate)
Fp 132 °C
storage temp. 2-8°C
solubility methanol: soluble1g/10 mL, clear to faintly turbid, colorless to very faintly yellow
pka9.76±0.23(Predicted)
form Crystalline Powder or Crystals
color White to light beige
PH7 (0.2g/l, H2O)
Odorwh. cryst. or cryst. powd., char. phenolic odor
Water Solubility 0.3 g/L (20 ºC)
Merck 14,2176
BRN 1862539
Stability:Stable. Incompatible with strong oxidizing agents.
InChIKeyOSDLLIBGSJNGJE-UHFFFAOYSA-N
LogP3.270
CAS DataBase Reference88-04-0(CAS DataBase Reference)
NIST Chemistry ReferenceChloroxylenol(88-04-0)
EPA Substance Registry System4-Chloro-3,5-dimethylphenol (88-04-0)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/38-43
Safety Statements 24-37
RIDADR UN 3077 9/PG 3
WGK Germany 1
RTECS ZE6850000
Hazard Note Irritant
TSCA Yes
HazardClass 9
PackingGroup III
HS Code 29081000
Hazardous Substances Data88-04-0(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 3830 mg/kg
MSDS Information
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4-Chloro-3,5-dimethylphenol English
SigmaAldrich English
ACROS English
ALFA English
4-Chloro-3,5-dimethylphenol Usage And Synthesis
Chemical PropertiesWhite or cream-colored crystals or crystalline powder with a characteristic phenolic odor. Volatile in steam.
Chemical Properties4-Chloro-3,5-dimethylphenol is white or cream crystalline powder with a characteristic odour
OriginatorSeptiderm ,Fougera ,US,1960
Usesantibacterial, topical and urinary antiseptic
UsesAntiseptic and germicide; for mildew prevention. Claimed to be about 60 times as potent as phenol.
Uses4-Chloro-3,5-dimethylphenol is an antiseptic and germicide. Chloroxylenol is used for mildew prevention. Chloroxylenol is also an antibacterial; antiseptic (topical and urinary).
DefinitionChEBI: 4-chloro-3,5-dimethylphenol is a member of the class of phenols that is 3,5-xylenol which is substituted at position 4 by chlorine. It is bactericidal against most Gram-positive bacteria but less effective against Staphylococci and Gram-negative bacteria, and often inactive against Pseudomonas species. It is ineffective against bacterial spores. It has a role as an antiseptic drug, a disinfectant and a molluscicide. It is a member of phenols and a member of monochlorobenzenes. It is functionally related to a 3,5-xylenol.
Production MethodsChloroxylenol is prepared by treating 3,5-dimethylphenol with chlorine or sulfuryl chloride (SO2Cl2).
Manufacturing Process546 g of intermediate xylenol fraction having a crystallizing point of 45°C mixed with an equal weight of m-5-xylenol are placed in a suitable vessel, equipped with stirring gear, and 273 g of sulfuryl chloride are added slowly. The temperature rises in the course of the reaction to about 40°C. When all the sulfuryl chloride is added the reaction mixture is heated to 80°C and theacid gases removed as far as possible by air-blowing or any other suitable means. On cooling a quantity of the required chlor-xylenol separates out and is removed from the mother liquor. Further quantities of the material required can be isolated by vacuum distillation of the mother liquors and further crystallization. In all, 200 to 208 g of material substantially 2-chlor-m-5- xylenol can be obtained having a melting point of 112°C to 115°C. The material can be purified if desired by crystallization from a solvent such as a hydrocarbon.
Therapeutic FunctionTopical antiseptic; Disinfectant
General DescriptionThe degradation of 4-chloro-3,5-dimethylphenol (PCMX) by Fenton-like process using nanoparticulate zero-valent iron (nZVI) and hydrogen peroxide (H2O2) was studied.
Pharmaceutical Applications4-Chloro-3,5-dimethylphenol is a common constituent of many proprietary disinfectants used for skin and wound disinfection.
As a pharmaceutical excipient, 4-Chloro-3,5-dimethylphenol is commonly used in low concentrations as an antimicrobial preservative in topical formulations such as creams and ointments. 4-Chloro-3,5-dimethylphenol is also used in a number of cosmetic formulations.
Therapeutically, 4-Chloro-3,5-dimethylphenol has been investigated as a treatment for acne vulgaris, for treating infected root canals, and as an antifungal agent when impregnated into medical devices. 4-Chloro-3,5-dimethylphenol is included in drug products approved for topical antifungal, topical acne and topical dandruff/seborrheic dermatitis/psoriasis treatments.

Agricultural UsesMicrobiocide: 4-Chloro-3,5-dimethylphenol was first registered in the U.S. for use as a fungicide and is now applied as an antimicrobial for control of bacteria, algae and fungi in adhesives, emulsions, paints and wash tanks. It is registered for use in household and domestic dwellings, laundry equipment, bathrooms, diaper pails and in industrial water and aqueous systems. Not listed for use in EU countries. Registered for use in the U.S. There are 64 global suppliers.
Trade nameBAR-FUNGAL PLUS®[C]; BIO SLIME®[C]; DESSON®; DETTOL®; ECOTRU®; ESPADOL®; HUSEPT®; HUSEPT EXTRA®; NIPACIDE®; OTTASEPT®[C]; OTTASEPT® EXTRA[C]; PCMX; RBA 777®
Clinical Usep-Chloro-m-xylenol (PC-MX; Metasep) is a nonirritating antiseptic agent with broad-spectrum antibacterial and antifungal properties. It is marketed in a 2% concentration as a shampoo. It has also been used topically for the treatment of tinea (ringworm) infections such as athlete s foot (tinea pedis) and jock itch (tinea cruris).
Safety ProfilePoison by intraperitoneal route. Moderately toxic by ingestion. An experimental teratogen. An eye irritant. An antimicrobial agent. See also CHLOROPHENOLS and CHLORINATED HYDROCARBONS, AROMATIC. When heated to decomposition it emits toxic fumes of Cl-.
SafetyChloroxylenol is generally regarded as a relatively nontoxic and nonirritant material when used as an excipient in topical products. However, chloroxylenol has been placed in Toxicity Category I for eye irritation effects. In addition, allergic skin reactions have been reported. Taken orally, chloroxylenol is mildly toxic and ingestion of a chloroxylenol-containing disinfectant product has been associated with reports of fatal or severe instances of selfpoisoning.
LD50 (mouse, IP): 0.115 g/kg
LD50 (rat, dermal): >2.0 g/kg
LD50 (rat, oral): 3.83 g/kg


storageChloroxylenol is stable at normal room temperature, but is volatile in steam. Contact with natural rubber should be avoided. Aqueous solutions of chloroxylenol are susceptible to microbial contamination and appropriate measures should be taken to prevent contamination during storage or dilution. Chloroxylenol should be stored in polyethylene, mild steel or stainless steel containers, which should be well-closed and kept in a cool, dry place. Chloroxylenol does not absorb at wavelengths >290 nm and has been reported to be stable to sunlight for up to 24 hours.
Purification MethodsCrystallise the phenol from *benzene or toluene. [Beilstein 6 IV 3152.]
Incompatibilities4-Chloro-3,5-dimethylphenol has been reported to be incompatible with nonionic surfactants and methylcellulose.
Regulatory StatusIncluded in the FDA Inactive Ingredients Database (otic preparations; topical creams and emulsions). Included in nonparenteral medicines licensed in the UK. Approved in Europe as a preservative in cosmetics with a maximum authorized concentration of 0.5%.
Formaldehyde, reaction products with 4-chloro-3,5-dimethylphenol and diethanolamine Quaternary ammonium compounds, di-C8-12-alkyldimethyl, salts with 4-chloro-3,5-dimethylphenol DIMETHYLTHEXYLSILYL CHLORIDE 4-chloro-3,5-dimethylphenol, triester with boric acid 4-chloro-3,5-xylyloxyacetic acid 3-AMINO-4-(4-CHLORO-3,5-DIMETHYLPHENOXY)BENZOTRIFLUORIDE 2,4,6-trichloro-3,5-dimethylphenol 2,4-DICHLORO-5-ETHYL-3-METHYLPHENOL N1,N1-DIMETHYL-2-(4-CHLORO-3,5-DIMETHYLPHENOXY)-5-(TRIFLUOROMETHYL)ANILINE N-[2-(4-CHLORO-3,5-DIMETHYLPHENOXY)-5-(TRIFLUOROMETHYL)PHENYL]-N'-(1,2,2-TRICHLOROVINYL)UREA N1-[2-(4-CHLORO-3,5-DIMETHYLPHENOXY)-5-(TRIFLUOROMETHYL)PHENYL]-2,3,3-TRICHLOROACRYLAMIDE 2,4,6-TRICHLORO-3-ETHYL-5-METHYL-PHENOL O-phthalaldehyde,4-chloro-3,5-dimethylphenol N1-[2-(4-CHLORO-3,5-DIMETHYLPHENOXY)-5-(TRIFLUOROMETHYL)PHENYL]-2-CHLOROACETAMIDE 3-(4-CHLORO-3,5-DIMETHYLPHENOXYMETHYL)-5-[(O-ETHYL-N-ISOPROYLPHOSPHONYL)THIOMETHYL]-1,2,4-OXADIAZOLE Quaternary ammonium compounds, benzyl-C12-14-alkyldimethyl, salts with 4-chloro-3,5-dimethylphenol 2-(4'-CHLORO-3',5'-DIMETHYL- PHENOXY) ETHANOL (CHLOROXYLENOL) POWDER BP.

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