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)

Flash point:

132 °C

storage temp. 

2-8°C

solubility 

methanol: soluble1g/10 mL, clear to faintly turbid, colorless to very faintly yellow

pka

9.76±0.23(Predicted)

form 

Crystalline Powder or Crystals

color 

White to light beige

PH

7 (0.2g/l, H2O)

Odor

wh. 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.

InChIKey

OSDLLIBGSJNGJE-UHFFFAOYSA-N

LogP

3.270

CAS DataBase Reference

88-04-0(CAS DataBase Reference)

NIST Chemistry Reference

Chloroxylenol(88-04-0)

EPA Substance Registry System

4-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 Data

88-04-0(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 3830 mg/kg

MSDS

• Language:English Provider:4-Chloro-3,5-dimethylphenol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Chloro-3,5-dimethylphenol Usage And Synthesis

Chemical Properties

White or cream-colored crystals or crystalline powder with a characteristic phenolic odor. Volatile in steam.

Chemical Properties

4-Chloro-3,5-dimethylphenol is white or cream crystalline powder with a characteristic odour

Originator

Septiderm ,Fougera ,US,1960

Uses

4-Chloro-3,5-dimethylphenol is an antiseptic and germicide. Chloroxylenol is used for mildew prevention. Chloroxylenol is also an antibacterial; antiseptic (topical and urinary).

Uses

antibacterial, topical and urinary antiseptic

Uses

Antiseptic and germicide; for mildew prevention. Claimed to be about 60 times as potent as phenol.

Production Methods

Chloroxylenol is prepared by treating 3,5-dimethylphenol with chlorine or sulfuryl chloride (SO₂Cl₂).

Definition

ChEBI: 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.

Manufacturing Process

546 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 Function

Topical antiseptic; Disinfectant

General Description

The 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 Applications

4-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 Uses

Microbiocide: 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 name

BAR-FUNGAL PLUS®[C]; BIO SLIME®[C]; DESSON®; DETTOL®; ECOTRU®; ESPADOL®; HUSEPT®; HUSEPT EXTRA®; NIPACIDE®; OTTASEPT®[C]; OTTASEPT® EXTRA[C]; PCMX; RBA 777®

Clinical Use

p-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 Profile

Poison 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-.

Safety

Chloroxylenol 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

storage

Chloroxylenol 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 Methods

Crystallise the phenol from *benzene or toluene. [Beilstein 6 IV 3152.]

Incompatibilities

4-Chloro-3,5-dimethylphenol has been reported to be incompatible with nonionic surfactants and methylcellulose.

Regulatory Status

Included 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%.

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