59-50-7

white or pink crystals

antiinfectant

Disinfectant; pharmaceutic aid (preservative).

A pinkish to white crystalline solid with a phenolic odor. Melting point 64-66°C. Shipped as a solid or in a liquid carrier. Soluble in aqueous base. Toxic by ingestion, inhalation or skin absorption. Used as an external germicide. Used as a preservative in paints and inks.

CHLOROCRESOL(59-50-7)S are incompatible with bases, acid chlorides, acid anhydrides, and oxidizing agents. Corrodes steel, brass, copper and copper alloys .

Hygroscopic. Soluble in aqueous base.

Irritant to skin.

Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Chlorinated phenol fungicide, microbiocide, and germicide used to control bacteria, yeasts, and fungi.

Combustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions) if breathing has stopped, and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Do not induce vomiting when formulations containing petroleum solvents are ingested. Otherwise, give large quantities of water and induce vomiting. Do not make an unconscious person vomit.

UN2669 Chlorocresols solution, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN3437 Chlorocresols solid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Chlorocresols react with boranes, alkalies, aliphatic amines, amides, nitric acid, sulfuric acid. Contact with oxidizing agents may cause a fire and explosion hazard. Heat produces phosgene, hydrogen chloride and chlorine gases. Corrosive to aluminum, copper, tin, and other chemically active metals.

A good candidate for rotary kiln incineration at a temperature range of 820 to 1600C and residence times of seconds for liquids and gases, and hours for solids.

Colorless, white, or pinkish crystals with a slight phenolic odor. On exposure to air it slowly becomes light brown.

ChEBI: 4-chloro-m-cresol is a hydroxytoluene that is 3-methylphenol which is substituted by a chlorine at position 4. A ryanodine receptor agonist. It has a role as a ryanodine receptor agonist, an antimicrobial agent and a disinfectant. It is a hydroxytoluene and a member of monochlorobenzenes.

Chlorocresol is prepared by the chlorination of m-cresol.

Chlorocresol is used as an antimicrobial preservative in cosmetics and pharmaceutical formulations. It is generally used in concentrations up to 0.2% in a variety of preparations except those intended for oral administration or that contact mucous membrane. Chlorocresol is effective against bacteria, spores, molds, and yeasts; it is most active in acidic media. Preservative efficacy may be reduced in the presence of some other excipients, particularly nonionic surfactants.

Chlorocresol is used as a preservative in a variety of topical preparations, such as corticosteroid creams and moisturizers and in disinfectants and detergents. Three case reports implicate chlorocresol as a cause of Cou; however, whether this is due to an immunological cause is uncertain.
Walker et al. report a patient who experienced localized Cou to a number of topical medicaments and moisturizers within 30 minutes of application. Patch tests of chlorocresol and her own preparations containing chlorocresol applied for just 30 minutes produced marked urticarial responses.
A woman working in an aviary developed eyelid edema and erythema every time she used two specific disinfectants. Open and skin prick testing to 10%, but not 1%, chlorocresol was positive in this case and negative in 10 controls. This patient also experienced eyelid involvement as well as local reactions to the testing, both with superficial necrosis. Freitas et al. acknowledged that it was unusual on both aspects: for such a high concentration to be required to elicit an urticarial reaction and for superficial necrosis to occur.
A case of simultaneous delayed and immediate hypersensitivity has also been reported. Goncalo et al. report a 35-year-old laboratory worker exposed to chlorocresol in both detergents and corticosteroid creams. Patch testing was positive and the patient was diagnosed with allergic contact dermatitis to chlorocresol, which was present in numerous products. Open and skin prick testing to 1% and 5% chlorocresol were positive after 20 minutes. Ten controls were also tested, all were negative to the 1% formulation, although six were positive to 5%,[48] suspicious for a nonimmunological Cou.

Chlorocresol is used primarily as a preservative in topical pharmaceutical formulations but has also been used in nebulized solutions and ophthalmic and parenteral preparations. It should not, however, be used in formulations for intrathecal, intracisternal, or peridural injection.
Chlorocresol is metabolized by conjugation with glucuronic acid and sulfate and is excreted in the urine, mainly as the conjugate, with little chlorocresol being excreted unchanged. Although less toxic than phenol, chlorocresol may be irritant to the skin, eyes, and mucous membranes, and has been reported to cause some adverse reactions when used as an excipient.
Sensitization reactions may follow the prolonged application of strong solutions to the skin, although patch tests have shown that chlorocresol is not a primary irritant at concentrations up to 0.2%. Chlorocresol is recognized as a rare cause of allergic contact dermatitis. Cross sensitization with the related preservative chloroxylenol has also been reported. At concentrations of 0.005% w/v, chlorocresol has been shown to produce a reversible reduction in the ciliary movement of human nasal epithelial cells in vitro, and at concentrations of 0.1% chlorocresol produces irreversible ciliostasis; therefore it should be used with caution in nasal preparations. However, a clinical study in asthma patients challenged with chlorocresol or saline concluded that preservative might be used safely in nebulizer solution.
Chlorocresol is approved as safe for use in cosmetics in Europe at a maximum concentration of 0.2%, although not in products intended to come in contact with mucous membranes.
Chlorocresol at a concentration as low as 0.05% produces ocular irritation in rabbits. Despite such reports, chlorocresol has been tested in ophthalmic preparations.
When used systemically, notably in a heparin injection preserved with chlorocresol 0.15%, delayed irritant and hypersensitivity reactions attributed to chlorocresol have been reported.
LD₅₀ (mouse, IV): 0.07 g/kg
LD₅₀ (mouse, oral): 0.6 g/kg
LD₅₀ (mouse, SC): 0.36 g/kg
LD₅₀ (rabbit, dermal): >5 g/kg
LD₅₀ (rat, dermal): >2 g/kg
LD₅₀ (rat, oral): 1.83 g/kg
LD₅₀ (rat, SC): 0.4 g/kg

Biological. When p-chloro-m-cresol was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, significant biodegradation with rapid adaptation was observed. At concentrations of 5 and 10 mg/L, 78 and 76% biodegradation, respectively, were observed after 7 d (Tabak et al., 1981).
Chemical/Physical. At influent concentrations (pH 3.0) of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC adsorption capacities were 122, 63, 32, and 17 mg/g, respectively. At pH 5.5 and pH 9.0 at influent concentrations of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC adsorption capacities were 124, 85, 58, and 40 mg/g and 99, 38, 15, and 5.5 mg/g, respectively (Dobbs and Cohen, 1980).

Chlorocresol is stable at room temperature but is volatile in steam. Aqueous solutions may be sterilized by autoclaving. On exposure to air and light, aqueous solutions may become yellow colored. Solutions in oil or glycerin may be sterilized by heating at 1608℃ for 1 hour. The bulk material should be stored in a well-closed container, protected from light, in a cool, dry place.

Crystallise the phenol from pet ether or *C6H6. [Beilstein 6 H 381, 6 I 187, 6 II 355, 6 III 1315, 6 IV 2064.]

Included in the FDA Inactive Ingredients Database (topical creams and emulsions). Included in nonparenteral and parenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.
In Europe, chlorocresol is approved for use in cosmetics at a maximum concentration of 0.2%; however, it is prohibited for use in products intended to come into contact with mucous membranes. In Japan, use of chlorocresol in cosmetics is restricted to a level of 0.5 g/100 g.