4-Chloro-3,5-dimethylphenol

156.61

156.61

215-316-6

0F32U78V2Q

756683|4971

DTXSID0032316

Crystals from benzene

D08AE05|D - Dermatologicals

2908199090

20.2

2

white to off-white crystalline powder

1.2±0.1 g/cm3

115 °C

246 °C

105.9±25.9 °C

1.558

0.3 g/L (20 ºC)

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

1.8X10-3 mm Hg at 25 deg C (est)

LD50 orally in Rabbit: 3830 mg/kg

Phenolic odor

pH = 6.45 at 20 °C after dispersion in distilled water

Henry's Law constant = 5.1X10-7 atm-cu m/mol at 25 °C (est)

pka = 9.7

Chloroxylenol is stable when exposed to sunlight and humidity from ambient storage over 24 hours. It is also stable at elevated temperatures (54 °C). Choroxylenol is hydrolytically stable.|Hydroxyl radical reaction rate constant = 6.7X10-11 cu cm/molec-sec at 25 °C (est)

At ambient temperature, a 25% solution of chloroxylenol in isopropanol is not corrosive to stainless steel or aluminum. Brass is slightly affected as is mild steel. Mild steel is slightly affected by isopropanol alone.

UN 3077 9/PG 3

1

R22;R36/38;R43

S24-S37

ZE6850000

Xn:Harmful

Stable. Incompatible with strong oxidizing agents.

P280-P305 + P351 + P338

H302-H315-H317-H319

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.|Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.|Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it.

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: chloroxylenol is included in topical acne drug products.|Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: chloroxylenol is included in dandruff/seborrheic dermatitis/psoriasis drug products..|Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: chloroxylenol is included in topical antifungal drug products.

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Chloroxylenol. EPA 738-R-94-032 September 1994. The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of February 7, 2006: http://www.epa.gov/pesticides/reregistration/status.htm]

|Warning|H302 (99.91%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, and P501|Aggregated GHS information provided by 1064 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]

If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label.|After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash.

Wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.|Indoor Applications. If the label directions permit, leave all windows open and fans operating after the application is completed. If the pesticide product is only effective in an unventilated (sealed) room or house, do not stay there. Put all pets outdoors, and take yourself any your family away from treated areas for at least the length of time prescribed on the label. Apply most surface sprays only to limited areas such as cracks; don't treat entire floors, walls, or ceilings. Don't let pesticides get on any surfaces that are used for food preparation. Wash any surfaces that may have pesticide residue before placing food on them.|Indoor Applications. When using total release foggers to control pests, use no more than the amount needed and to keep foggers away from ignition sources (ovens, stoves, air conditioners, space heaters, and water heaters, for example). Foggers should not be used in small, enclosed places such as closets and cabinets or under tables and counters.|Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face.

Chloroxylenol /is listed as one of/ common contact allergens /in/ antiseptics. /from Table/

As chloroxylenol is predominantly employed as an active ingredient in various liquids or creams as cleaners, disinfectants, or antiseptics that are generally designed to be used topically, it is widely accepted that the use of such liquids - when used appropriately - is unlikely to present a sufficient volume that could be ingested to cause any medical problems. In the event of accidental eye contact, was with Luke warm water. Chloroxylenol is known to have a low systemic toxicity, even at dosage levels many times higher that those likely to be absorbed during normal usage of the agent.

LD50 Rat oral 3830 mg/kg|LD50 Mouse ip 115 mg/kg|LD50 Rat dermal >2.0 g/kg

One study determined the protein binding of chloroxylenol to be approximately 85.2% +/- 2.32% for serum albumin and 89.8% +/- 2.99% for whole human serum.

Chloroxylenol's production and use as an antibacterial, germicide, antiseptic and in mildew prevention(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,400(SRC), determined from a log Kow of 3.27(2) and a regression-derived equation(3), indicates that chloroxylenol is expected to have low mobility in soil(SRC). Volatilization of chloroxylenol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.1X10-7 atm-cu m/mol(SRC), derived using a fragment constant estimation method(4). Chloroxylenol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Degradation of chloroxylenol appears to be slower than other phenol derivatives(5,6). Studies in sewage showed 95-80% of the original compound remaining after 2 days and 60-70% remaining after 7 days(5). This is consistent with other studies that showed less than 40% degradation in activated sludge over 7 days(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,400(SRC), determined from a log Kow of 3.27(2) and a regression-derived equation(3), indicates that chloroxylenol is expected to adsorb to suspended solids and sediment(SRC). Volatilization of chloroxylenol from water surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.1X10-7 atm-cu m/mol(SRC) derived using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 66(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Degradation of chloroxylenol appears to be slower than other phenol derivatives(7,8). Studies in sewage showed 80-95% of the original compound remaining after 2 days and 60-70% remaining after 7 days(7). This is consistent with other studies that showed less than 40% degradation in activated sludge after 7 days(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chloroxylenol, which has an estimated vapor pressure of 1.8X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase chloroxylenol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 6 hours(SRC), calculated from its rate constant of 6.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Chloroxylenol does not contain chromophores that absorb at wavelengths >290 nm(4) and has been reported to be stable to sunlight for up 24 hours(5).

The rate constant for the vapor-phase reaction of chloroxylenol with photochemically-produced hydroxyl radicals has been estimated as 6.7X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5.8 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Chloroxylenol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Chloroxylenol does not absorb at wavelengths >290 nm(3) and has been reported to be stable to sunlight for up to 24 hours(4).

An estimated BCF of 66 was calculated for chloroxylenol(SRC), using a log Kow of 3.27(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC), provided the compound is not metabolized by the organism(SRC).

The Koc of chloroxylenol is estimated as 1,400(SRC), using a log Kow of 3.27(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that chloroxylenol is expected to have low mobility in soil.

The Henry's Law constant for chloroxylenol is estimated as 5.1X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that chloroxylenol is expected to be essentially nonvolatile from moist soil and water surfaces(2). Chloroxylenol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.8X10-3 mm Hg(SRC), determined from a fragment constant method(3).

SURFACE WATER: Chloroxylenol was detected in 3 out of 10 estuaries in the United Kingdom in concentrations ranging from 581 to 4 ug/L(1).

Occupational exposure to chloroxylenol may occur through inhalation and dermal contact with this compound at workplaces where chloroxylenol is produced or used(SRC). The most likely route of exposure to the general population is through dermal contact when using soaps or cleaning products that contain chloroxylenol as an antibacterial(SRC). A smaller population may be exposed to chloroxylenol when taking medications that contain chloroxylenol as an active ingredient(1).

The predominant medical applications for which chloroxylenol is formally indicated for therapeutic use is as an application to the skin for use in cuts, bites, stings, abrasions, and for use as antiseptic hand cleaner.

Antibacterial; antiseptic (topical and urinary).|(VET): Antiseptic (topical).

Chloroxylenol is a substituted phenol which has been widely used for many years as an ingredient of antiseptic and disinfectant products intended for external use. It is known to be bactericidal in low concentration to a wide range of Gram positive and Gram negative bacteria.

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)|Agents that act systemically to kill adult schistosomes. (See all compounds classified as Schistosomicides.)|Substances used on inanimate objects that destroy harmful microorganisms or inhibit their activity. Disinfectants are classed as complete, destroying SPORES as well as vegetative forms of microorganisms, or incomplete, destroying only vegetative forms of the organisms. They are distinguished from ANTISEPTICS, which are local anti-infective agents used on humans and other animals. (From Hawley's Condensed Chemical Dictionary, 11th ed) (See all compounds classified as Disinfectants.)

No chloroxylenol was detected in the blood following the dermal administration of 2 g of p-chloroxylenol in an ethanol/olive oil vehicle in human subjects. After a dose of 5 g, only traces were found, after 8 g, 1 mg % (1 mg/dL) was found in the blood after 3 hours, and 4 mg % (4 mg/dL) after 24 hours. After a dose of 20 g, 4 mg % (4 mg/dL) was measured after half an hour, and 1 mg % (1 mg/dL) was present at 72 hours. For antiseptic purposes, chloroxylenol is considered to be well-absorbed when applied to the skin.|The major route of excretion is likely in urine, although some amounts may be found in bile and traces in exhaled air.|The only data available regarding the volume of distribution of chloroxylenol is the mean Vss of 22.45 L determined after 200 mg intravenous single dose of chloroxylenol was administered to healthy mongrel dog subjects.|The only data available regarding the clearance of chloroxylenol is the mean clearance rate of 13.76 L/hr following a 200 mg intravenous single dose of the substance into healthy mongrel dog subjects. Moreover, in another study, when 8 g of chloroxylenol was administered dermal on a human subject in an alcohol/glycerin vehicle, 11% was excreted in 48 hours.|Mongrel dogs received iv and oral single doses of 200 and 2000 mg 4-chloro-3,5-xylenol, respectively. Low range of absorption was noted. Kidneys were not the major route for rapid elimination of unchanged 4-chloro-3,5-xylenol.|Tests of a 25 percent solution of chloroxylenol with Sprague-Dawley rats demonstrated the chemical was practically all eliminated in the first 24 hours, mostly in the urine, with small amounts in feces, after oral or dermal exposure. Following dermal exposure, about half of the material was not absorbed. High concentrations were found in the tissues of the kidney, which indicates excretion in urine. Concentrations in the lungs indicates some elimination in expired air.|In a study /with/ beagle dogs dosed orally excreted virtually all of the chloroxylenol in their urine within 24 hours. A small amount was present in feces, but essentially none remained in any tissue.|The pharmacokinetic and metabolic profile of p-chloro-m-xylenol (PCMX) was studied in healthy mongrel dogs after intravenous and oral administration of single doses of 200 and 2000 mg of PCMX, respectively. ... The mean half-life and mean residence time were 1.84 and 1.69 hr. respectively. The apparent volume of distribution at steady state was estimated to be 22.4 liters, and the plasma clearance was 14.6 liters/hr. The bioavailability of PCMX was 21%. ... PCMX's metabolite data show that a presystemic elimination process (first-pass effect) is also occurring. PCMX plasma concentrations after intravenous administration of 500-, 200-, and 100-mg doses were found to be proportional to the dose given.

Certain animal studies have shown that following dermal application of chloroxylenol, that the absorption was rapid with a Cmax = 1-2 hours, and that the administered substance was excreted via the kidney with almost complete elimination within 24 hours. The primary metabolites discovered in the excreted urine were glucuronides and sulfates. Some chloroxylenol monographs liken its pharmacokinetic profile to that of another antiseptic - triclosan - which is rapidly excreted in the urine also as a glucuronide metabolite, as observed in the human model. Moreover, In one human subject administered 5 mg intragluteally, 14% was excreted with glucuronic acid and 17% with sulfuric acid at 3 days. Any chloroxylenol absorbed into the body is likely extensively metabolized by the liver and rapidly excreted, mainly in the urine, as sulphate and glucuronide conjugates.|Mongrel dogs received iv and oral single doses of 200 and 2000 mg 4-chloro-3,5-xylenol, respectively. ...Main metabolites found in the urine were glucuronides and sulfates.

One study estimated the mean terminal half-life and mean residence time after a 200 mg intravenous single dose of chloroxylenol in healthy mongrel dog subjects to be 1.7 and 1.69 hours, respectively. Alternatively, some product monographs liken chloroxylenol to a similar liquid antiseptic, triclosan, whose calculated urinary excretion half-life in man is approximately 10 hours.

As a phenol antiseptic, it is believed that the hydroxyl -OH groups of the chloroxylenol molecule binds to certain proteins on the cell membrane of bacteria, and disrupts the membrane so as to allow the contents of the bacterial cell to leak out. This allows chloroxylenol to enter the bacterial cell to bind further with more proteins and enzymes to disable the cell's functioning. At particularly high concentrations of chloroxylenol, the protein and nucleic acid content of targeted bacterial cells become coagulated and cease to function, leading to rapid cell death.

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Administer activated charcoal ... . Do not use emetics. Cover skin burns with dry, sterile dressings after decontamination ... . Maintain body temperature. /Phenols and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors for hypotension with a normal fluid volume. Watch for signs of fluid overload ... Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Treat seizures with diazepam (Valium). ... Use proparacaine hydrochloride to assist eye irrigation ... . /Phenols and related compounds/

/HUMAN EXPOSURE STUDIES/ Contact dermatitis was found in workers occupationally exposed to 4-chloro-3,5-xylenol.|/CASE REPORTS/ Incidences of occupational allergic contact dermatitis caused by exposure to parachlorometaxylenol (PCMX) were examined.|/OTHER TOXICITY INFORMATION/ Chloroxylenol /is listed as one of/ common contact allergens /in/ antiseptics. /from Table/

2-chloro-5-hydroxy-1,3-dimethylbenzene

Dettol (Reckitt and Colman, UK)

Soap, cleaning compound, and toilet preparation manufacturing|Phenol, 4-chloro-3,5-dimethyl-: ACTIVE|Claimed to be about 60 times as potent as phenol.

Cosmetics -> Preservative