Chlorophene
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Chlorophene
structure -
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CAS No:
120-32-1
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Formula:
C13H11ClO
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Chemical Name:
Chlorophene
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Synonyms:
Phenol,4-chloro-2-(phenylmethyl)-;o-Cresol,4-chloro-α-phenyl-;4-Chloro-2-(phenylmethyl)phenol;2-Benzyl-4-chlorophenol;5-Chloro-2-hydroxydiphenylmethane;4-Chloro-α-phenyl-o-cresol;Clorofene;Clorophene;Santophen 1;Santophen;Ketolin H;Neosabenyl;o-Benzyl-p-chlorophenol;4-Chloro-2-benzylphenol;Chlorophene;Bio-Clave;Septiphene;p-Chloro-o-benzylphenol;2-Hydroxy-5-chlorodiphenylmethane;Preventol BP;Nipacide BCP;NSC 59989;Nipacide BCP 50;Septol;8013-49-8;144246-47-9
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CAS No:
Description
SolidWhite to light tan or pink flakes or white crystals. Insoluble in water. Slight phenolic odor.
Ortho-benzyl-para-chlorophenol appears as white to light tan or pink flakes or white crystals. Insoluble in water. Slight phenolic odor. (NTP, 1992)
Ortho-benzyl-para-chlorophenol appears as white to light tan or pink flakes or white crystals. Insoluble in water. Slight phenolic odor. (NTP, 1992)
Chlorophene Basic Attributes
218.68
218.68
1959194
204-385-8
7560BB0BO3
59989
3077
DTXSID5020154
White to light tan or pink flakes
29081000
Characteristics
20.2
4
Ortho-benzyl-para-chlorophenol appears as white to light tan or pink flakes or white crystals. Insoluble in water. Slight phenolic odor. (NTP, 1992)
1.185 at 58 deg C
48.5 °C
160-162 °C @ Press: 3.5 Torr
>230 °F
1.5260 (estimate)
H2O: <0.1 g/100 mL at 16 ºC
Store below +30°C.
1.87X10-7 kPa = 1.4X10-6 mm Hg /extrapolated/
Oral-rat LD50: 1700 mg/kg; Oral-Mouse LD50: 65 mg/kg
Flammable; burning produces toxic chloride fumes
White to light tan or pink flakes
Henry's Law constant = 2.7X10-9 atm-cu m/mole at 25 °C (est)
Crystallizing point 45 °C min; dispersible in aqueous media with aid of soaps or synthetic dispersing agents|Hydroxyl radical reaction rate constant = 1.8X10-11 cu cm/molec-sec at 25 °C (est)
Insoluble in water.
Phenols and Cresols
ORTHO-BENZYL-PARA-CHLOROPHENOL is incompatible with acids and oxidizing agents (NTP, 1992). Is sensitive to light. Stable at temperatures up to 77°F when protected from light, but storage at 140° F causes decomposition.
Noncorrosive to most metals
Safety Information
III
9
UN 3077 9/PG 3
2
22-37/38-41-50/53-51/53-36/37/38
26-39-60-61-37/39
GO7175000
Xn,N
Ventilated, low temperature and dry; stored separately from food materials in warehouse
Stable.
P261-P273-P280-P305 + P351 + P338-P501
H302-H315-H318-H335-H410
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.
DHHS/NTP; Toxicology & Carcinogenesis Studies of o-Benzyl-p-chlorophenol in F344/N Rats and B6C3F1 Mice (Gavage Studies) Technical Report Series No. 424 (1994) NIH Publication No. 94-3155|USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - ortho-benzyl-para-chlorophenol. 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 6, 2006: http://www.epa.gov/pesticides/reregistration/status.htm]
This chemical is combustible. (NTP, 1992)
|Danger|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P260, P261, P264, P271, P272, P273, P280, P281, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P321, P332+P313, P333+P313, P362, P363, P391, P405, and P501|H302 (35.23%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P272, P273, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P321, P330, P332+P313, P333+P313, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 181 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P261, P264, P271, P272, P273, P280, P281, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P332+P313, P333+P313, P362, P363, P391, P405, and P501|P201, P202, P260, P261, P264, P270, P271, P272, P273, P280, P281, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P309+P311, P310, P312, P314, P321, P332+P313, P333+P313, P362, P363, P391, P405, and P501
Fires involving this compound should be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this chemical under refrigerated temperatures, and protect it from light. (NTP, 1992)
MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Combustible
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.|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
In formulations of 10% or more, it is a primary skin irritant. ... Only mild skin irritation after prolonged contact with use dilutions (0.03%).
Influent and effluent samples from 11 municipal sewage treatment plants in St. Louis, MO and Dayton, OH, were obtained during November, 1978 and August, 1981 respectively. Influent concentrations averaged 14.8 ug/L o-benzyl-p-chlorophenol with a range of concentrations from <0.1 to 115 ug/L. Effluent concentrations averaged 0.8 ug/L o-benzyl-p-chlorophenol with a range of concentrations from <0.1 to 28 ug/L. Sludge concentrations were an average of 23 mg/kg o-benzyl-p-chlorophenol with a range of concentrations from 13 to 30 mg/kg(1). Municipal wastewater was monitored in Vancouver, BC from June through August 1983; o-benzyl-p-chlorophenol was qualitatively detected in both wastewater and sludge base/neutral extracts(2). o-Benzyl-p-chlorophenol was identified, not quantified, in the effluent of a sewage treatment plant in New Jersey at an unreported date; there were no industrial contributors to this waste site(3).
Toxicity
highly toxic
LD50 Rat oral 1700 mg/kg|LD50 Mouse oral 65 mg/kg|LD50 Mouse sc 350 mg/kg
Groups of 80 male and 80 female F344/N rats were administered o-benzyl-p-chlorophenol in corn oil by gavage 5 days/wk for 103 wk. The doses were 0, 30, 60 or 120 mg/kg body weight for male rats and 0, 60, 120 or 240 mg/kg body weight for female rats. ... Under the conditions of these 2 yr gavage studies, there was no evidence of carcinogenic activity of o-benzyl-p-chlorophenol in male F344/N rats receiving 30, 60 or 120 mg/kg body weight. There was equivocal evidence of carcinogenic activity of o-benzyl-p-chlorophenol in female F344/N rats based on the occurrence of two rare renal transitional cell carcinomas. Groups of 70 male and 70 female B6C3F1 mice were administered o-benzyl-p-chlorophenol in corn oil by gavage at doses of 0, 120, 240 or 480 mg/kg body weight 5 days/wk for 103 wk. There was some evidence of carcinogenic activity of o-benzyl-p-chlorophenol in male B6C3F1 mice based on increased incidence of renal tubule adenoma and renal tubule adenoma or carcinoma (combined). There was no evidence of carcinogenic activity of o-benzyl-p-chlorophenol in female B6C3F1 mice receiving 120, 240 or 480 mg/kg body weight.|Groups of 50 male and 50 female Swiss CD-1 mice were topically exposed to o-benzyl-p-chlorophenol (BCP) to study its effect as an initiator, promoter, and complete carcinogen. A number of control groups were included in these studies as a reference for the responses of the mouse skin to (BCP). ... Results in the Study of BCP as a Complete Carcinogen: BCP acted as an irritant when tested as a complete carcinogen using a single initiating dose of 10 mg BCP followed by repetitive applications of 0.1, 1.0, or 3.0 mg BCP for up to 52 wk, and many mice developed cutaneous lesions of scaling/crusts and ulceration. During the course of the study, a single papilloma was first observed after 12 wk in one 0.1 mg BCP male mouse. One 3.0 mg BCP female was observed with a papilloma at week 10, and three 0.1 mg BCP females were observed with papillomas between weeks 22 and 27. No mice administered BCP/BCP had papillomas at the end of the study, and no malignant cutaneous epithelial tumors were observed at the application sites on any BCP/BCP treated mice. Thus, in the present study, BCP was not a complete carcinogen.|Groups of 50 male and 50 female Swiss CD-1 mice were topically exposed to o-benzyl-p-chlorophenol (BCP) to study its effect as an initiator, promoter, and complete carcinogen. A number of control groups were included in these studies as a reference for the responses of the mouse skin to (BCP). ... Results in the Study of BCP as an Initiator: One vehicle control (acetone/acetone) male mouse had developed crusts at the site of application at necropsy, but no male or female controls had developed papillomas. Mice administered BCP/TPA developed application site lesions including scaling/crusts, ulceration, and irritation; the incidences of these lesions were similar to those in the initiator/promoter control (DMBA/TPA) groups. After 22 wk papillomas were observed in 12/50 male mice administered BCP/TPA. After 12 wk papillomas were observed in 7/50 female mice administered BCP/TPA. However, the incidences of papillomas in mice administered BCP/TPA were lower than those in mice administered TPA/TPA (males, 40/50; females 48/50). Although the incidences of papillomas in mice administered BCP as an initiator were significantly greater than those in vehicle controls, the incidences were not significantly different from those in TPA/TPA mice. Thus, in the present study, BCP did not demonstrate initiating potential.|Groups of 50 male and 50 female Swiss CD-1 mice were topically exposed to o-benzyl-p-chlorophenol (BCP) to study its effect as an initiator, promoter, and complete carcinogen. A number of control groups were included in these studies as a reference for the responses of the mouse skin to (BCP). ... Results in the Study of BCP as a Promoter: During the course of the study, incidences of scaling and/or crusts, ulceration, and irritation were observed at the site of application in DMBA/BCP male and female mice, and the incidences were dose related. Incidences of scaling and/or crusts, ulceration, and irritation in 3.0 mg BCP mice were similar to the incidences of these lesions in initiator/promoter (DMBA/TPA) group, but much higher than the incidences of these lesions in the initiator control (DMBA/acetone) group. A dose-related increased incidence of papillomas was observed in males (DMBA/acetone, 8/50; DMBA/0.1 mg BCP, 3/50; DMBA/1.0 mg BCP, 5/50; and DMBA/3.0 mg BCP, 14/50) and females (2/50, 6/50, 6/50, 18/50). The incidence of papillomas in DMBA/3.0 mg BCP females was significantly greater (p<0.001) than that in DMBA/acetone females; the incidence of papillomas in DMBA/3.0 mg BCP males was marginally increased (p=0.077). No acetone/acetone mice developed papillomas. Although a higher percentage of DMBA/3.0 mg BCP mice developed papillomas over the course of the study than did DMBA/acetone controls, the time it took for half of the number of responding animals to develop papillomas was similar between DMBA/acetone groups and DMBA/3.0 mg BCP groups (DMBA/acetone males, wk 38; DMBA/acetone females, wk 34; DMBA/3.0 mg BCP females, wk 37). However, the time to appearance of the first papilloma was shorter in DMBA/3.0 mg BCP mice (males, wk 18; females, 10) than DMBA/acetone mice (males, wk 26; females, wk 27). BCP was considered to have promotion potential because the incidences of papillomas were greater than those in DMBA/acetone (initiator control) mice and because topical exposure to BCP alone caused no significant incr incidences of papillomas. However, the incidences of papillomas in DMBA/3.0 mg BCP mice (males, 14/50; females, 18/50) were much less than the incidences in DMBA/TPA (promoter control) mice (males, 40/50; females, 48/50); thus BCP was classified as a weak promoter. Conclusions: Under the conditions of this 1 yr mouse skin initiation/promotion study in swiss (CD-1) mice, o-benzyl-p-chlorophenol was a cutaneous irritant and a weak skin tumor promoter relative to strong promoters such as TPA. BCP had no activity as an initiator or as a complete carcinogen.
o-Benzyl-p-chlorophenol's production may result in its release to the environment through various waste streams; it's use as a disinfectant and broad spectrum germicide(1) will result in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 2,050(2), indicates that o-benzyl-p-chlorophenol is expected to have slight mobility in soil(SRC). Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 2.7X10-9 atm-cu m/mole(SRC) derived from its extrapolated vapor pressure, 1.4X10-6 mm Hg(2), and water solubility, 149 mg/L(2). Volatilization from dry soil surfaces is not expected to be important based on the vapor pressure of this compound(2). Biodegradation of o-benzyl-p-chlorophenol is expected to occur rapidly based on degradation half-lives of 1 to 2 days, in a sewage sludge(2).|AQUATIC FATE: Based on a classification scheme(1), a Koc value of 2,050 (2), indicates that o-benzyl-p-chlorophenol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected to be an important fate process(3) based upon an estimated Henry's Law constant of 2.7X10-9 atm-cu m/mole(SRC) derived from its extrapolated vapor pressure, 1.4X10-6 mm Hg(2), and water solubility, 149 mg/L(2). According to a classification scheme(4), a BCF of 75 measured in fish(2), suggests bioconcentration in aquatic organisms is moderate(SRC). An aqueous photolysis half-life of approximately 0.7 days(2), indicates photolysis in sunlit surface waters will be an important fate process(SRC). In addition, river die-away studies using non-acclimated river water indicates that the biodegradation half-life of o-benzyl-p-chlorophenol is approximately 1 to 3 days(2,5).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), o-benzyl-p-chlorophenol, which has an extrapolated vapor pressure of 1.4X10-6 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase o-benzyl-p-chlorophenol 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 about 22 hours (SRC), calculated from its rate constant of 1.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase o-benzyl-p-chlorophenol may be removed from the air by wet and dry deposition(SRC). o-Benzyl-p-chlorophenol has been shown to undergo direct photolysis in aqueous solutions with a half-life of approximately 0.7 days(2), which indicates that direct photolysis in the atmosphere may be possible(SRC).
The rate constant for the vapor-phase reaction of o-benzyl-p-chlorophenol with photochemically produced hydroxyl radicals is estimated as 1.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 22 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1). Rates of hydrolysis for o-benzyl-p-chlorophenol were calculated for pH values of 5, 7, and 9 and at both 25 and 50 °C. For these conditions the rate constant for hydrolysis was <0.005/days(1); therefore hydrolysis of this compound is not expected to occur in the environment(2). Photolysis of o-benzyl-p-chlorophenol in natural water was measured in quartz tubes exposed to sunlight, yielding a rate constant of 0.95/days with a corresponding half life of 0.7 days(2).
A BCF value of 75 was measured for bluegill sunfish(1). Bluegill sunfish (Lepomis machrochirus) were exposed to 0.057 mg/L o-benzyl-p-chlorophenol for a period of 96 hours followed by a depuration period of 96 hours to determine the ability of the fish to metabolize and eliminate o-benzyl-p-chlorophenol. Depuration rate constants were from 4.67 to 6.94/days with a half-life of 0.14 days(1). The rate constant of o-benzyl-p-chlorophenol uptake in fish ranged from 11.8 to 13.8/days with a half-life of 0.06 days. According to a classification scheme(2), this BCF value suggests that bioconcentration in aquatic organisms is moderate(SRC).
An experimentally determined Koc of 2050 was obtained by equilibrating aqueous solutions of o-benzyl-p-chlorophenol (at concentrations ranging from 0.5 to 10 mg/L) with four different soils, with organic carbon contents ranging from 0.41 to 1.97%, and then analyzing both soil and water phases for o-benzyl-p-chlorophenol(1). According to a suggested classification scheme(2), this Koc value indicates that o-benzyl-p-chlorophenol is expected to have slight mobility in soil(SRC).
The Henry's Law constant for o-benzyl-p-chlorophenol is estimated as 2.7X10-9 atm-cu m/mole(SRC) derived from its extrapolated vapor pressure, 1.4X10-6 mm Hg(1), and water solubility, 149 mg/L(1). This Henry's Law constant indicates that o-benzyl-p-chlorophenol is expected to be essentially non-volatile from water and moist soil surfaces(2). o-Benzyl-p-chlorophenol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
SURFACE WATER: o-Benzyl-p-chlorophenol was detected in surface waters in the United States (18 sites, 54 samples, 2 positive samples, mean positive = 16.5 ug/L, geometric mean concentration = <0.11 ug/L, detection limit = 0.11 ug/L)(1). Only two samples had measurable concentrations of o-benzyl-p-chlorophenol, the Illinois River, 0.12 ug/L, and the Delaware Bay, 0.21 ug/L.
NIOSH (NOES Survey 1981-1983) has statistically estimated that 347,634 workers (244,212 of these are female) are potentially exposed to o-benzyl-p-chlorophenol in the US(1). Occupational exposure to o-benzyl-p-chlorophenol may occur through dermal contact with this compound at workplaces where it is produced or used(SRC). The general population may be exposed to o-benzyl-p-chlorophenol through dermal exposure when using this compound as a household disinfectant(SRC).
Drug Information
3. 3= MODERATELY TOXIC:Probable oral lethal dose (human) 0.5-5 g/kg, between 1 oz and 1 pint for 70 kg person (150 lbs).
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.)
Chlorophene was applied to the intrascapular region of male Fischer-344 rats at a total dose of 10 mg/kg in dermal studies. Three days after exposure to Chlorophene, 59% of the dose was excreted in the urine and feces. Chlorophene was distributed, as a percent of the total dose, to large intestinal contents (1.58%), small intestinal contents (0.55%), the skin (0.23%), and the skin site (32.33%). Chlorophene was incompletely absorbed through the skin.|Rats /were/ dosed with 10 mg/kg chlorophene /iv/ and three rats each were sacrificed at various time points from 15 min to 72 hr. After iv exposure, 88% of the dose was excreted by 72 hr. After 15 min of treatment, about 30% of the chlorophene dose administered was present in the intestinal contents. Radioactivity was greatest in the kidneys and liver at this same time point and remained the greatest after 72 hr. The relative percent of unmetabolized chlorophene increased with time in the blood and liver over 72 hr. However, in the kidneys, it decreased with time. The skin had significant chlorophene radioactivity, 7.92% of the total dose administered after 15 min, but little remained after 24 hr.|/Investigators/ dosed rats orally with 10, 100, or 1000 mg/kg chlorophene. The relative concentration of chlorophene excreted in the urine and feces was dose dependent. At the low and high dose, feces were the major route of excretion, whereas at the intermediate dose, urinary excretion predominated. However, more than 92% of the radioactive chlorophene was excreted within 3 days by rats in all dose groups. Rats injected with 5, 10, or 25 mg/kg chlorophene in the femoral vein had a dose-related decrease in biliary excretion.|Male Sprague-Dawley rats /were administered/ (3/dose level) a single dose of 69 or 206 mg/kg [14C]-chlorophene. The kidneys and liver had the highest radiochemical concentrations of chlorophene and its metabolites. The combined concentrations of these two organs accounted for 0.16% and 0.13% of the 69 and 206 mg/kg doses, respectively. Approximately 0.23% and 0.18% of the dose was associated with the body fat at the low and high dose, respectively.|For more Absorption, Distribution and Excretion (Complete) data for O-BENZYL-P-CHLOROPHENOL (8 total), please visit the HSDB record page.
After iv treatment with 10 mg/kg chlorophene, the major metabolite formed was the glucuronic acid conjugate of the parent compound. The metabolite gradually decreased over a 6-hr period after treatment. The oxidative metabolite increased from 0.5% to 6% of the glucuronide acid conjugates in bile over 6 hr.|In vitro metabolism studies found that about 95% of chlorophene was metabolized by liver supernatant in the presence of NADPH, uridine diphosphoglucuronic acid (UDPGA), and glutathione (GSH). Metabolism varied from 14% to 51% as the parent compound was exposed to various combinations of the cofactors, microsomes, and organ extracts.|/Investigators/ isolated the metabolites of [14C]-chlorophene in urine and feces over a 5-day period. A significant percentage of the radioactive dose was present in the urine and feces from 12 to 24 hr. The majority of metabolites were present as either glucuronide or sulfate ester conjugates in the urine during this time period. Two additional metabolites were also identified, one in which the benzyl aromatic ring had a hydroxyl and a methoxyl substituent (22.9% and 17.6% of the low and high dose, respectively) and the second in which the benzyl aromatic ring had a hydroxyl substituent (12.7% and 29.4% of the low and high dose, respectively). These same metabolites were identified in feces but at a lower concentration. Chlorophene was also identified in the urine as 5.3% and 14.1% of the low and high dose, respectively. However, a larger percentage of [14C]-chlorophene was identified in feces, 21.4% and 22.4% of the low and high dose, respectively.|Undiluted chlorophene (2 mL/kg) applied to the skin of rabbits lowered the percent of inorganic sulfates. However, the amount of glucuronate excreted was not affected. Application of 0.2 g/kg chlorophene in cottonseed oil and castor oil soap caused a slight increase in the output of glucuronates, but did not affect excretion of sulfates. The dilutions (1:100 and 1:300) produced no change in the excretion of glucuronates or sulfates.|For more Metabolism/Metabolites (Complete) data for O-BENZYL-P-CHLOROPHENOL (7 total), please visit the HSDB record page.
Male rats given an oral dose of 69 mg/kg or 206 mg/kg (14)C labeled o-benzyl-p-chlorophenol. ... Excretion of o-benzyl-p-chlorophenol was biphasic with an initial rapid alpha phase with a half life of 8 to 9 hr and slightly slower beta phase estimated to have a half life of 52 to 140 hr. ...|After iv injections of 10 mg/kg, ... feces, or feces and urine combined /were collected/, /investigators/ describe the elimination phase as a single-component model with a half-life of 14 hr.
SYMPTOMS: Symptoms of exposure to this compound in humans include drowsiness, loss of consciousness, irregular pulse and cyanosis. It may also cause irritation of the skin and mucous membranes. It is corrosive to the eyes, and extremely corrosive to the mouth and throat. Swallowing dusts or solids causes severe and rapid burning of the mouth, throat and digestive tract accompanied by severe pain, vomiting and collapse. It has also caused severe porphyrea cutanea tarda. ACUTE/CHRONIC HAZARDS: This compound is a highly toxic irritant. It is irritating to the skin and respiratory tract, and corrosive to the eyes. It is also extremely corrosive to the mouth and throat. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide, chlorine or hydrogen chloride, and other unidentified organic compounds in black smoke. (NTP, 1992)
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Phenols are very toxic poisons AND corrosive and irritating, so that inducing vomiting may make medical problems worse. IMMEDIATELY call a hospital or poison control center and locate activated charcoal, egg whites, or milk in case the medical advisor recommends administering one of them. If advice from a physician is not readily available and the victim is conscious and not convulsing, give the victim a glass of activated charcoal slurry in water or, if this is not available, a glass of milk, or beaten egg whites and IMMEDIATELY transport victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, assure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
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/ /Investigators/ studied two epidemics of hyperbilirubinemia in infants in two hospitals. A total of 10 infants were diagnosed with hyperbilirubinemia between the two hospitals. The infants were exposed to a germicidal phenolic compound that contained 3.5% chlorophene and other ingredients. Serum samples were analyzed for chlorophene and 7/10 infants from the same hospital had positive results that ranged from 360 to 4390 ng/mL.|/SIGNS AND SYMPTOMS/ SYMPTOMATOLOGY: 1. Burning pain in mouth & throat. White necrotic lesions in mouth, esophagus & stomach. Abdominal pain, vomiting...& bloody diarrhea. 2. Pallor, sweating, weakness, headache, dizziness, tinnitus. 3. Shock: weak irregular pulse, hypotension, shallow respirations, cyanosis, and a profound fall in body temperature. 4. Possibly fleeting excitement (delirium), followed by unconsciousness. Convulsions are rarely seen except in children. 5. Stertorous breathing, mucous rales, rhonchi, frothing at nose & mouth ... pulmonary edema are sometimes seen. Characteristic odor of phenol on breath. Scanty, dark-colored or "smoky" urine. 6. If death does not occur promptly, moderately severe renal insufficiency may appear. 7. Death from respiratory, circulatory or cardiac failure. 8. If spilled on skin, pain is followed promptly by numbness. The skin becomes blanched, & a dry opaque eschar forms over the burn. When the eschar sloughs off, a brown stain remains. /Phenol/|/CASE REPORTS/ A cleaning woman who mixed a commercial solution of this disinfectant with hypochlorite bleach suffered a severe attack of porphyrea cutanea tarda, probably because of polychlorinated phenolic derivatives generated in the mixture ... .|/CASE REPORTS/ A 49-year-old subject presented with a 1-year history of an itchy, erythematous, scaly eruption that involved the fingers, finger webs, palms, dorsa of both hands, and patches on the right forearm. Subsequent patch testing with a 1% chlorophene concentration produced a strong positive reaction (++). Control subjects (50) were also patch tested with a 1% chlorophene concentration, of which 3 subjects had mild irritant reactions and 47 had no reaction.|For more Human Toxicity Excerpts (Complete) data for O-BENZYL-P-CHLOROPHENOL (9 total), please visit the HSDB record page.
2-benzyl-4-chlorophenol
Chlorophene Use and Manufacturing
General procedure: In each case, o-, m- or p-chlorophenol(0.2 g, 1.56 mmol) was added to benzyl bromide (0.19 mL, 1.60 mmol, 1 equiv)under argon. ZnCl2(anhyd.) (0.045 g, 0.33 mmol, 0.2 equiv) was addedand the reaction stirred at 60°C for 2 hours after which heating was increasedto 90°C after which heating was halted and the reaction was allowed to cool toRT and the reaction was quenched with H2O (15 mL). The reactionmixture was extracted with ether (15 mL) that was then washed with 2 M HCl (15mL) and H2O (15 mL). The ether layer was extracted with KOH(aq)(0.1 M, 3 x 15 mL), the alkaline layer was washed with ether (20 mL) and theaqueous phase acidified with HCl (2 M). Finally, the aqueous phase wasextracted with ether (2 x 20 mL) that was dried with MgSO4 andpurified in each case using silica gel to yield the relevant mono- ordi-alkylated chlorophenol. From reaction with para-chlorophenol, 2-benzyl-4-chlorophenol (1, 0.002 g, 0.6percent yield) and 2, 6-dibenzyl-4-chlorophenol (2, 0.006 g, 1.2percent yield) were isolated.2-Benzyl-4-chlorophenol (1): All spectroscopic data identical tonatural product.2, 6-Dibenzyl-4-chlorophenol (2): white amorphous solid; HRESIMS:[M-H]- m/z obs: 307.0857, calcd for C20H17OCl: 307.8095 (Δ -3.8 mmu); 13CNMR (150 MHz, CDCl3): δC 150.9 (C-1), 138.9 (C-1”), 129.1(C-2), 129.0 (C-3”), 128.9 (C-3), 128.8 (C-2”), 126.9 (C-4”), 125.4 (C-4), 36.6(C-1’); 1H NMR (600 MHz, CDCl3): δH 7.31 (t, 7.5 Hz, 4H, H-3”), 7.24 (t, 7.4 Hz, 2H, H-4”), 7.20 (d, 7.6 Hz, 4H, H-2”), 7.00(s, 2H, H-3), 4.60 (s, 1H, OH-1), 3.93 (s, 4H, H-1’).
In household, hospital and veterinary disinfectant preparations.
(1977) PROBABLY GREATER THAN 2.27X10+6 GRAMS|(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS|Annual production averages less than 4.5X10+6 kg.|(1986) 10 thousand-500 thousand pounds|For more U.S. Production (Complete) data for O-BENZYL-P-CHLOROPHENOL (7 total), please visit the HSDB record page.
Phenol, 4-chloro-2-(phenylmethyl)-: ACTIVE
Thin-layer chromatography on silica gel 60 F254 with PHME-MECO2 (4:1) or ethyl acetate-methanol-10% ammonium hydroxide (65:30:5) was used to separate 38 preservatives used in cosmetics. The compounds were identified by color reactions with 12 spray reagent systems.|Mixture of 22 bactericides were separated by programmed-temp gas chromatography between 100 & 300 °C using columns with 10% silicone rubber W-982 on Chromosorb W (DMCS, 60-80 MESH) as stationary phase & flame ionization detector.
Determination of 3 germicidal phenols in serum of infants with hyperbilirubinemia by HPLC. Chlorophene was among germicidal agents determined by high pressure liquid chromatography.
Agrochemicals -> Fungicides|Cosmetics -> Preservative
Computed Properties
Molecular Weight:218.68
XLogP3:4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:218.0498427
Monoisotopic Mass:218.0498427
Topological Polar Surface Area:20.2
Heavy Atom Count:15
Complexity:189
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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