4-Chloro-2-methylphenol
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4-Chloro-2-methylphenol
structure -
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CAS No:
1570-64-5
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Formula:
C7H7ClO
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Chemical Name:
4-Chloro-2-methylphenol
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Synonyms:
Phenol,4-chloro-2-methyl-;o-Cresol,4-chloro-;4-Chloro-2-methylphenol;4-Chloro-o-cresol;p-Chloro-o-cresol;4-Chloro-2-cresol;5-Chloro-2-hydroxytoluene;PCOC;NSC 2851;4-Chlorocresol
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CAS No:
Description
Off-white to slightly brownish crystalline solidChEBI: A member of the class of phenols that is o-cresol in which the hydrogen para to the hydroxy group is replaced by a chlorine.Dark red flakes with waxy texture. Insoluble in water.
P-chloro-o-cresol is a dark red flakes with waxy texture. Insoluble in water.|CRYSTALS.
P-chloro-o-cresol is a dark red flakes with waxy texture. Insoluble in water.|4-chloro-2-methylphenol is a member of the class of phenols that is o-cresol in which the hydrogen para to the hydroxy group is replaced by a chlorine. It is a member of phenols and a member of monochlorobenzenes. It derives from an o-cresol.
4-Chloro-2-methylphenol Basic Attributes
142.58
142.58
216-381-3
297V63W9RI
1476
2851
2669
DTXSID5022510
Needles from petroleum ether|Pale yellow solid
29081990
Characteristics
20.2
2.8
P-chloro-o-cresol is a dark red flakes with waxy texture. Insoluble in water.
1.2 g/cm3
51 °C
223 °C
>230 °F
1.5449 (estimate)
<0.1 g/100 mL at 15 ºCInsoluble in water.
0-6ºC
2.40X10-2 mm Hg @ 25 deg C
Mild, phenolic odor
Henry's Law constant = 1.1X10-6 atm-cu m/mol @ 25 °C
pKa = 9.71
Insoluble in water.
Phenols and Cresols
P-CHLORO-O-CRESOL can react vigorously with concentrated sodium hydroxide solutions. Also reacts with other bases, acid chlorides, acid anhydrides, and oxidizing agents. Corrodes steel, brass, copper and copper alloys [NTP, 1992)]. A large quantity left in contact with concentrated sodium hydroxide solution for 3 days reacted violently, attaining red heat and evolving fumes that ignited explosively. The heat of reaction dissipated poorly because of the high viscosity of the mixture [Quart. Safety Summ., 1957, 28, 39].
Safety Information
II
6.1
UN 3437 6.1/PG 2
2
R23;R35;R50
26-36/37/39-45-61-28
GO7120000
T,C,N,Xn
Stable under normal temperatures and pressures.
P261-P280-P303 + P361 + P353-P304 + P340 + P310-P305 + P351 + P338-P403 + P233
H314-H331-H400
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|The environmentally hazardous organic substances /including 4-chloro-2-methylphenol/ in the waste water from the manufacture of chlorophenoxyalkanoic acids were identified and semiquantified before & after passing through a biological treatment plant for municipal sewage, the secondary effluent of which was discharged into a marine ecosystem. The removal of chlorophenols was good, with a 90% overall reduction of chlorinated substances in the sewage passing through the treatment plant.
A large quantitiy (700 kg) of /4-chloro-2-methylphenol/, left in contact with concentrated sodium hydroxide soln for 3 days, decomposed, attaining red heat and evolving fumes which ignited explosively. Although this could not be reproduced under laboratory conditions, it is believed that exothermic hydrolysis to the hydroquinone (possibly with subsequent aerobic oxidation to the quinone) occurred, the high viscosity of the liquid preventing dissipation of heat.
USEPA; Ambient Water Quality Criteria Doc: Chlorinated Phenols (1980) EPA 440/5-80-032.|Nat'l Research Council Canada; Chlorinated Phenols (1982) NRCC No. 18578|BIBRA working group; TA: Toxicity profile. BIBRA Toxicology Intl: 7 (1992).|Gesellschaft Deutscher Chemiker (GDCh) - Advisory Committee on Existing Chemicals of Environmental Relevance (BUA). S. Hirzel Verlag, P.O. Box 10 10 61, 70009 Stuttgart, Germany (1995).
This chemical is probably combustible. (NTP, 1992)|Combustible.
|Danger|H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P261, P264, P271, P273, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P321, P363, P391, P403+P233, P405, and P501|H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|Aggregated GHS information provided by 85 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P260, P261, P264, P271, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P321, P363, P403+P233, P405, and P501
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)|Use water spray, foam, dry powder, carbon dioxide.
Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]: 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 keep it away from oxidizing materials. STORE AWAY FROM SOURCES OF IGNITION. (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)
Gamma-ray-induced degradation on nonbiodegradable organic compounds is demonstrated on chlorophenols and 4-chlorocresol. The oxidation in aqueous solutions with air at doses up to 1 Mrad results in complete dechlorination. The following organic compounds have been identified in the case of 4-chlorocresol as oxidation products: oxalic acid, formic acid (HCO2H), acetic acid (HOAC), glyoxal, mesoxalic acid, mesoxalic acid semialdehyde.|Activated carbon adsorption was used for spill cleanup in the manufacture of chlorinated pesticides, including 4-chloro-2-methylphenol.|Activated carbon is a good method for removing chlorophenols from water. Competitive adsorption occurs between chlorophenols and humic substances present in nearly all municipal water supplies. This competition decreases the capacity of carbon for chlorophenols. /Chlorophenols/
/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Health: 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. /Chlorocresols; Chlorocresols, liquid; Chlorocresols, solid; Chlorocresols, solution/|/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Fire or Explosion: 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. /Chlorocresols; Chlorocresols, liquid; Chlorocresols, solid; Chlorocresols, solution/|/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . 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. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. /Chlorocresols; Chlorocresols, liquid; Chlorocresols, solid; Chlorocresols, solution/|/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Chlorocresols; Chlorocresols, liquid; Chlorocresols, solid; Chlorocresols, solution/|For more DOT Emergency Guidelines (Complete) data for 4-CHLORO-2-METHYLPHENOL (8 total), please visit the HSDB record page.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
Consult an expert! Personal protection: chemical protection suit including self-contained breathing apparatus. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Do NOT let this chemical enter the environment.
No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
The substance is corrosive to the eyes, skin and respiratory tract. Inhalation may cause lung oedema. Corrosive on ingestion.
NO open flames.
AVOID ALL CONTACT!
Use ventilation, local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear face shield or eye protection in combination with breathing protection.
4-Chloro-2-methylphenol was detected in the wastewater sludge, final effluent, and a soil column simulating sludge disposal upon agricultural lands at a concentration of 0.12 mg/kg of dry solids, less than 5 ng/l, and 217 ng/l, respectively(1). The average concentration of 4-chloro-2-methylphenol detected in sewage treatment effluents in England and Wales in 1995 was 3.1254 ug/l with a frequency of detection of 47.06 percent(2). The concentration of 4-chloro-2-methylphenol detected in leachate from contaminated groundwater below a landfill in Sorup, Denmark ranged from less than 0.001 ug/l to 0.019 ug/l with a mean concentration of 0.005 ug/l(3). 4-Chloro-2-methylphenol was identified in three leachate samples taken from a municipal landfill in Gryta, Vasteras, Sweden(4). This chemical was detected in agrochemical sewage at a concentration of 2400 ug/l and in secondary sewage effluent at a concentration of 4 ug/l(5).
4-Chloro-2-methylphenol, a biodegradation product of 2-methyl-4-chlorophenoxyacetic acid (MCPA)(1), was detected upon branches sprayed with MCPA, 2 week post application, at a concn of 8,900 ppb and in soils adjacent to the treated railroad bed in Northern Finland at a concn of 337 ppb(2).
Toxicity
LD50 Wistar rat ip 794 mg/kg|LD50 Rat oral 1,190 mg/kg bw|LD50 Mouse oral 1320 mg/kg|LD50 Mouse intravenous 56 mg/kg
/AQUATIC SPECIES/ Trout were exposed to 4-chloro-o-cresol (a metabolite of MCPA) at concentrations of 0.5 or 1.0 ppm for 4 wks. Other fish were exposed to 0.5, 1.0 or 1.5 ppm concentrations for 3 wk periods. Histopathological changes brought about by these exposures were greatest in the gills and kidney. In the gills the changes were remarkable due to lamella telangiectasis in some filaments. It is noted that these changes were not evident in fish kept under 10 and 30 ppm MCPA technical grade solutions.|/AQUATIC SPECIES/ The acute toxicities of several chlorinated phenols, catechols, and cresols, including 4-chloro-o-cresol, to trout were determined. The cresols were lethal in concentrations of 1-2 ppm.|/OTHER TERRESTRIAL SPECIES/ The Frog Embryo Teratogenesis Assay-Xenopus (FETAX) has been applied mainly in pharmacology to examine the toxicity of drugs on embryos (mortality, malformation and growth inhibition). The original FETAX methodology has been modified by us using the in vitro fertilization (ivf) and has been applied to ecotoxicological studies. ...In this preliminary study, we have tested chlorocresol (4-chloro-o-cresol), a soil metabolite of the pesticide MCPA (4-chloro-2-methylphenoxy acetic acid). Embryos were exposed to the chlorocresol (40, 30 mg/l of control FETAX solution) during the cleavage phase. This treatment causes a lethality in concentration-dependent manner. Lethality, evaluated at the end of the test (5 days post fertilization), was due to an high frequency of severe malformed embryos not surviving during the test.
4-Chloro-2-methylphenol's production and use in the production of the herbicide 2-methyl-4-chlorophenoxyacetic acid (MCPA)(1) may result in its release to the environment through various waste streams(SRC). 4-Chloro-2-methylphenol has been identified as an intermediate degradation product of MCPA(2). 4-Chloro-2-methylphenol was detected upon branches sprayed with MCPA, 2 weeks post application, at a concn of 8,900 ppb, and in soils adjacent to the treated railroad bed in Northern Finland at a concn of 337 ppb(3). Thin layer chromatography results indicated that 4-chloro-2-methylphenol is formed in three types of soils by the degradation of carbon-14 ring labeled mecoprop(4). 4-Chloro-2-methylphenol can be isolated as an intermediate in the ozonolysis of MCPA in the dark under irradiation with UV light (>300nm); this may occur during treatment of water containing MCPA with ozone(5).
TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 124 to 645(2), indicate that 4-chloro-2-methylphenol is expected to have moderate mobility in soil(SRC). Volatilization of 4-chloro-2-methylphenol from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.1X10-6 atm-cu m/mole(3). 4-Chloro-2-methylphenol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.40X10-2 mm Hg(3). 4-Chloro-2-methylphenol was almost completely degraded from 2 natural soils treated at 10 ppm within an 8 week incubation period at 25 °C, while nearly a 90 percent reduction occurred after 4 weeks time(4). At a concentration of 200 and 2000 ppm, 12 weeks were required to achieve an approximate 95 percent reduction of initial substrate(4). 4-Chloro-2-methylphenol was degraded similarly in sandy clay and silty clay soils(5). Half-lives were 21 days in both types of soil at initial concentrations of 10 and 1000 ppm each(5). The first order rate constant for the degradation of 3-methyl-4-chlorophenol was 0.0337 in sandy clay soil and 0.0334 in silty clay soil(5). Thus, 4-chloro-2-methylphenol is expected to biodegrade in soil.|AQUATIC FATE: Based on a classification scheme(1), Koc values of 124 to 645(2) indicate that 4-chloro-2-methylphenol is expected to adsorb very little to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.1X10-6 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 40 days and 290 days, respectively(SRC). According to a classification scheme(6), BCF values ranging from 6.4-28(5) and a regression-derived equation(7) suggest the potential for bioconcentration in aquatic organisms is low(SRC). Chlorinated phenols will undergo photolysis in aqueous solutions as a result of ultraviolet irradiation, and that photodegradation leads to the substitution of hydroxyl groups in place of the chlorine atoms with subsequent polymer formation(8). Degradation rates for 4-chloro-2-methylphenol were 2.8 ug/l/day at an initial concentration of 18 ug/l in a sea water shake flask die-away test and 0.04 ug/l/day at an initial concentration of 3.6 ug/l in a waste water shake flask die-away test(9). Mixed cultures of phenol adapted microorganisms exhibited moderate oxygen uptake as the test concentration of 4-chloro-2-methylphenol was reduced from 80 ppm to 50 ppm over a 3 hour period(10,11). An activated sludge pilot plant was operated at 4, 6, and 9 day sludge ages with the same influent settled sewage; higher concentrations of 4-chloro-2-methylphenol were seen in the effluent from the unit run at a 4 day sludge age(12). Based on these studies, 4-chloro-2-methylphenol is expected to biodegrade in the aquatic environment.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-chloro-2-methylphenol, which has a vapor pressure of 2.40X10-2 mm Hg at 25 deg(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 4-chloro-2-methylphenol 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 32 hours(SRC), calculated from its rate constant of 1.2X10-11 cu cm/molecule-sec at 25 °C that was derived using a structure estimation method(3). 4-Chloro-2-methylphenol may undergo direct photolysis due to the absorption of UV light wavelengths above 290 nm(4).
The rate constant for the vapor-phase reaction of 4-chloro-2-methylphenol with photochemically-produced hydroxyl radicals has been estimated as 1.2X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 32 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 4-Chloro-2-methylphenol is not expected to undergo hydrolysis in the environment since phenols are generally resistant to hydrolysis(2,3). Furthermore covalently bonded substituent groups such as the chloro and methyl groups of 4-chloro-2-methylphenol are stable against hydrolysis due to the high negative charge-density of the aromatic nucleus(4). 4-Chloro-2-methylphenol may undergo direct photolysis due to the absorption of UV light wavelengths above 290 nm(5). Similar compounds (chlorophenol, dichlorophenol) have been shown to photodegrade in sunlight or UV light (above 290 nm), but the rate at which photolysis may occur in the environment has not been determined(3,6). Chlorinated phenols will undergo photolysis in aqueous solutions as a result of ultraviolet irradiation, and that photodegradation leads to the substitution of hydroxyl groups in place of the chlorine atoms with subsequent polymer formation(6).
21.38|Bioconcentration tests on carp with an average lipid content of 4.9 percent were conducted in a continuous flow system with six weeks exposure(1). BCF values in carp measured at initial 4-chloro-2-methylphenol concentrations of 2 ug/l and 20 ug/l ranged from 6.4-14 and 8.2-28, respectively(1). According to a classification scheme(2), these BCF ranges suggest the potential for bioconcentration in aquatic organisms is low(SRC).
The Koc values for 4-chloro-2-methylphenol range from 124 to 645(1). According to a classification scheme(2), these Koc values suggest that 4-chloro-2-methylphenol is expected to have moderate mobility in soil.
The Henry's Law constant for 4-chloro-2-methylphenol is 1.1X10-6 atm-cu m/mole(1). This Henry's Law constant indicates that 4-chloro-2-methylphenol is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 40 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 290 days(SRC). 4-Chloro-2-methylphenol's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 4-Chloro-2-methylphenol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure 2.40X10-2 mm Hg(1).
DURING A PILOT STUDY OF THE DISCHARGE OF CHLOROPHENOLS FROM A BIOLOGICAL TREATMENT PLANT FOR MUNICIPAL SEWAGE, WHICH WAS KNOWN TO RECEIVE INDUSTRIAL WASTE WATER CONTAINING CHLOROPHENOLS, EIGHT DIFFERENT CHLOROPHENOLS WERE DETECTED AT LOW LEVELS, INCLUDING 4-CHLORO-2-METHYLPHENOL.
4-Chloro-2-methylphenol, a biodegradation product of 2-methyl-4-chlorophenoxyacetic acid (MCPA)(1), was detected upon potatoes, carrots, green salad and onions grown from fields adjacent to a treated railroad bed in Northern Finland at concn of 0.2, 2.9, 52.9, and 593.0 ppb, respectively, 2 wk post application of MCPA(2).
Occupational exposure to 4-chloro-2-methylphenol may occur through inhalation and dermal contact with this compound at workplaces where 4-chloro-2-methylphenol is produced or used. Monitoring data indicate that the general population may be exposed to 4-chloro-2-methylphenol via ingestion of food. (SRC)
Drug Information
The compounds are absorbed from the gastroenteric tract and from parenteral sites of injection. /Chlorophenols/
An enzyme preparation metabolizing phenoxyacetate herbicides was made from a soil arthrobacter species. Crude extracts degraded 2,4-D, 4-chloro-2-methylphenoxyacetic acid, and 2- and 4-chlorophenoxyacetates. The products formed from 2,4-D, 4-chloro-2-methylphenoxyacetic acid, and 2-, and 4-dichlorophenoxyacetates were identified as 2,4-dichlorophenol, 2-methyl-4-chlorophenol, and 2- and 4-chlorophenols. The bacterial extract was capable of metabolizing catechol and 3-methyl, 4-chloro-, and 3,5-dichlorocatechols.|A bacterium capable of degrading 4-chloro-2-methylphenoxyacetic acid (MCPA) was isolated from soil and identified as flavobacterium peregrinum. Extracts of cells of flavobacterium peregrinum and of a phenoxy-acetate-metabolizing arthrobacter species dehalogenated 4-chloro-2-methylphenoxyacetic acid and several catechols but not 4-chloro-2-methylanisole. An arthrobacter species cell extract was fractionated, and an enzyme preparation was obtained which catalyzed the conversion of 4-chloro-2-methylphenoxyacetic acid to 4-chloro-2-methylphenol. The latter compound was not metabolized unless NADH was added.|Samples (200 g) of a sandy clay soil were incubated with 4-chloro-2-methylphenoxyacetic acid (MCPA) for 0-32 wk at 23 °C. 4-chloro-2-methylphenol was identified as a degradation product of 4-chloro-2-methylphenoxyacetic acid.|The Gram-negative strain S1, isolated from activated sludge, metabolized 4-chloro-2-methylphenol by an inducible pathway via a modified ortho-cleavage route as indicated by a transiently secreted intermediate, identified as 2-methyl-4-carboxymethylenebut-2-en-4-olide by gas chromatography/mass spectrometry. Beside 4-chloro-2-methylphenol only 2,4-dichlorophenol and 4-chlorophenol were totally degraded, without an accumulation of intermediates. The chlorinated phenols tested induced activities of 2,4-dichlorophenol hydroxylase and catechol 1,2-dioxygenase type II. Phenol itself appeared to be degraded more efficiently via a separate, inducible ortho-cleavage pathway. The strain was characterized with respect to its physiological and chemotaxonomic properties. The fatty acid profile, the presence of spermidine as main polyamine, and of ubiquinone Q-10 allowed the allocation of the strain into the alpha-2 subclass of the Proteobacteria. Ochrobactrum anthropi was indicated by fatty acid analysis as the most similar organism, however, differences in a number of physiological features (e.g. absence of nitrate reduction) and pattern of soluble proteins distinguished strain S1 from this species.
0.15 Days
2-Methyl-4-chlorophenol at high concentration decreased the respiration rate of isolated rat liver mitochondria by inhibiting the NAD-dependent dehydrogenases.|The physiological activities of 22 phenols (including 4-chloro-2-methylphenol) were related to various quantum chemical indexes of the compounds. The three factors that seemed to have the most significance for the activity of the phenols were the energy of the highest occupied molecular orbital and the reduced Mulliken overlap populations relative to the oxygen atom and the C-OH bonds.|Chlorinated phenols ...are very effective (...in vitro) as uncouplers of oxidative phosphorylation. They thus prevent incorporation of inorganic phosphate into ATP without affecting electron transport. As a result of this action, which is believed to occur at mitochondrial /srp: membrane/, cells continue to respire but soon are depleted of ATP necessary for growth. /Chlorophenols/
SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes and mucous membranes. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. It can cause irritation of the skin, eyes and mucous membranes. (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)
Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.
Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilation 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/
2,4-MCP
The substance can be absorbed into the body by inhalation, through the skin and by ingestion.
Cough. Laboured breathing. Shortness of breath. Sore throat. Burning sensation.
Skin burns. Pain. Redness.
Pain. Redness. Severe deep burns.
4-Chloro-2-methylphenol Use and Manufacturing
General procedure: an oven-dried Schlenk flask was allowed to cool to room temperature and charged sequentially with arylboronic acid (1 mmol), MeCN (3.0 mL) and silica chloride (0.5 mmol). The reaction was then activated by addition of 30percent HGeneral procedure: The appropriate aryl halide (1 mmol), CsOH (3 mmol), andH2O (1 mL) were added over 0.1 h, to a stirred solutionof CuI (19.0 mg, 10 molpercent) and Dimethylglyoxime (L6;23.2 mg, 20 molpercent) in DMSO (1 mL), and the reactionmixture was stirred at 120 °C (aryl iodides) or (aryl bromides).The progress of the reaction was monitored by TLC(EtOAc–hexane). The reaction mixture was then cooled toroom temperature and acidified with 0.5 M HCl (0.5 mL).The resulting mixture was extracted with EtOAc (3×10 mL)and dried (Na2SO4). Evaporation of the solvent gave a residuethat was purified by column chromatography.General procedure: The appropriate aryl halide (1 mmol), CsOH (3 mmol), andH2O (1 mL) were added over 0.1 h, to a stirred solutionof CuI (19.0 mg, 10 molpercent) and Dimethylglyoxime (L6;23.2 mg, 20 molpercent) in DMSO (1 mL), and the reactionmixture was stirred at 120 °C (aryl iodides) or (aryl bromides).The progress of the reaction was monitored by TLC(EtOAc–hexane). The reaction mixture was then cooled toroom temperature and acidified with 0.5 M HCl (0.5 mL).The resulting mixture was extracted with EtOAc (3×10 mL)and dried (Na2SO4). Evaporation of the solvent gave a residuethat was purified by column chromatography.The opening of the tail gas absorption system, in 2000L enamel in the reactor, the vacuum suction molten 700 kg of O-cresol, in the measuring tank into the perineum 900 kg chloride spare. Opening for stirring the frozen brine cooling to room temperature (25 °C) start instillment sulfuryl chloride, about 5 hours after adding. After the completion of the dropping, the reaction liquid obtained, the reaction liquid heating 45 °C left out of hydrogen chloride and sulfur dioxide vacuum for 30 minutes, to 925 kg 4 - cresol chlorine neighbour, content of 98percent. The exhaust gas generated by the hydrogen chloride by a multi-stage falling-film absorption tower to make hydrochloric acid used for the follow-up process, sulfur dioxide after drying, with the chlorine gas through the catalyst synthesis of the tower, and then cooling to obtain sulfur chloride, recycling.In a 1000 equipped with stirring, thermometer, reflux condenser and dropping funnelAdd 218g o-methylphenol (2 mol, 99percent by mass) into a four-ml bottle.Heated to 65 °C, began to pass chlorine, chlorine gas to 11g (0.15 mol), At the same time adding hydrogen peroxide (content 30percent), 85 g (1.2 moles) of chlorine gas and 80 g (0.7 moles) of oxygen peroxide water, Stop the chlorine gas and add hydrogen peroxide dropwise, continue to hold the heat for 0.5 hours to stop the reaction, keep it standing for stratification, and cool the organic phase to obtain the product.284.3g, HPLC detection mass content 98.5percent, yield 98.2percent; water phase to waste water treatment station.General procedure: o-Cresol (melted) or m-cresol (5.41 g, 50.0 mmol), AlCl3 (0.25 g) and the catalyst (100 mg)were added to a dried 50 ml round-bottomed flask. Sulfuryl chloride (4.66 ml, 57.7 mmol) wasthen added slowly over 2 h via a pressure-equalizing dropping funnel. The reaction mixture wasstirred for 2 h before being quenched with water (20 ml). The reaction mixture was worked up, and the crude products were weighed until constant mass and then analyzed by quantitative GC.Freshly distilled sulfuryl chloride (4.66 mL, 57.7 mmol) was added slowly over 2 h to a mixture of o-cresol or m-cresol (5.41 g, 50 mmol), AlClGeneral procedure: o-Cresol (melted) or m-cresol (5.41 g, 50.0 mmol), AlCl3 (0.25 g) and the catalyst (100 mg)were added to a dried 50 ml round-bottomed flask. Sulfuryl chloride (4.66 ml, 57.7 mmol) wasthen added slowly over 2 h via a pressure-equalizing dropping funnel. The reaction mixture wasstirred for 2 h before being quenched with water (20 ml). The reaction mixture was worked up, and the crude products were weighed until constant mass and then analyzed by quantitative GC.Freshly distilled sulfuryl chloride (4.66 mL, 57.7 mmol) was added slowly over 2 h to a mixture of o-cresol or m-cresol (5.41 g, 50 mmol), AlCl
CHEM INTERMEDIATE, EG, FOR MECOPROP, MCPA & MCPB HERBICIDES; CHEM INTERMEDIATE FOR ITS SODIUM SALT.|Feedstock for the synthesis of pesticides; Additive tracer for resist plasma etching. Disinfectant. Manufacture of the herbicide 4-chloro-2-methylphenoxyacetic acid (MCPA). Exhibits fungicidal activity.|For chloro-ortho-cresol (USEPA/OPP Pesticide Code: 062190) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
Phenol, 4-chloro-2-methyl-: ACTIVE|PHOTOLYSIS OF DILUTE AQUEOUS 4-CHLORO-2-METHYLPHENOXYACETIC ACID (MCPA) SOLUTIONS WITH EITHER SUNLIGHT OR AN INDOOR PHOTOREACTOR YIELDED 4-CHLORO-2-METHYLPHENOL AS THE MAJOR PRODUCT.
THE DETERMINATION OF PHENOLIC CMPD, INCLUDING 4-CHLORO-2-METHYLPHENOL, IN INDUSTRIAL WASTEWATER SAMPLES BY GAS CHROMATOGRAPHY.|DETERMINATION OF 4-CHLORO-2-METHYLPHENOXYACETIC ACID & ITS METABOLITES, 4-CHLORO-2-METHYLPHENOL & 3-METHYL-5-CHLOROCATECHOL BY GAS CHROMATOGRAPHY (GC)/ELECTRON CAPTURE DETECTION (ECD) & GC/MASS SPECTROSCOPY IN BRUSH, SOIL, & VEGETABLE SAMPLES. RESIDUE LEVELS DOWN TO PPB WERE MEASURED BY ECD & VERIFIED BY MASS FRAGMENTOGRAPHY.|THE DETERMINATION OF 4-CHLORO-2-METHYLPHENOL BY THIN-LAYER CHROMATOGRAPHY.|FOUR BIOLOGICAL TREATMENT PLANTS FOR MUNICIPAL SEWAGE, SITUATED AT DIFFERENT LOCATIONS, WERE EXAMINED FOR THEIR CHLOROPHENOL CONTENT, INCLUDING 4-CHLORO-2-METHYLPHENOL, & THEIR ABILITY TO DEGRADE THESE COMPOUNDS. A ROUTINE METHOD FOR THE ANALYSIS OF BOTH LOW- & HIGH-CHLORINATED PHENOLS WAS DEVELOPED, BASED ON GAS CHROMATOGRAPHY WITH ELECTRON-CAPTURE DETECTION (GC-ECD). THE METHOD WAS EVALUATED BY COMPARING THE GC-ECD RESULTS WITH THOSE OBTAINED BY COMBINED GAS CHROMATOGRAPHY-MASS SPECTROMETRY WITH SELECTED ION-MONITORING OF THE MOLECULAR IONS OF THE SPECIFIC PHENOLS. THE TOTAL PHENOL CONTENT, DETERMINED BY GC-ECD SHOWED A GOOD CORRELATION WITH THE PHENOL NUMBER, OBTAINED BY USING THE 4-AMINOANTIPYRINE METHOD.|For more Analytic Laboratory Methods (Complete) data for 4-CHLORO-2-METHYLPHENOL (6 total), please visit the HSDB record page.
Environmental transformation -> Pesticide transformation products (metabolite, successor)
2-methyl-4-chlorophenol is a known environmental transformation product of MCPA and mecoprop.|2-methyl-4-chlorophenol is a known environmental transformation product of MCPA and Mecoprop-P.
Computed Properties
Molecular Weight:142.58
XLogP3:2.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:142.0185425
Monoisotopic Mass:142.0185425
Topological Polar Surface Area:20.2
Heavy Atom Count:9
Complexity:94.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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