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P-Chlorophenol(CAS No. 106-48-9)

P-Chlorophenol C6H5ClO (cas 106-48-9) Molecular Structure

106-48-9 Structure

Identification and Related Records

【Name】
P-Chlorophenol
【Iupac name】
4-chlorophenol
【CAS Registry number】
106-48-9
【Synonyms】
4-Chlorophenol solution
Parachlorophenol
Para chlorophenol
4-chloro phenol
4-chloro-1-hydroxybenzene
4-chloro-pheno
4-Chlorophenol(form2)
4-chloro-phenole
Applied 3-78
applied3-78
chlorophenols,solid
p-Chlorfenol
P-CHLORO PHENOL
4-Hydroxychlorobenzene
【EINECS(EC#)】
203-402-6
【Molecular Formula】
C6H5ClO (Products with the same molecular formula)
【Molecular Weight】
128.56
【Inchi】
InChI=1/C6H5ClO/c7-5-1-3-6(8)4-2-5/h1-4,8H
【InChIKey】
WXNZTHHGJRFXKQ-UHFFFAOYSA-N
【Canonical SMILES】
C1=CC(=CC=C1O)Cl
【MOL File】
106-48-9.mol

Chemical and Physical Properties

【Appearance】
off-white to light tan crystals or powder
【Density】
1.306
【Melting Point】
41-45℃
【Boiling Point】
220℃
【Vapour】
0.245mmHg at 25°C
【Refractive Index】
1.5579
【Flash Point】
121℃
【Water】
2.7 g/100 mL (20℃)
【Solubilities】
Soluble
【Color/Form】
Needle like, white to straw-colored crystals
White crystals (yellow or pink when impure)
Yellow solid
【Stability】
Stable. Incompatible with acid chlorides, acid anhydrides, oxidizing agents, iron.
【HS Code】
29081000
【Storage temp】
0-6°C
【Spectral properties】
Index of refraction: 1.5419 at 55 deg C/D; 1.5579 at 40 deg C/D
MAX ABSORPTION (CYCLOHEXANE): 224 NM (LOG E= 3.94); 279 NM (LOG E= 3.27); 287 NM (LOG E= 3.23); SADTLER REF NUMBER: 1418 (IR, PRISM); 243 (IR, GRATING)
IR: 4814 (Coblentz Society Spectral Collection)
UV: 409 (Sadtler Research Laboratories Spectral Collection)
NMR: 17044 (Sadtler Research Laboratories Spectral Collection)
MASS: 69778 (NIST/EPA/MSDC Mass Spectral Database, 1990 version)
Intense mass spectral peaks: 128 m/z (100%), 130 m/z (33%), 65 m/z (42%), 64 m/z (20%)
【Computed Properties】
Molecular Weight:128.5563 [g/mol]
Molecular Formula:C6H5ClO
XLogP3:2.4
H-Bond Donor:1
H-Bond Acceptor:1
Rotatable Bond Count:0
Tautomer Count:2
Exact Mass:128.002892
MonoIsotopic Mass:128.002892
Topological Polar Surface Area:20.2
Heavy Atom Count:8
Formal Charge:0
Complexity:66.9
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Donor Count:1
Feature 3D Ring Count:1
Effective Rotor Count:0
Conformer Sampling RMSD:0.4
CID Conformer Count:1

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R20/21/22;R51/53
【Safety Statements 】
S28;S61
【HazardClass】
6.1
【Safety】

Poison by inhalation and intraperitoneal routes. Moderately toxic by ingestion, skin contact, and subcutaneous routes. A severe skin and eye irritant. Human systemic effects by inhalation: excitement, irritability. Mutation data reported. Combustible when exposed to heat or flame. To fight fire, use water, spray, mist, fog, foam, dry chemical. When heated to decomposition it emits toxic fumes of Cl?.
Hazard Codes:?HarmfulXn,DangerousN
Risk Statements: 20/21/22-51/53-50?
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.?
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?
R50:Very toxic to aquatic organisms.
Safety Statements: 28-61-28A-24/25-60?
S28:After contact with skin, wash immediately with plenty of soap-suds.?
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.?
S24/25:Avoid contact with skin and eyes.?
S60:This material and its container must be disposed of as hazardous waste.
RIDADR: UN 2020 6.1/PG 3
WGK Germany: 2
RTECS: SK2800000
HazardClass: 6.1
PackingGroup of 4-Chlorophenol (CAS NO.106-48-9): III

【PackingGroup 】
III
【Sensitive】
Air Sensitive
【Skin, Eye, and Respiratory Irritations】
Strong irritant to tissue
The substance irritates the eyes, the skin and the respiratory tract.
Causes severe eye and skin burns.
【Cleanup Methods】
Phenolic cmpd in wastewater are oxidized with hydrogen peroxide catalyzed by iron(3+)-iron(2+). When the wt ratio of phenol:hydrogen peroxide is 1:3 and iron 5-100 ppm, more than 95% of the phenols are removed in 30 min from a 500 ppm phenol soln at pH 5-6 and 25-50 deg C. /Phenolic cmpd/
Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Ventilate area of spill or leak. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or a similar material and deposit in sealed containers. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. It may be necessary to contain and dispose of this chemical as a hazardous waste. /Monochlorophenols/
Shovel into suitable dry container.
【Transport】
UN 2904/2905/2020
【Fire Fighting Procedures】
WATER, SPRAY, MIST, FOG, FOAM, DRY CHEMICAL
Use dry chemical, carbon dioxide, or foam extinguishers. Vapors are heavier than air and well collect in low areas. ... Vapors in confined areas may explode when exposed to fire. Containers may explode in fire. Storage containers and parts of containers may rocket great distances, in many directions. ...From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. /Monochlorophenols/
Use dry chemical foam, carbon dioxide, or water spray. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products. Use water spray to keep fire-exposed containers cool.
【Fire Potential】
COMBUSTIBLE WHEN EXPOSED TO HEAT OR FLAME
【Formulations/Preparations】
Grade: NF, technical
【DOT Emergency Guidelines】
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. 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. /Chlorophenols, liquid; Chlorophenols, solid/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Chlorophenols, liquid; Chlorophenols, solid/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (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. Ventilate enclosed areas. /Chlorophenols, liquid; Chlorophenols, solid/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (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. /Chlorophenols, liquid; Chlorophenols, solid/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Evacuation: ... 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. /Chlorophenols, liquid; Chlorophenols, solid/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire: Small fires: Dry chemical, CO2 or water spray. Large fires: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire control water for later disposal; do not scatter the material. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. /Chlorophenols, liquid; Chlorophenols, solid/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. /Chlorophenols, liquid; Chlorophenols, solid/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. /Chlorophenols, liquid; Chlorophenols, solid/
【Other Preventative Measures】
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.
Wash contaminated areas of skin with concentrated soap solution without delay. Contaminated gloves, clothing, shoes should be immediately removed and disposed of in an incinerator.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
【Protective Equipment and Clothing】
/Wear/ face shield; Boots and apron; Respiratory protection
Wear protective gloves and clothing to prevent any reasonable probability of skin contact. Safety equipment suppliers/manufacturers can provide recommendations on the most protective glove/clothing material for your operation. All protective clothing (suits, gloves, footwear, headgear) should be clean, available each day, and put on before work. Contact lenses should not be worn when working with this chemical. Wear splash-proof chemical goggles and face shield when working with liquid, unless full facepiece respiratory protection is worn. Wear dust-proof goggles when working with powders or dust, unless full facepiece respiratory protection is worn. Employees should wash immediately with soap when skin is wet or contaminated. Provide emergency showers and eyewash. /Monochlorophenols/
Wear special protective clothing and positive pressure self-contained breathing apparatus.
ENGINEERING CONTROLS Use only in a chemical fume hood. Safety shower and eye bath.
【Specification】

? 4-Chlorophenol (CAS NO.106-48-9), its Synonyms are Parachlorophenol ; Phenol, 4-chloro- ; p-Chlorophenol ; 4-Chloro-1-hydroxybenzene ; 4-Hydroxychlorobenzene ; 4-Monochlorophenol ; Phenol, p-chloro- ; p-Chlorophenic acid . It is off-white to light tan crystals or powder.

【Octanol/Water Partition Coefficient】
log Kow = 2.39
【Report】

Reported in EPA TSCA Inventory. Chlorophenol compounds are on the Community Right-To-Know List.

【Disposal Methods】
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.
Chemical Treatability of p-Chlorophenol; Concentration Process: Biological Treatment; Chemical Classification: Phenols; Scale of Study: Unknown; Type of Wastewater Used: Pure Compound (one solute in a solvent); Results of Study: 96% reduction based on chemical oxygen demand, rate of biodegradation 11 mg/g hr; (Activated Sludge Process).
Chemical Treatability of p-Chlorophenol; Concentration Process: Biological Treatment; Chemical Classification: Phenols; Scale of Study: Laboratory Scale; Type of Wastewater Used: Pure Compound (one solute in a solvent); Results of Study: 100% reduction in 33 hours; (Biodegradation by mutant pseudomonas species).
This work presents the results of the application of an optimally controlled influent flow rate strategy to biodegrade, in a discontinuous reactor, high concentrations of 4-chlorophenol used as toxic compound model. The influent is fed into the reactor in such a way as to obtain the maximal degradation rate, thus avoiding the inhibition of the microorganisms. The optimal strategy was able to manage increments of toxic concentrations in the influent up to 7,000 mg 4CP/L without any problem. It was shown not only that higher concentrations of toxic could be treated, but also that a reduction in degradation time (around 52%) and in the supplied air volume was obtained. [Moreno-Andrade I et al; Water Sci Technol 53 (11): 261-8 (2006)] PubMed Abstract
The aim ... is to study a coupled system to treat biorecalcitrant wastewaters. The combination consists of an advanced oxidation process (AOP) named photo-Fenton (Ph-F), which is a photochemical treatment and a sequencing batch biofilter reactor (SBBR). The synthetic wastewater used to optimize this process is a solution of 200 ppm of 4-chlorophenol (4-CP)... The results showed that it is necessary to severely treat the toxic solution (with 500 ppm of [H2O2]0) in order to achieve more than 90% of TOC removal in the whole process. The photochemical and biological treatments lasted 50 minutes and 24 hours, respectively. [Bacardit J et al; Water Sci Technol 55 (12): 95-100 (2007)] PubMed Abstract
Treatment of simulated wastewater containing 40 mg/L of 4-chlorophenol (4-CP) was carried out in an upflow anaerobic sludge blanket (UASB) reactor under methanogenic condition. The performance of this test UASB reactor was evaluated in terms of 4-CP removal. Hydraulic retention time (HRT) and substrate:co-substrate ratio for the 4-CP removal was optimized by varying the influent flow rate (13-34.7 ml/min) and sodium acetate concentration (2-5 g/L), respectively ... [Majumder PS, Gupta SK; Bioresour Technol 99 (10): 4169-77 (2008)] PubMed Abstract
A) Dissolve in such combustible solvent as alcohols, benzene etc. Spray the solvent into the furnace with afterburner and scrubber. B) Pour into sodium bicarbonate or a mixture of sand-soda ash (9:1). After mixing, transfer into a paper carton filled with packing paper. Burn more efficiently in the furnace with an afterburner and scrubber. Recommendable method: Incineration. Not recommendable method: Discharge to sewer.
The biosurfactant's effect on the biodegradation of 4-chlorophenol (4-CP) in the existence of glucose was researched under the circumstances of using unacclimated culture and various sludge ages. The removal efficiencies of chemical oxygen demand (COD) and 4-CP, the growth of biomass and specific substrate removal rates were examined under various operating conditions.... [Uysal A, Turkman A; J Hazard Mater 148 (1-2): 151-7 (2007)] PubMed Abstract
TiO(2) photocatalyst (P-25) (50 mg/L) was tentatively introduced into pulsed high-voltage discharge process for non-thermal plasma-induced photocatalytic degradation of the representative mode organic pollutant parachlorophenol (4-CP), including other compounds phenol and methyl red in water.... The introduction of TiO(2) photocatalyst into pulsed discharge plasma process in the utilizing of ultraviolet radiation and electric field in pulsed discharge plasma process enhanced the yields of chemically active species, which were available for highly efficient removal and mineralization of organic pollutants. [Hao XL et al; J Hazard Mater 141 (3): 475-82 (2007)] PubMed Abstract
2-Chlorophenol (2-CP), 4-chlorophenol (4-CP) and 2,4-dichlorophenol (2,4-DCP) at initial concentrations of 10, 20, 50 and 100 mg/L were degraded in aqueous media by direct UV photolysis using dielectric barrier discharge XeBr(*) excilamp (283nm) in a flow-through photoreactor. The pseudo-first order rate constants were highest and half-life times were lowest for 4-CP. The rates of photolysis under the experimental conditions increased in the order: 2-CPPubMed Abstract

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Chlorination of phenol; from chloroaniline through diazonium salt
... From diazotized p-chloroaniline by chlorination of phenol.
Mfr by selective reduction of chlorobromophenols..
From p-nitrosophenol by a modification of Sandmeyer reaction.
Phenol + sulphuryl chloride (ring chlorination)
The chlorination of melted phenol using chlorine gas yields a mixture of ortho and para monochlorophenols with an ortho/para ratio of about 0.54 (35/65), which is scarcely dependent on temperature. The distribution between the two isomers depends especially on the nature of the chlorination reagent and the characteristics of the reaction medium. The formation of 2-chlorophenol is favored by an aprotic nonpolar solvent medium, such as hexane, carbon tetrachloride, or dichloroethane. The ortho/para ratio is also higher for reactions with a low concentration of phenol and a high temperature. The chlorination of a 5% solution of phenol in perchloroethylene at 110 deg C in the presence of 0.01 wt% diisopropylamine gives a very high ortho/para ratio, about 15. Chlorinations using aqueous sodium hypochlorite at pH 10, tert-butyl hypochlorite and alkali phenolates dispersed in an anhydrous medium, or chlorine in acetic acid in the presence of acetic anhydride also favor the formation of 2-chlorophenol. The formation of 4-chlorophenol is favored by chlorination in a polar medium, such as acetonitrile, nitrobenzene, or ether. Substitution in the para position is also strongly favored by the use of sulfuryl chloride as a chlorinating agent (ortho/para = 0.35).
U.S. Production

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 1986 >500 thousand - 1 million 1990 10 thousand - 500 thousand 1994 10 thousand - 500 thousand 1998 10 thousand - 500 thousand 2002 10 thousand - 500 thousand
【Usage】

Intermediates of Liquid Crystals

Biomedical Effects and Toxicity

【Pharmacological Action】
- 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.
【Therapeutic Uses】
Local antibacterial agent in root canal therapy
Topical antiseptic /cat/
Medication (Vet): /Formerly/ as topical antiseptic in ointments
【Biomedical Effects and Toxicity】
A number of rabbit studies have shown that metabolism of the monochlorophenols is principally via conjugation. In one study, groups of 6 rabbits were treated by gavage with 171.3 mg/kg of 2-CP or 4-CP emulsified in water as a single dose. For both isomers, the 24-hour urine analysis indicated that between 78.1 and 88.3% of the administered dose was excreted as the glucuronide, and between 12.8 and 20.6% of the administered dose was excreted as the ethereal sulfate. A total of 101.7 and 101.1% of the administered 2-CP or 4-CP doses, respectively, was accounted for as urinary glucuronide and sulfate conjugates.
Metabolism was ... investigated in 4 rabbits, each treated by gavage with an average dose of 395 mg/kg/day of 4-CP. After 36 hours, 54.1% of the administered dose appeared in the urine as the glucuronide conjugate, and 10.4% of the administered dose appeared in the ethereal sulfate fraction. Only 0.1% of the administered dose was excreted as 4-chlorocatechol. The low total recovery (64.5%) in the latter experiment limits conclusions.
In a limited study in dogs about half of an oral dose of 2- or 4-CP was excreted in the urine as the ethereal sulfate. No evidence for metabolism to mercapturic acid was found.
... Absorbed from ... gastrointestinal tract & ... parenteral sites of injection. ... Excreted as conjugates of sulfuric & glucuronic acid. ... Urine darkens after standing /Chlorophenols/

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an experimental Koc value range of 70 to 485.6(2-4), indicates that 4-chlorophenol is expected to have high to moderate mobility in soil(SRC). The pKa of 4-chlorophenol is 9.41(5), indicating that this compound will partially exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(6). Volatilization of 4-chlorophenol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.3X10-7 atm-cu m/mole for the neutral species(SRC) derived from its vapor pressure, 8.90X10-2 mm Hg(7), and water solubility, 2.40X10+4 mg/L(8). 4-Chlorophenol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 8.2X10-2 mm Hg(7). 4-Chlorophenol reached 2% of its theoretical BOD using activated sludge in the Japanese MITI test(9) while complete degradation was reported within 3 days in acclimated sludges(10,11). 4-Chlorophenol degraded in clay and silt loams soils from 84-100% in 3-16 days(12-14) and 22.2% and 35% in 1 and 10 weeks, respectively, in para-brown soil(15). These data suggest that biodegradation of 4-chlorophenol in soils is variable depending on conditions(SRC).
AQUATIC FATE: Based on a classification scheme(1), an experimental Koc value range of 70 to 485.6(2-4), indicates that 4-chlorophenol may exhibit low to moderate absorption to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(5) based upon an estimated Henry's Law constant of 6.3X10-7 atm-cu m/mole for the neutral species(SRC) derived from its vapor pressure, 8.90X10-2 mm Hg(6), and water solubility, 2.40X10+4 mg/L(7). According to a classification scheme(8), a BCF range of 6.0-18(6,9, 10) suggests the potential for bioconcentration in aquatic organisms is low(SRC). 4-Chlorophenol undergoes flash-induced aquatic photolysis in both aerated and non-aerated solns(11) and photolytic oxidation by UV/ozone(12). Biodegradation of 4-chlorophenol in water varies depending on the conditions. Complete removals have been reported in water after 13 days for acclimated water(13) and 30 days in farm stream sediment(14), 44% degradation after 5 days(15) and 33% after 25 days in non-acclimated water(13). These data suggest that biodegradation will vary depending on the conditions(SRC). Since the pKa of 4-chlorophenol is 9.41(16), it will exist in water and sediment in a partially dissociated state which may effect its transport and reactivity in water and sediment(SRC). The suggested half-life of 4-chlorophenol in water is 55 hours(6), although it is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(17).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-chlorophenol, which has a vapor pressure of 8.90X10-2 mm Hg at 25 deg C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 4-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 3.3 days(SRC), calculated from its rate constant of 9.9X10-12 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(3). The quantum yield for the disappearance of 4-chlorophenol was 0.25 when it was irradiated at 296 nm in aqueous solution at pH 1-13; products of photolysis included hydroquinone(4).

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