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Home > Encyclopedia > 4-Chlorophenyl phenyl ether

4-Chlorophenyl phenyl ether

4-Chlorophenyl phenyl ether structure

4-Chlorophenyl phenyl ether 

structure
  • CAS No:

    7005-72-3

  • Formula:

    C12H9ClO

  • Chemical Name:

    4-Chlorophenyl phenyl ether

  • Synonyms:

    Benzene,1-chloro-4-phenoxy-;Ether,p-chlorophenyl phenyl;1-Chloro-4-phenoxybenzene;p-Chlorodiphenyl oxide;p-Chlorophenyl phenyl ether;4-Chlorophenyl phenyl ether;4-Chlorodiphenyl ether;NSC 61839;PCDE 3;p-Phenoxychlorobenzene;CDE 3

Description

colorless to light yellow liquid


4-chlorophenyl phenyl ether appears as liquid. Density 1.193 g / cm3. Insoluble or slightly soluble in water.


4-chlorophenyl phenyl ether appears as liquid. Density 1.193 g / cm3. Insoluble or slightly soluble in water.

4-Chlorophenyl phenyl ether Basic Attributes

204.652

204.65

230-281-7

5AY689Y3GH

61839

3271

DTXSID2052447

Characteristics

9.23000

4.81

4-chlorophenyl phenyl ether appears as liquid. Density 1.193 g / cm3. Insoluble or slightly soluble in water.

1.2026 g/cm3 @ Temp: 15 °C

-8 °C

5-284 °C

128.1±13.9 °C

1.584

3.3 mg/L (25 ºC)

2.7 x 10 -3 mmHg at 25 °C (calculated, Branson, 1977)

Insoluble or slightly soluble in water.

Ethers

Peroxidizable Compound

4-CHLOROPHENYL PHENYL ETHER oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154, 164].

Safety Information

UN 3082 9/PG 3

3

R36/37/38;R50/53

S61-S37/39-S29-S26-S60-S36/37/39

Xi:Irritant;N:Dangerousfortheenvironment;

P273-P280-P305 + P351 + P338-P501

H302-H317-H318-H410

Combustible. (NTP, 1992)|Flammable - 2nd degree

|Danger|H302 (75%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P272, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 5 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

A fire in your laboratory involving this chemical should be extinguished with a dry chemical, carbon dioxide or halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong 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 protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store it in a freezer. (NTP, 1992)

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. RECOMMENDED GLOVE MATERIALS: Permeation data indicate that nitrile gloves may provide protection to contact with this compound. Nitrile over latex gloves is recommended. However, if this chemical makes contact with your gloves, or if a tear, hole or puncture develops, remove them at once. (NTP, 1992)

TREATABILITY OF WASTEWATER POLLUTANTS, P-CHLOROPHENYL PHENYL ETHER, BY SOLVENT EXTRACTION IS DISCUSSED.|Adsorption capacities of activated carbon for /wastewater pollutants/: 4-chlorophenyl phenyl ether 111 mg/g. /From table/

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

U.S. EPA Storet Data Base, 1,333 samples, 1.1% positive, median concn less than 10 ug/L(1). 4-Chlorophenyl phenyl ether was not detected in 86 samples from 51 stormwater catchments located throughout the USA (detection limits not given)(2).

4-Chlorophenyl phenyl ether was not detected in sediment samples from the western basin of Lake Ontario, near the mouth of the Niagara River (detection limits not given)(1). U.S. EPA Storet Data Base, 344 samples, 0% positive, median concn less than 500 ug/L(2). A ratio for 4-chlorophenyl phenyl ether defined as the amount bound to suspended solids/sediment vs the amount in water was reported as 4:1(3).

Toxicity

4-Chlorophenyl phenyl ether is an anthropogenic compound, and is not known to exist in nature. (SRC)

The 1977 TSCA inventory listed one company which produced 4-chlorophenyl phenyl ether. Production volume was listed as one hundred thousand to one million pounds(1). More current production volumes could not be found(SRC). 4-Chlorophenyl phenyl ether was developed in search of a dielectric fluid to replace PCB's, and finds use in capacitors(2), which may result in environmental release during production, use, or disposal(SRC).

TERRESTRIAL FATE: If released to soil, 4-chlorophenyl phenyl ether should be expected to undergo biodegradation(1,2,3). Based on the log octanol/water partition coefficient (Kow) for 4-chlorophenyl phenyl ether, and on the water solubility(1), Koc values can be calculated to fall in the range 2260-3950(4,SRC), suggesting slight mobility in soil(5,SRC). Consideration of the Henry's Law constant, 8.4X10-4 atm cu-m/mol(1), suggests that volatilization from moist soil might be an important fate process(SRC).|AQUATIC FATE: If released to water, 4-chlorophenyl phenyl ether should be expected to undergo biodegradation(1,2,3). 4-Chlorophenyl phenyl ether has an absorption maximum centered at 293 nm (in methanol)(5), and thus should undergo direct photochemical degradation in the upper layer of surface water(SRC). Based on laboratory rate constants obtained for 4-chlorophenyl phenyl ether in water, the calculated half-life in surface waters at 40 deg lattitude is 200 days (summer) and greater than 400 days (winter)(1). Based on the Henry's Law constant for 4-chlorophenyl phenyl ether, 8.4X10-4 atm cu-m/mol at 25 °C(1), volatilization from water should be an active fate process(SRC). The estimated volatilization half-life for a model river is 6 hours(6,SRC). The estimated volatilization from a model pond, which takes into account adsorption processes, is 39 days(7,SRC). 4-Chlorophenyl phenyl ether should not undergo hydrolysis, but should be expected to adsorb to sediment and suspended matter(SRC). An experimentally determined BCF for rainbow trout, 736(1), demonstrates that bioaccumulation in aquatic organisms can occur(SRC).|ATMOSPHERIC FATE: If released to the atmosphere, 4-chlorophenyl phenyl ether, which has a maximum UV absorption at 293 nm (in methanol)(1), would be expected to undergo direct photochemical degradation(1,SRC). The estimated half-life for the reaction with photochemically produced hydroxyl radicals in the atmosphere is 1.3 days(2,SRC).|AQUATIC FATE: It is not possible to determine the most probable aquatic fate for 4-chlorophenyl phenyl ether from available data. This pollutant is reported to be rapidly degraded by acclimated sewage sludge, but biodegradation data from river water die away experiments indicate that this cmpd has a potential for persistence in natural surface waters. Sorption by organic rich sediments & bioaccumulation in fish have been demonstrated. Although photolysis may make a minor contribution to the degradation of this pollutant near the air water surface, oxidation & hydrolysis are probably not important as fate processes. The role of volatilization is uncertain.

The UV spectra of 4-chlorophenyl phenyl ether in methanol has a lambda max at 279 and at 293 nm, suggesting that direct photochemical degradation in the atmosphere and in the upper layer of surface water may be an important fate process(1,SRC). Based on laboratory rate constants obtained for 4-chlorophenyl phenyl ether in water, the calculated half-life in surface waters at 40 deg latitude is 200 days (summer) and greater than 400 days (winter)(1). 4-Chlorophenyl phenyl ether underwent 1.8% and 38% photoreaction in a degassed methanol solution using a rayonet photolysis apparatus after 8 and 88 hours, respectively(2). The estimated half-life for the atmospheric reaction with photochemically produced hydroxyl radicals is 1.3 days(3,SRC).

A BCF of 736 was experimentally determined for 4-chlorophenyl phenyl ether in rainbow trout (Salmo gairdneri) (8.9 day experiment)(1).

Based on the log octanol/water partition coefficient (Kow) of 4.08, and the water solubility, 3.3 ppm at 25 °C(1), estimates for Koc are in the range 2260-3950 for 4-chlorophenyl phenyl ether(2,3,SRC), suggesting slight mobility in soil(4,SRC).|... The polar nature of the ether bond & the carbon-halogen bond, coupled with the cmpd's miscibility with most lipophilic material ensures sorption of 4-chlorophenyl phenyl ether by organic detritus. Adsorption by clay particles is also thought to be highly probable, inasmuch as the polarity & planar geometry of this molecule should facilitate its intercalation within the layered clay structure. Evidence for sorption by suspended organic material is given by a sediment to water distributional ratio of 4:1 during biodegradation studies with sludge.

An estimated evaporation rate constant for 4-chlorophenyl phenyl ether from Lake Michigan is given as 7.0 cm/hour(1). The estimated volatilization half-life for a model river 1 m deep, flowing at 1 m/sec, and a wind velocity of 3 m/sec is 5.7 hours(2,SRC). The estimated volatilization from a model pond, which takes into account adsorption processes, is 39 days(3,SRC).

SURFACE WATER: U.S. EPA Storet Data Base, for 4-chlorophenyl phenyl ether 837 samples, 0.2% positive, median concn less than 10 ug/l(1). Identified in two samples of water from the River Lee, United Kingdom, in concn less than 0.1 ug/l(2). Detected in 4 of 150 raw water extracts and 8 out of 155 finished water extracts at 11 water utilities in the Ohio River Basin, 1977-78, at concn of approx 0.2 ug/l (may have been up to 1 ug/l)(3). Not detected in 86 samples from 51 rainwater runoff catchments located throughout the USA (detection limits not given)(4).

The probable routes of exposure for 4-chloropheny phenyl ether are by inhalation and dermal contact during its manufacture and use as a dielectric fluid. The general public should not be expected to be exposed to this compound unless it is accidentally released to the environment. (SRC)

Drug Information

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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. 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. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure 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)

4-CDE

4-Chlorophenyl phenyl ether Use and Manufacturing

Methods of Manufacturing

SOME HALOGENATED DIPHENYL ETHERS CAN BE PREPARED BY DIRECT HALOGENATION OF DIPHENYL CATALYZED BY LEWIS ACIDS & BY DEAMINATION OF NITRO & AMINO SUBSTITUTED DIPHENYL ETHERS. /HALOGENATED DIPHENYL ETHERS/

Benzene, 1-chloro-4-phenoxy-: ACTIVE

EPA Method 611: Haloethers. A gas chromatography method for the analysis of p-chlorophenyl phenyl ether in municipal and industrial discharges, consists of a glass column, 1.8 m x 2 mm ID, packed with Supelcoport (100/120 mesh) coated with 3% SP-1000, with a halide specific detector (electrolytic conductivity or microcoulometric), and helium as the carrier gas at a flow rate of 40 ml/min. A sample injection volume of 2 to 5 ul is suggested, the column temperature is held isothermal at 60 °C for two min after injection then programmed at 8 °C/min to 230 °C and held for four min. This method has a detection limit of 3.9 ug/l and an overall precision of 0.41 times the average recovery + 0.55, over a working range of 1.0 to 626 ug/l.|EPA Method 625: Acid/Base/Neutral Extractables. A gas chromatography/mass spectrometry method for the analysis of p-chlorophenyl phenyl ether in municipal and industrial discharges, consists of a glass column, 1.8 m x 2 mm ID, packed with Supelcoport (100/120 mesh) coated with 3% SP-2250, with the detection performed by the mass spectrometer, and helium as the carrier gas at a flow rate of 30 ml/min. A sample injection volume of 2 to 5 ul is suggested, the column temperature is held isothermal at 50 °C for 4 min and then programmed immediately at 8 deg/min to a final temperature of 270 °C. This method has a detection limit of 4.2 ug/l and an overall precision of 0.30 times the average recovery + 0.46, over a working range of 5 to 1300 ug/l.|EPA Method 1625: Semivolatile Organic Compounds. An isotope dilution gas chromatography/mass spectrometry method for the determination of semivolatile organic compounds in municipal and industrial discharges, this method is designed to meet the survey requirements of Effluent Guidelines Division (EGD) and the National Pollution Discharge Elimination System (NPDES). Under the prescribed conditions, unlabeled p-chlorophenyl phenyl ether has a detection limit of 10 ug/l and a mean retention time of 1409 sec. This method has an initial precision of 42 ug/l and an accuracy of 75-166 ug/l for the unlabeled compound.

Fire Hazards -> Flammable - 2nd degree

Computed Properties

Molecular Weight:204.65
XLogP3:4.3
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:204.0341926
Monoisotopic Mass:204.0341926
Topological Polar Surface Area:9.2
Heavy Atom Count:14
Complexity:158
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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