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4-Chlorophenyl phenyl ether

HCID 23436
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
55398-86-2
Standard SMILES
Clc1ccc(Oc2ccccc2)cc1
InChIKey
PGPNJCAMHOJTEF-UHFFFAOYSA-N
Molecular formula
C12H9ClO
Average molar mass
204.65 g/mol
Monoisotopic mass
204.03419259

Overview

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

Names & identifiers

Preferred name
4-Chlorophenyl phenyl ether
IUPAC
1-chloro-4-phenoxybenzene
English name
1 -Chloro-4-phenoxybenzene
Molecular formula
C12H9ClO
Molecular weight
204.65226

Names & synonyms

4-Chlorodiphenyl ether7005-72-34-Chlorophenyl phenyl etherBenzene, 1-chloro-4-phenoxy-p-Chlorodiphenyl oxideEther, p-chlorophenyl phenylP-CHLOROPHENYL PHENYL ETHERChlorodiphenyl etherMonochlorodiphenyl oxideDTXSID20524474-Monochlorodiphenyl oxide5AY689Y3GH
Show more names
NSC-61839DTXCID4031019RefChem:985774-CDE230-281-71-Chloro-4-phenoxybenzeneMONOCHLOROPHENYL ETHER1-chloro-4-phenoxy-benzene

Database identifiers

CAS
55398-86-2、7005-72-3
PubChem CID
23436
DTXSID
DTXSID2052447
UNII
5AY689Y3GH
EC Number
230-281-7
Nikkaji
J45.879A

Properties

Computed structural properties

XLogP
4.3
Topological polar surface area
9.2 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
14
Formal charge
0
Complexity
158

Experimental & physicochemical properties

Chemical Classes · 2 items

Flammable agents - 2nd degree

Semi-Volatile Organic Compound (SVOC)

PolymersOther Classes -> Halogenated Polyaromatics
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogPlog Kow= 4.08
Density · 3 items

1.2026 at 59 °F (NTP, 1992) - Denser than water; will sink

1.2026 @ 15 °C

1.2026 @15°C

Solubility3.3 mg/l @ 25 °C
Boiling Point · 2 items

543 to 545 °F at 760 mmHg (NTP, 1992)

284-5 °C

Melting Point · 2 items

-8 °C

-8 °C

Vapor Pressure · 3 items

0.0027 [mmHg]

0.0027 torr @ 25 °C (calc)

0.0027 [mm Hg] @25 °C

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 16.7% (1 of 6) of reports.

Danger

H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 6 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

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

Hazard Traits - Environmental tox

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Fire HazardsCombustible. (NTP, 1992)
Hazards SummaryMay form unstable pyrophoric peroxides on exposure to air; [CAMEO] See Hexachlorodiphenyloxide.
Reactive GroupEthers
Reactivity AlertsPeroxidizable Compound
Reactivity Profile4-CHLOROPHENYL PHENYL ETHER oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154, 164].
Air and Water ReactionsInsoluble or slightly soluble in water.

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Used as dielectric fluid; [HSDB]

Dielectric fluid

Methods of ManufacturingSOME 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/
General Manufacturing InformationBenzene, 1-chloro-4-phenoxy-: ACTIVE

Suppliers1 total

厦门盈融达化工有限公司+86-0592-6210733 · [email protected]

Related reactions

10 records
New reaction record
HRID 187821 reaction equation
HRID 187821As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 380583 reaction equation
HRID 380583As reactantuspto-grants-2001_10
HRID 687294 reaction equation
HRID 687294As reactantTraining data from https://doi.org/10.1039/C8SC04228D (3/10)
HRID 1220003 reaction equation
HRID 1220003As reactantTraining data from https://doi.org/10.1039/C8SC04228D (5/10)
HRID 1251473 reaction equation
HRID 1251473As reactantuspto-grants-2002_01
HRID 1531234 reaction equation
HRID 1531234As reactantuspto-grants-2001_03
HRID 1703435 reaction equation
HRID 1703435As productuspto-grants-1978_11
HRID 1764171 reaction equation
HRID 1764171As reactantuspto-grants-1978_09
Page 1 of 2

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Refractive Index
Index of refraction: 1.599
Physical Description · 2 items

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

Liquid; [CAMEO] Colorless liquid; [MSDSonline]

Physicochemical properties

Melting point
-8 °C · -8 °C
Boiling point
5 · 5-284 °C
Density
1.2026 g/cm3 · 1.2026 g/cm3(Temp: 15 °C)
Symbol(GHS)
7 · GHS07,GHS09
Signal word
Warning
Hazard statements
319 · H319-H410
Precautionary statements
264 · P264-P273-P280-P305+P351+P338-P337+P313-P391
CERCLA Reportable Quantities · 1 item

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).

Clean Water Act RequirementsToxic pollutant designated pursuant to section 307(a)(1) of the Clean Water Act and is subject to effluent limitations. /Haloethers/
Hazard Classes and Categories · 2 items

Acute Tox. 4 (50%)

Flammable agents - 2nd degree

State Drinking Water Guidelines(FL) FLORIDA 10 ug/l

Safety & protection

Fire FightingA fire in your laboratory involving this chemical should be extinguished with a dry chemical, carbon dioxide or halon extinguisher. (NTP, 1992)
First Aid · 1 item

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.

Cleanup Methods · 2 items

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/

Nonfire Spill Response · 1 item

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.

Protective Action Criteria (PAC) · 6 items

3.2 [mg/m3]

35 [mg/m3]

210 [mg/m3]

3.2 [mg/m3]

35 [mg/m3]

210 [mg/m3]

Personal Protective Equipment (PPE) · 1 item

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.

Toxicology

Environmental Fate · 4 items

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.

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Effluent ConcentrationsU.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).
Soil Adsorption/Mobility · 2 items

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.

Natural Pollution Sources4-Chlorophenyl phenyl ether is an anthropogenic compound, and is not known to exist in nature. (SRC)
Fish/Seafood Concentrations4-Chlorophenyl phenyl ether was not found in a wide variety of fish collected from fourteen Lake Michigan tributaries and embayments (detection limits not given)(1).
Artificial Pollution Sources · 1 item

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).

Environmental Biodegradation · 3 items

4-Chlorophenyl phenyl ether displayed a 62% theoretical biological oxygen demand in water (ten day test, conditions not given)(1). 4-Chlorophenyl phenyl ether was reported as undergoing 0% biodegradation in a five day test using settled domestic wastewater as an inoculum; biodegradation increased to 36% by the second subculture, and fell to 1% when using the third subculture(2,3). 4-Chlorophenyl phenyl ether was thus listed as being not significantly degraded under the conditions of the method, the lowest of a three tier rating system(3).

... The half-life of 4-chlorophenyl phenyl ether with respect to biodegradation in activated sludge is approx 4 hr.

Two water samples, taken from 2 different locations in the Tittabawassee River & spiked with the pollutant at a concn of 1 mg/l, showed 2 different rates of biodegradation. One sample exhibited no detectable degradation before 120 hr & the other, no degradation before 312 hr. Greater than 90% degradation required 264 hr in the first sample & 528 hr in the second. The experiments illustrated that biodegradation rate constants are not reproducible when microbial populations have a dissimilar history. In these 2 experiments the half-lives with respect to biodegradation would be rather meaningless since both samples exhibited lag periods (during which loss of the pollutant was undetectable) that were approx one-half of the time required for 90% degradation. Thus, it is reasonable to assume that genetic induction levels for most degradative organisms would not be reached except in the vicinity of discharge. In a non-stagnant body of surface water, a distinct microbial population would probably not be in contact with the pollutant long enough to become acclimated.

Sediment/Soil Concentrations · 1 item

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).

Environmental BioconcentrationA BCF of 736 was experimentally determined for 4-chlorophenyl phenyl ether in rainbow trout (Salmo gairdneri) (8.9 day experiment)(1).
Volatilization from Water/Soil · 1 item

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).

Environmental Abiotic Degradation · 1 item

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).

Regulatory information

CERCLA Reportable Quantities · 1 item

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).

Clean Water Act RequirementsToxic pollutant designated pursuant to section 307(a)(1) of the Clean Water Act and is subject to effluent limitations. /Haloethers/
State Drinking Water Guidelines(FL) FLORIDA 10 ug/l

Safety data

Signal word
Warning
Symbol(GHS)
GHS07,GHS09
Hazard statements
H319-H410
Precautionary statements
P264-P273-P280-P305+P351+P338-P337+P313-P391