Diphenyl Ether

HCID 7583CAS 101-84-8

Basic information

Standard SMILES
c1ccc(Oc2ccccc2)cc1
InChIKey
USIUVYZYUHIAEV-UHFFFAOYSA-N
Molecular formula
C12H10O
Average molar mass
170.21 g/mol
Monoisotopic mass
170.07316494

Names & identifiers

Preferred name
Diphenyl Ether
IUPAC
phenoxybenzene
English name
Diphenyl ether
Molecular formula
C12H10O
Molecular weight
170.21

Names & synonyms

DIPHENYL ETHERDiphenyl oxide101-84-8PhenoxybenzenePhenyl etherBenzene, 1,1'-oxybis-DiphenyletherOxybisbenzenePhenyl oxideBiphenyl oxideGeranium crystalsOxydiphenyl
Show more names
OxydibenzeneFEMA 3667Diphenyl etheether,diphenylDEPHENYL OXIDE
Chemcryl JK-EBBenzene, phenoxy-1,1'-Oxybis(benzene)1,1'-OxybisbenzeneEther, diphenylFEMA No. 3667DTXSID90218473O695R5M1U

Database identifiers

CAS
101-84-8、32576-61-7
PubChem CID
7583
DTXSID
DTXSID9021847
ChEMBL
CHEMBL38934
ChEBI
CHEBI:39258
UNII
3O695R5M1U
EC Number
202-981-2
Nikkaji
J3.598J

Properties

Computed structural properties

XLogP
4.2
Topological polar surface area
9.2 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
13

Experimental & physicochemical properties

LogP · 3 items

log Kow = 4.21

4.21

4.21

OdorGeranium-like odor
Density · 6 items

1.07 at 80.6 °F (USCG, 1999) - Denser than water; will sink

1.0661 g/cu cm at 30 °C

Percent in saturated air: 0.0028; Density of saturated air: 1.0014 (Air = 1)

Relative density (water = 1): 1.08

1.071-1.075

1.08

Viscosity3.4909X10-3 Pa-sec at melting point
Color/Form · 2 items

Colorless crystals or liquid

Colorless, crystalline solid or liquid (above 82 degrees F)

Solubility · 6 items

Insoluble (NTP, 1992)

In water, 18 mg/L at 25 °C

Soluble in ethanol, ether, benzene, acetic acid; slightly soluble in chloroform

0.018 mg/mL at 25 °C

Solubility in water, g/100ml: 0.002 (very poor)

Insoluble in water, soluble in oils

Physicochemical properties

Melting point
26 °C · 26 °C
Boiling point
259 °C · 259 °C(lit.)
Density
1.073 g/mL · 1.073 g/mL at 25 °C(lit.)
vapor density
5.86 · >5.86 (25 °C, vs air)
vapor pressure
1 mm · <1 mm Hg ( 20 °C)
refractive index
20 · n20/D 1.579(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 0.5% (12 of 2199) of reports.

Warning

H319 (84.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H400 (16.1%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410 (10.3%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard];H411 (78.8%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P264+P265, P273, P280, P305+P351+P338, P337+P317, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2199 reports by companies from 45 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 12 of 2199 reports by companies.;There are 44 notifications provided by 2187 of 2199 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 5 items

Chemical: Benzene, 1,1'-oxybis-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Benzene, 1,1'-oxybis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1,1'-oxybis- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 04-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/14971;Status: Active Update: 07-10-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/18130

Diphenyl ether: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelClass 9
Fire Hazards · 2 items

This chemical is combustible. (NTP, 1992)

Combustible.

Fire PotentialCombustible when exposed to heat or flame.
Health HazardsInhalation may cause nausea because of disagreeable odor. Contact of liquid with eyes causes mild irritation. Prolonged exposure of skin to liquid causes reddening and irritation. Ingestion produces nausea. (USCG, 1999)
Hazards Summary · 1 item

. . . industrial experience has shown no evidence that phenyl ether, either as liquid mist or vapor, was a human health hazard under ordinary conditions of manufacture, handling, or use. Controlling workplace concentration below 1 ppm has been recommended to prevent the disagreeable odor and nausea in some workers. Damage to the liver and other organs has been documented in acute feeding studies of experimental animals; LD50 = 4 g/kg for rats and guinea pigs; [ACGIH] An irritant of the eyes and respiratory tract; [ICSC]

Safety & protection

Fire Fighting · 2 items

Fire Extinguishing Agents Not to Be Used: Water or foam may cause frothing.;Fire Extinguishing Agents: Dry chemical, carbon dioxide (USCG, 1999)

Use water spray, powder, foam, carbon dioxide.

First Aid Measures · 4 items

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

Rinse mouth.

First Aid · 2 items

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)

(General first aid procedures);Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.;Skin: Soap wash promptly - If this chemical contacts the skin, promptly wash the contaminated skin with soap and water. If this chemical penetrates the clothing, promptly remove the clothing and wash the skin with soap and water. Get medical attention promptly.;Breathing: Respiratory support

Safe StorageSeparated from strong oxidants. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.
Exposure Control and Personal Protection1.0 [ppm]
Fire Fighting Procedures · 4 items

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

If material involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible.

Dry chemical, carbon dioxide. Water or foam may cause frothing.

Toxicology

Body BurdenAs part of the USEPA's National Human Adipose Tissue Survey (NHATS), diphenyl ether was detected in 40 of 44 composite adipose tissue collected for fiscal year 1982(1).
Target OrgansEyes, skin, respiratory system
Ecotoxicity Values · 5 items

LC50; Species: Daphnia magna (Water Flea) age < or =24 hr; Conditions: freshwater, static, 22 °C, pH 7.4-9.4, dissolved oxygen 6.5-9.1 mg/L; Concentration: 1400 ug/L for 24 hr (95% confidence limit: 1100-1900 ug/L) /> or =80% purity/

LC50; Species: Daphnia magna (Water Flea) age < or =24 hr; Conditions: freshwater, static, 22 °C, pH 7.4-9.4, dissolved oxygen 6.5-9.1 mg/L; Concentration: 670 ug/L for 48 hr (95% confidence limit: 110-1100 ug/L) /> or =80% purity/

LC50; Species: Cyprinodon variegatus (Sheepshead Minnow) age 14-28 dph, juvenile, length 8-15 mm; Conditions: saltwater, static; Concentration: 2400 ug/L for 24 hr (95% confidence limit: 1800-3200 ug/L) /> or =80% purity/

LC50; Species: Cyprinodon variegatus (Sheepshead Minnow) age 14-28 dph, juvenile, length 8-15 mm; Conditions: saltwater, static; Concentration: 2400 ug/L for 48 hr (95% confidence limit: 1800-3200 ug/L) /> or =80% purity/

For more Ecotoxicity Values (Complete) data for DIPHENYL ETHER (6 total), please visit the HSDB record page.

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 1950(2), indicates that diphenyl ether is expected to have low mobility in soil(SRC). Volatilization of diphenyl ether from moist soil surfaces may be an important fate process(SRC) given its Henry's Law constant estimated as 2.8X10-4 atm-cu m/mole(SRC) based upon its vapor pressure, 2.25X10-2 mm Hg(3), and water solubility, 18 mg/L(4). Diphenyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.25X10-2 mm Hg at 25 °C(3). A 6.3% of theoretical BOD using activated sludge in the Japanese MITI test(5) suggests that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 1950(2), indicates that diphenyl ether is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces may be expected(3) based upon an estimated Henry's Law constant of 2.8X10-4 atm-cu m/mole(SRC) derived from its vapor pressure, 2.25X10-2 mm Hg(4), and water solubility, 18 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4 hours and 6 days, respectively(SRC). According to a classification scheme(6), experimental BCF values of 195, 470 and 590, suggest that bioconcentration in aquatic organisms is moderate to high(SRC). A 6.3% of theoretical BOD using activated sludge in the Japanese MITI test(5) suggests that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diphenyl ether, which has a vapor pressure of 2.25X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diphenyl ether 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 days(SRC), calculated from its rate constant of 9.8X10-12 cu cm/molecule-sec at 25 °C(3). Diphenyl ether contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Food Survey ValuesDiphenyl ether has been qualitatively detected in the volatile aroma components of roasted beef(1).
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.

Regulatory information

Regulatory Information · 5 items

Chemical: Benzene, 1,1'-oxybis-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Benzene, 1,1'-oxybis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1,1'-oxybis- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 04-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/14971;Status: Active Update: 07-10-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/18130

Diphenyl ether: Does not have an individual approval but may be used under an appropriate group standard

TSCA Requirements · 1 item

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Diphenyl oxide is included on this list. Effective date: 4/13/89; Sunset date: 6/30/98.

Atmospheric Standards · 1 item

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Diphenyl oxide is produced, as an intermediate or a final product, by process units covered under this subpart.

Safety data

OEB
B
OEL
TWA: 1 ppm (7 mg/m3)
PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
2
IDLA
100 ppm
tsca
TSCA listed

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 4 items

... In the rabbit no cleavage of the ether linkage /of phenyl ether/ occurs. The major metabolite was the p-hydroxylated ether, which is excreted both unconjugated (15%) and conjugated with glucuronic acid (63%) and sulfuric acid (12%). Another metabolite was also isolated from the rabbit urine and fairly well identified as di(p-hydroxyphenyl) ether.

Subcellular fractions of trout liver homogenate metab diphenyl ether mainly to 4 hydroxy derivates with traces of other compounds including 3 hydroxy derivates and possibly 4,4'-dihydroxy derivates.

The bacterium Sphingomonas sp strain SS3, which utilizes diphenyl ether as source of carbon and energy, was enriched from soil samples of an industrial waste deposit. During diphenyl ether degradation in batch culture experiments, phenol and catechol were produced as intermediates which were then channeled into the 3-oxoadipate pathway. The initial step in the degradation follows the recently discovered mechanism of 1,2-dioxygenation, which yields unstable phenolic hemiacetals from diphenyl ether structures.

Screening of selected fungi proved Cunninghamella echinulata most suitable for research on hydroxylation of biphenyl oxide. The process depended on cultivation conditions and yielded up to 76% 4-hydroxybiphenyl oxide and about 6% 4,4'-dihydroxybiphenyl oxide.

Absorption, Distribution and Excretion · 3 items

The absorption of diphenyl ether after oral uptake is up to 90% in rats and rabbits and is independent of the administered dose. The data on dermal absorption are somewhat conflicting. After semi-occlusive application of 10-1,000 mg/kg to the clipped skin of rats, almost 20% of the dose was absorbed as measured by the amount excreted in urine. However, in a diffusion experiment only 0.3% (rat skin) or 0.2% (human skin) of diphenyl ether penetrated the skin in vitro. The higher absorption in the in vivo experiment may have been caused by the vehicle (diethyl phthalate) and some oral uptake after removal of the occlusion plaster.

After intraperitoneal injection in rats, diphenyl ether was distributed into all organs and tissues within 1 hour with maximum concentrations in liver, lung, kidney and spleen.

... Phenyl ether, when injected into the rabbit, was excreted in the urine as p-hydroxyphenyl phenyl ether and none was excreted as the unchanged ether. /Route not specified/

Cellular LocationsMembrane

Uses & manufacturing

Uses · 6 items

Used as a heat transfer medium, Dowtherm A, and as a chemical intermediate for surface active agents and lubricants; [ACGIH]

Perfumery, particularly soaps; heat-transfer medium resins for laminated electrical insulation; chemical intermediate for such reactions as halogenation, acylation, alkylation.

Commonly used dye carrier. /From table/

... Employed as a processing aid in the production of polyesters; several polybromine derivatives of diphenyl ether are used as fire retardants.

... Used in large quantities in soap perfumes. However, its main application is as a heat-transfer medium (eutectic mixture with diphenyl).

For more Uses (Complete) data for DIPHENYL ETHER (6 total), please visit the HSDB record page.

U.S. Imports · 3 items

(1972) 2.74X10+6 G

(1975) 9.17X10+7 G

581,836 lbs (principal US custom districts)

U.S. Production · 6 items

2023: 40,000,000 - <55,000,000 lb;2022: 70,000,000 - <85,000,000 lb;2021: 70,000,000 - <85,000,000 lb;2020: 70,000,000 - <85,000,000 lb

(1972) OVER 4.54X10+5 G

(1975) PROBABLY GREATER THAN 4.54X10+5 G

Benzene, 1,1'-oxybis- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Benzene, 1,1'-oxybis-. Aggregated National Production Volume: 50 to < 100 million pounds.

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Benzene, 1,1'-oxybis-. National Production Volume: 77,839,277 lb/yr.

Consumption PatternsApproximately 67% is used in making heat-transfer fluids; approximately 100,000 lbs used annually in fragrance products
Consumer UsesNot Known or Reasonably Ascertainable;Fragrance
Industry UsesIntermediate;Fragrance;Heat transferring agent;Processing aids not otherwise specified;Surfactant (surface active agent)
Applications · 6 items

DescriptionDiphenyl ether (diphenyl oxide) is a colorless liquid with a floral odor. It is a white, crystalline solid at temperatures below 80ºF (27ºC). It has low volatility, low solubility in water, and is stable at high temperatures. Avoid contact with oxidizing materials. Liquid diphenyl oxide is used primarily in industry. It is used in the industrial setting as a heat transfer fluid. It is the major component of Dowtherm A® (an eutectic mixture of phenyl ether and biphenyl) and further as a chemical intermediate in the production of surface-active agents and hightemperature lubricants, and in perfumery due to its geranium-like odour (ACG99b). It is also used as a chemical intermediate in the manufacture of surfactants and fire retardants. Diphenyl oxide (DPO) is manufactured using the direct phenol method.

OccurrenceReported found in muscat grapes, grilled beef, green tea, potato chips, buckwheat, Bourbon vanilla and lemon balm.

UsesDiphenyl ether is widely used as a heat transfer agent and a dye carrier. It can be used alone or as a mixture with other materials. Because of its reactivity, It can also be used as a raw material or chemical intermediate to produce commercial products. Diphenyl ether is used in the production of: Diphenyl ether is employed as a processing aid in the production of polyesters. It acts as a chemical intermediate in the production of surface active agents and high temperature lubricants, fire retardants like polybrominated diphenyl ethers (PBDEs) and fragrance for detergents. Heat transfer media – like DOWTHERMTM fluids used for heating industrial processes Alkylated diphenyl oxides – used to make surfactants, greases and lubricants Halogenated diphenyl oxides – used in insecticides, wood preservatives, and flame retardants for appliance casings in consumer electronic products High temperature solvents Coatings Textile dye labeling Plastics – like ethylene-propylene-diene monomer (EPDM) rubber that is used for membrane roofing materials Diphenyl ether plays a vital role in the Ferrario reaction to produce phenoxathiin, which finds application in polyamide and polyimide production. Involving similar reactions, diphenyl ether is a significant side product in the high-pressure hydrolysis of chlorobenzene in the production of phenol. Diphenyl ether is found in alcoholic beverages. Diphenyl ether is present in muscat grapes, green tea, vanilla, lemon balm, buckwheat, potato chips and grilled beef. Diphenyl ether is a flavouring ingredient.

UsesPhenyl Ether is an Impurity of Propofol (P829750).

General DescriptionDiphenyl ether occurs, e.g., in lemon balm oil. The compound forms colorless crystals that possess a geranium-like aroma. Diphenyl ether is formed as a byproduct in the high-pressure hydrolysis of chlorobenzene. Because of its high thermal stability, a eutectic mixture of diphenyl ether and biphenyl is employed as a heat transfer medium. Diphenyl ether is the starting material for organic intermediates and is used as a fragrance component. The compound is also employed as a processing aid in the production of polyesters; several polybromine derivatives of diphenyl ether are used as fire retardants.

General DescriptionColorless liquid with a mild pleasant odor. May float or sink in water. Freezing point is 81°F.

Preparation methods

PreparationBy heating potassium phenolate with bromobenzene or with chlorobenzene at elevated temperatures.

Upstream & downstream products

Downstream products

Additional notes

DefinitionChEBI: Diphenyl ether is an aromatic ether in which the oxygen is attached to two phenyl substituents. It has been found in muscat grapes and vanilla. It has a role as a plant metabolite.

Related reactions

1,226 records

Linked notes

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