4-ブロモジフェニルエーテル

4-Bromodiphenyl Ether

HCID 7565CAS 101-55-3

基本情報

標準SMILES
Brc1ccc(Oc2ccccc2)cc1
InChIKey
JDUYPUMQALQRCN-UHFFFAOYSA-N
分子式
C12H9BrO
平均分子量
249.1 g/mol
単同位体質量
247.98368

名称と識別子

優先名称
4-Bromodiphenyl Ether
IUPAC
1-bromo-4-phenoxybenzene
現地名
4-ブロモジフェニルエーテル
英語名
4-Bromophenoxybenzene
分子式
C12H9BrO
分子量
249.1

名称と別名

1-Bromo-4-phenoxybenzene101-55-34-Bromodiphenyl ether4-Bromophenyl phenyl ether4-Bromophenoxybenzenep-Bromodiphenyl etherBenzene, 1-bromo-4-phenoxy-p-Phenoxybromobenzenep-BromophenoxybenzeneP-BROMOPHENYL PHENYL ETHEREther, p-bromophenyl phenylPhenyl ether, 4-bromo-
名称をさらに表示
4-ブロモジフェニルエーテル4-ブロモフェニルフェニルエーテルp-ブロモジフェニルエーテル1-ブロモ-4-フェノキシベンゼン4-ブロモフェノキシベンゼン(4-ブロモフェニル)フェニルエーテルフェニル(4-ブロモフェニル)エーテルフェニル4-ブロモフェニルエーテルp-ブロモフェニルフェニルエーテル4-ブロモジフェニル エテル4-ブロモジフェニル エーテル4-ブロモジフェニルエーテル標準液ポリ臭素化ジフェニルエーテルポリブロモジフェニルエーテル4ブロモフェニルフェニルエテルブロモジフェニルエーテル4‐ブロモジフェニルエーテル標準液4-ブロモジフェニルエーテル IN ISOOCTANE4-ブロモフェニルフェニルエーテル STANDARD4-ブロモジフェニルエーテル, 50 µg/mL in Isooctanepbde 3PBDE No. 3β-NaphthyletherP-BROMDIPHENYL ETHERBDE No 3 solution4-bromo-diphenylethe4-BROMODIPHENYL OXIDE
Diphenyl ether, 4-bromo-Ether, 4-bromophenyl phenylPhenyl (4-bromophenyl) etherp-(Phenoxy)bromobenzene4-Phenoxy-1-bromobenzeneNSC 5619p-Phenoxyphenyl bromideDTXSID8023927

データベース識別子

CAS
101-55-3
PubChem CID
7565
DTXSID
DTXSID8023927
ChEMBL
CHEMBL1873236
ChEBI
CHEBI:77421
UNII
N19SE3QCFN
EC Number
202-952-4
Nikkaji
J47.554H

物性

構造計算による物性

XLogP
4.4
極性表面積
9.2 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
2
重原子数
14

実験および物理化学的性質

Density · 3 件

1.4208 at 68 °F (NTP, 1992) - Denser than water; will sink

1.6088 @ 20 °C/4 °C

1.6088 @ 20°C

Solubility · 2 件

Insol in water

> 10% in ethyl ether

Flash Pointgreater than 234 °F (NTP, 1992)
Boiling Point · 4 件

581 °F at 760 mmHg (NTP, 1992)

310.1 °C @ 760 MM HG

BP: 124-8 °C @ 3-4 mm Hg

310.1 °C @760 [mm Hg]

Melting Point · 3 件

63 °F (NTP, 1992)

18.72 °C

18.72 °C

Vapor Pressure · 3 件

0.0015 [mmHg]

0.0015 torr @ 20 °C (calc)

0.0015 [mm Hg] @20 °C

物理化学的性質

融点
18 °C · 18 °C (lit.)
沸点
305 °C · 305 °C (lit.)
比重(密度)
1.423 g/mL · 1.423 g/mL at 25 °C (lit.)
蒸気圧
1.94 x · 1.94 x 10-3 mmHg at 25 °C (subcooled liquid, Tittlemier et al., 2002)
屈折率
20 · n20/D 1.607(lit.)
闪点
230 °F · >230 °F

化学的性質

化学的特性light yellow liquid

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 14.3% (3 of 21) of reports.

Danger

H302 (28.6%): Harmful if swallowed [Warning Acute toxicity, oral];H317 (28.6%): May cause an allergic skin reaction [Warning Sensitization, Skin];H318 (28.6%): Causes serious eye damage [Danger Serious eye damage/eye irritation];H400 (66.7%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410 (33.3%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard];H411 (19%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P354+P338, P317, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 21 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 3 of 21 reports by companies.;There are 7 notifications provided by 18 of 21 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.

危険有害性情報

Regulatory Information · 5 件

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

Hazard Traits - Bioaccumulation; Environmental Persistence; Environmental tox;Authoritative List - CWA 303(c); CWA 303(d); US EPA NWMP PBTs;Report - if used as a fragrance or flavor ingredient

S - indicates a substance that is identified in a final Significant New Use Rule.

Status: Active Update: 15-07-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/32702

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.)

DOT LabelClass 9
Fire HazardsCombustible. (NTP, 1992)
Health Hazards · 1 件

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:;Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or asphyxiation. Runoff from fire control or dilution water may cause environmental contamination. (ERG, 2024)

Hazards SummaryMay form unstable pyrophoric peroxides on exposure to air; [CAMEO]See Decabromodiphenyl ether.
Reactive GroupEthers;Aryl Halides

安全と保護具

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 件

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)

Cleanup MethodsAdsorption capacities of activated carbon for /wastewater pollutants/: 4-bromophenyl phenyl ether 144 mg/g. /From table/
Nonfire Spill Response · 1 件

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 material from exposure to light, and store it in a refrigerator. (NTP, 1992)

Disposal Methods · 2 件

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U030, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids. A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds.

Isolation and Evacuation · 1 件

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:;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 the immediate precautionary measure distance, in the downwind direction, as necessary.;FIRE: If tank, rail tank car or highway tank 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, 2024)

毒性情報

Treatment · 1 件

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Health EffectsPolybrominated diphenyl ethers may affect the thyroid gland and liver. Animals studies have also shown that PDBEs can cause neurobehavioral alterations and affect the immune system. (L628)
Ecotoxicity Values · 5 件

LC50 Lepomis macrochirus (bluegill) 51 mg/l/24 hr, age young, wt 0.32-1.2 g, static bioassay, total hardness of water 32-48 mg/l CaCO3, total alkalinity 28-34 mg/l CaCO3, pH 6.7-7.8, dissolved oxygen concn 7.0-8.8 mg/l, temp 22 + or - °C /Sample purity > 80%/

LC50 Lepomis macrochirus (bluegill) 5.9 mg/l/98 hr, age young, wt 0.32-1.2 g, static bioassay, total hardness of water 32-48 mg/l CaCO3, total alkalinity 28-34 mg/l CaCO3, pH 6.7-7.8, dissolved oxygen concn 7.0-8.8 mg/l, temp 22 + or - °C /Sample purity > 80%/

LC50 Daphnia magna (Water flea) 0.46/mg/l/24 hr. /Conditions of bioassay not specified/

LC50 Daphnia magna (Water flea) 0.36 mg/l/48 hr. /Conditions of bioassay not specified/

For more Ecotoxicity Values (Complete) data for P-BROMOPHENYL PHENYL ETHER (8 total), please visit the HSDB record page.

Environmental Fate · 5 件

AQUATIC FATE: No information was found in the reviewed literature that would indicate hydrolysis as an aquatic fate for this cmpd. It is ... considered to be unlikely that any of the covalent bonds of 4-bromophenyl phenyl ether will hydrolyze at ambient environmental conditions, since the negative charge-density of the aromatic ring will impede the nucleophilic attack of water or hydroxide ion.

AQUATIC FATE: No information was found in the reviewed literature that would support any role for oxidn of this cmpd as an aquatic fate. Indirect photolysis involving interaction of hydroxyl radical with the aromatic ring, is considered to be too slow in water to be environmentally significant for this cmpd. It is at present uncertain how much of this pollutant will volatilize into the atmosphere from surface waters. Any 4-bromophenyl phenyl ether that enters into the troposphere will be subject to photodegradation and reprecipitation with rain. The /proposed/ atmospheric half-life of unsubstituted benzene ... is 2.4 to 24 hr. ... A halogen substituent on an aromatic ring should decrease its susceptibility to photodegradation in the troposphere. Although the electron donating resonance effect of an oxygen substituent should facilitate destruction, it is uncertain how the presence of both groups will affect the atmospheric destruction of 4-bromophenyl phenyl ether.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4200(SRC), determined from a structure estimation method(2), indicates that 4-bromophenyl phenyl ether is expected to have slight mobility in soil(SRC). Volatilization of 4-bromophenyl phenyl ether from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). 4-Bromophenyl phenyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.0012 mm Hg(SRC), determined from a fragment constant method(4). No data are available pertaining to chemical degradation processes for 4-bromophenyl phenyl ether in soil. A single biodegradation study suggests that 4-bromophenyl phenyl ether is resistant to biodegradation(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4200(SRC), determined from a structure estimation method(2), indicates that 4-bromophenyl phenyl ether is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.2X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 16 hours and 10 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 1300(SRC), from an estimated log Kow of 4.9(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is very high. A single biodegradation study suggests that 4-bromophenyl phenyl ether is resistant to biodegradation(8). Aquatic hydrolysis and oxidation (via singlet oxygen and peroxy radicals) are not important(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-bromophenyl phenyl ether, which has an estimated vapor pressure of 1.5X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 4-bromophenyl phenyl 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 5.1X10-12 cu cm/molecule-sec at 25 °C(SRC), determined using a structure estimation method(3).

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.
Exposure RoutesOral (L628) ; inhalation (L628) ; dermal (L628)

法規制情報

Regulatory Information · 5 件

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

Hazard Traits - Bioaccumulation; Environmental Persistence; Environmental tox;Authoritative List - CWA 303(c); CWA 303(d); US EPA NWMP PBTs;Report - if used as a fragrance or flavor ingredient

S - indicates a substance that is identified in a final Significant New Use Rule.

Status: Active Update: 15-07-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/32702

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.)

RCRA Requirements · 1 件

U030; As stipulated in 40 CFR 261.33, when 4-bromophenyl phenyl ether, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

CERCLA Reportable Quantities · 1 件

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 100 lb or 45.4 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 Federal Water Pollution Control Act and is subject to effluent limitations. /Haloethers/
State Drinking Water Guidelines(FL) FLORIDA 10 ug/l

安全データ

wgk
3
tsca
TSCA listed
ridadr
UN 3082 9/PG 3
毒性
LC50 (24-h) for Daphnia magna 0.46 mg/L (LeBlanc, 1980).
hs_code
29093090
risk_code
50/53-67-65-38-11-43-41-22

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

Polybrominated biphenyls can be absorbed through oral, inhalation, and dermal routes. Once in the body they distribute throughout and bioaccumulate in the blood, breast milk, and adipose tissue. The extent of PBDE metabolism depends on the degree of bromination. Metabolism is believed to involve debromination and methylation, resulting in phenolic metabolites. Metabolized and unmetabolized PDBE compounds are excreted mainly in the faeces. (L628, L881)

用途と製造

Uses · 4 件

Used formerly as additive flame retardant for polymers; Not commercially produced in the US; [HSDB]

RESEARCH CHEMICAL

Used as flame retardant additives in polymers. /Former use/

Polybrominated diphenyl ethers (PBDEs) are flame-retardant chemicals found in plastics used in a variety of consumer products to make them difficult to burn. Because they are mixed into plastics and foams rather than bound to them, PBDEs can leave the products that contain them and enter the environment. (L628)

U.S. Production · 2 件

(1977) NOT PRODUCED COMMERCIALLY IN THE USA

(1979) NOT PRODUCED COMMERCIALLY IN THE USA

Methods of ManufacturingSOME HALOGENATED DIPHENYL ETHERS CAN BE PREPARED BY DIRECT HALOGENATION OF DIPHENYL ETHER CATALYZED BY LEWIS ACIDS & BY DEAMINATION OF NITRO- & AMINO-SUBSTITUTED DIPHENYL ETHERS. /HALOGENATED DIPHENYL ETHERS/
General Manufacturing Information · 2 件

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

NOT PRODUCED COMMERCIALLY IN THE USA

応用分野

一般的な説明Liquid. Freezing point 18°C. Density 1.423 g / cm3. Insoluble or slightly soluble in water.

補足説明

定義ChEBI: An aromatic ether that is diphenyl ether substituted at position 4 by a bromo group.

関連反応

20 件

関連ノート

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