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4-フェニルフェノール

4-Hydroxybiphenyl

HCID 7103
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印刷プレビュー
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
1322-20-9
標準SMILES
Oc1ccc(-c2ccccc2)cc1
InChIKey
YXVFYQXJAXKLAK-UHFFFAOYSA-N
分子式
C12H10O
平均分子量
170.21 g/mol
単同位体質量
170.07316494

概要

Biphenyl-4-ol is a member of the class of hydroxybiphenyls that is biphenyl carrying a hydroxy group at position 4.

名称と識別子

優先名称
4-Hydroxybiphenyl
IUPAC
4-phenylphenol
現地名
4-フェニルフェノール
英語名
4-Phenylphenol
分子式
C12H10O
分子量
170.21

名称と別名

4-Phenylphenol92-69-3[1,1'-Biphenyl]-4-ol4-HYDROXYBIPHENYLBiphenyl-4-olp-Phenylphenol4-Biphenylolp-Hydroxybiphenylp-Hydroxydiphenyl4-HydroxydiphenylParaxenolp-Biphenylol
名称をさらに表示
4-フェニルフェノール4-フェニルフェノール標準品P-ヒドロキシビフェニルP-フェニルフェノール[1,1’ビフェニル]4オルフェニルフェノール4‐フェニルフェノール4‐フェニルフェノール標準品4-ヒドロキシビフェニルビフェニル-4-オール4-ヒドロキシフェニル4-ヒドロキシ-1,1′-ビフェニルパラキセノール4-ビフェニルオール[1,1'-ビフェニル]-4-オール4-ヒドロキシ[1,1′-ビフェニル]1,1′-ビフェニル-4-オール[1,1′-ビフェニル]-4-オール4-ヒドロキシジフェニル4-pp(1,1’-Biphenyl)-4-olp-Xenol
4-Diphenylolpara-Phenylphenolpara-HydroxydiphenylTetrasin P 300Tetrosin P 300Biphenyl, 4-hydroxy-(1,1'-Biphenyl)-4-olDTXSID7021152

データベース識別子

CAS
1322-20-9、92-69-3
PubChem CID
7103
DTXSID
DTXSID7021152
ChEMBL
CHEMBL73380
ChEBI
CHEBI:34422
UNII
50LH4BZ6MD
EC Number
202-179-2、215-333-9
Nikkaji
J3.561K

物性

構造計算による物性

XLogP
3.2
極性表面積
20.2 Ų
水素結合供与体数
1
水素結合受容体数
1
回転可能結合数
1
重原子数
13
形式電荷
0
複雑度
141

実験および物理化学的性質

Chemical ClassesOther Classes -> Other Aromatic Compounds
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP · 2 件

Log Kow = 3.20

3.33

Density · 2 件

1.27 kg/l @ 25 °C

1.27 @25 °C

Color/Form · 3 件

NEARLY WHITE CRYSTALS

NEEDLES OR PLATES FROM DILUTE ALCOHOL

White flakes

Solubility · 4 件

SLIGHTLY SOL IN PETROLEUM ETHER; VERY SOL IN ALCOHOL, ETHER, CHLOROFORM & PYRIMIDINE

SOL IN ALCOHOL, ALSO IN ALKALIES & MOST ORGANIC SOLVENTS; INSOLUBLE IN WATER

Soluble in oxygenated solvents.

Water solubility = 56.2 mg/l

Flash Point · 2 件

165.5 °C

330 °F

Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point305-308 °C
Melting Point164-165 °C

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Warning

H315 (98.4%): Causes skin irritation [Warning Skin corrosion/irritation]

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

Aggregated GHS information provided per 124 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 4 件

Chemical: [1,1'-Biphenyl]-4-ol

[1,1'-Biphenyl]-4-ol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of [1,1'-Biphenyl]-4-ol 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: Cease Manufacture Update: 29-05-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/11340

[1,1'-Biphenyl]-4-ol: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryA tumorigen; Intraperitoneal LD50 (mouse) = 150 mg/kg; [RTECS] Emergency treatment: see Biphenyl. [HSDB] An irritant; [MSDSonline] See Biphenyl.
TSCA Requirements · 1 件

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. (1,1'-Biphenyl)-4-ol is included on this list.

Hazard Classes and CategoriesSkin Irrit. 2 (98.4%)

安全と保護具

化学と産業

薬理情報

Mechanism of Action · 1 件

The cytotoxic effects of biphenyl (BP) and its hydroxylated derivatives, o-phenylphenol (OPP), m-phenylphenol (MPP) and p-phenylphenol PPP) ... were investigated in freshly isolated rat hepatocytes. OPP, MPP and PPP, at concn of 0.75 mM, resulted in the loss of intracellular ATP, glutathione (GSH) and protein thiols, causing cell death. OPP epoxide and BP were less toxic than the OPP isomers. MPP or PPP compared with OPP caused serious impairments in oxidative phosphorylation in mitochondria isolated from rat liver. ... These results indicate that the addition of a hydroxyl group to the aromatic ring of BP enhances BP induced cytotoxicity and that the mitochondria are a common target of OPP isomers and other BP derivatives. In addition, the para- or meta-hydroxyl groups rather than the ortho-hyroxyl group incr the toxicity. ...

Metabolism/Metabolites · 6 件

RAT OR RABBIT LIVER HOMOGENATE OR MICROSOMES FORMED AS THE ONLY METABOLITE 4-HYDROXYBIPHENYL. THIS WAS ALSO THE ONLY SIGINIFICANT BIPHENYL METABOLITE IN ACID-HYDROLYZED RATS URINE.

BIPHENYL 2- & 4-HYDROXYLASE ACTIVITIES & CYTOCHROME P450 CONCN IN MICROSOMES WERE INCR BY ORAL DOSES OF LESS THAN 1 UG TCDD (2,3,7,8-TETRACHLORODIBENZO-P-DIOXIN, A CONTAMINANT OF HERBICIDE 2,4,5-T)/KG.

THE ORDER OF PREFERENCE FOR POSITION OF HYDROXYLATION OF BIPHENYL BY LIVER MICROSOMES OF RATS, RABBITS, & GUINEA PIGS WAS 4-, 3-, 2-. AFTER FEEDING BIPHENYL TO RABBITS & MICE, GLUCURONIDES OF HYDROXYLATED METABOLITES WERE FOUND IN THE URINE.

4-HYDROXYBIPHENYL & 2-HYDROXYBIPHENYL CAN EXIST IN NATURE AS FUNGAL METABOLITES OF BIPHENYL.

For more Metabolism/Metabolites (Complete) data for 4-HYDROXYBIPHENYL (14 total), please visit the HSDB record page.

4-Phenylphenol has known human metabolites that include (2S,3S,4S,5R)-3,4,5-Trihydroxy-6-(4-phenylphenoxy)oxane-2-carboxylic acid.

用途と製造

Uses · 6 件

Used in rubber chemicals, fungicides, and in the production of dyes, varnish resins, and nonionogenic emulsifiers; [HSDB]

Farming (Pesticides) [Category: Industry]

AS INTERMEDIATE IN MFR OF RESINS; ALSO IN RUBBER INDUSTRY

INTERMEDIATE FOR DYES AND RESINS; RUBBER CHEMICALS; LABORATORY REAGENT; FUNGICIDE

関連反応

271 件
反応記録を作成
HRID 14592 の反応式
HRID 14592反応物としてuspto-grants-2010_06
HRID 16283 の反応式
HRID 16283反応物としてuspto-grants-2010_06
HRID 17729 の反応式
HRID 17729反応物としてuspto-grants-2010_06
HRID 64693 の反応式
HRID 64693反応物としてuspto-grants-1986_09
HRID 101740 の反応式
HRID 101740反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 108810 の反応式
HRID 108810反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 116514 の反応式
HRID 116514反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 119250 の反応式
HRID 119250反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
1 / 34 ページ

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す
Vapor Pressure0.0000188 [mmHg]
Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR

物理化学的性質

融点
164 · 164-166 °C (lit.)
沸点
321 °C · 321 °C (lit.)
比重(密度)
1.0149 · 1.0149 (rough estimate)
蒸気圧
0 Pa · 0Pa at 25℃
屈折率
1.6188 · 1.6188 (estimate)
闪点
330 °F · 330 °F
貯蔵温度
Sealed in dry,Room Temperature
溶解性
50 mg/mL · メタノール:可溶50mg/mL 無色透明
外見
フレーク
酸解離定数(Pka)
9.55 · 9.55(at 25℃)
色
白色~やや黄色
PH
7 · 7 (0.7g/l, H2O, 20℃)
水溶解度
0.7 g/L · 0.7g/L(20℃)
Merck
14 · 14,7305
BRN
1907452 · 1907452
Henry's Law Constant
1.6 · 1.6×10-1 mol/(m3Pa) at 25℃, Mackay et al. (2006)
安定性
安定。強酸化剤、強塩基、ハロゲンとは相容れない。可燃性。
InChI
1S/C12H10O/c13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9,13H
InChIKey
YXVFYQXJAXKLAK-UHFFFAOYSA-N
SMILES
Oc1ccc(cc1)-c2ccccc2
LogP
3.6 at · 3.6 at 25℃
CAS データベース
92 · 92-69-3(CAS DataBase Reference)
NISTの化学物質情報
p-Hydroxybiphenyl(92-69-3)
EPAの化学物質情報
4 · 4-Phenylphenol (92-69-3)

化学的性質

化学的特性light tan solid (odour threshold detection limit 0.7 ppm)

Disposal Methods · 1 件

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Protective Action Criteria (PAC) · 3 件

0.49 [mg/m3]

5.4 [mg/m3]

32 [mg/m3]

毒性情報

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 1300(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that 4-hydroxybiphenyl will have low mobility in soil(SRC). Based on limited data, 4-hydroxybiphenyl may be resistant to biodegradation under aerobic conditions(SRC). 4-Hydroxybiphenyl at 30 mg/L was inoculated with activated sludge; over 4 weeks, 0% of the theoretical BOD was obtained(4). A pure Pseudomonas culture, however, was able to utilize 4-hydroxybiphenyl as a sole carbon source(5). 4-Hydroxybiphenyl's values for vapor pressure(6) and Henry's Law constant(7,SRC) indicate that volatilization from dry and moist soil surfaces is not likely to be a major fate process for this compound(SRC).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 1300(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that 4-hydroxybiphenyl may adsorb to suspended solids and sediment(SRC) in the water column. Based on limited data, 4-hydroxybiphenyl may be resistant to biodegradation under aerobic conditions(SRC). 4-Hydroxybiphenyl at 30 mg/l was inoculated with activated sludge; over 4 weeks, 0% of the theoretical BOD was obtained(4). A pure Pseudomonas culture, however, was able to utilize 4-hydroxybiphenyl as a sole carbon source(5). 4-Hydroxybiphenyl is not expected to volatilize from water surfaces based on an estimated Henry's Law constant of 5.2X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(6). BCF values of 30-57, measured in orange-red killifish(4), suggest that 4-hydroxybiphenyl will bioconcentrate in aquatic organisms(SRC).

ATMOSPHERIC FATE: According to a suggested classification scheme(1), an estimated vapor pressure of 1.8X10-5 mm Hg at 25 °C(2,SRC) indicates that 4-hydroxybiphenyl will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 4-hydroxybiphenyl 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 about 6 hours(3,SRC). Particulate-phase 4-hydroxybiphenyl may be physically removed from the air by wet and dry deposition(SRC).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Effluent Concentrations4-Hydroxybiphenyl was measured in a standard reference diesel particulate sample (NBS 1650) at unreported concentrations(1).
Soil Adsorption/Mobility · 1 件

The Koc of 4-hydroxybiphenyl is estimated as approximately 1300(SRC), using a measured log Kow of 3.20(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that 4-hydroxybiphenyl has low mobility in soil(SRC).

Natural Pollution Sources4-Hydroxybiphenyl is formed as a reaction product from the photolysis of 4-chlorobiphenol in water(1).
Human Toxicity ExcerptsMODERATELY TOXIC BY INGESTION.
Artificial Pollution Sources4-Hydroxybiphenyl's production and use in the manufacture of dyes and resins, rubber chemicals, fungicide(1) and nonionogenic emulsifiers(2) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 件

4-Hydroxybiphenyl at 30 mg/L was inoculated with activated sludge; over 4 weeks, 0% of the theoretical BOD was obtained(1), indicating that this compound is resistant to biodegradation in this system(SRC). A Pseudomonas strain, isolated by enrichment culture from activated sludge, was able to utilize 4-hydroxybiphewnyl as the sole carbon source(2) while a pure Alcaligenes culture, isolated from soil, was not(4).

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Environmental Bioconcentration · 1 件

Measured BCF values of 30-48 and 39-57 were determined in orange-red killifish following a 48 hour exposure period to 2 and 20 ug/L 4-hydroxybiphenyl, respectively(1). According to a recommended classification scheme(2), these BCF values suggest that bioconcentration in aquatic organisms is moderate, not high(SRC).

Volatilization from Water/Soil · 1 件

The Henry's Law constant for 4-hydroxybiphenyl is estimated as 5.2X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that 4-hydroxybiphenyl will be essentially nonvolatile from water surfaces(2,SRC). 4-Hydroxybiphenyl's values for vapor pressure(3) and Henry's Law constant(1,SRC) indicate that volatilization from dry and moist soil surfaces is not likely to be a major fate process for this compound(SRC).

Non-Human Toxicity Excerpts · 5 件

IN RATS, 2-HYDROXYBIPHENYL HAD A GREATER INDUCING EFFECT ON THE ACTIVITY OF ANILINE HYDROXYLASE & AMINOPYRINE N-DEMETHYLASE THAN DID 4-HYDROXYBIPHENYL.

4-HYDROXYBIPHENYL & 2-HYDROXYBIPHENYL WERE TOXIC IN VITRO TO PTYCHODISCUS BREVIS, WITH THE 4-HYDROXY DERIVATIVE BEING SLIGHTLY MORE EFFECTIVE IN INDUCING LYSIS OF THE RED TIDE ORGANISM.

IN VITRO METAB OF P-NITROANISOLE, AMINOPYRINE & ANILINE BY RAT LIVER MICROSOMAL MONOXYGENASES WERE STUDIED, 4-OH-BIPHENYL CAUSED COMPETITIVE INHIBITION OF AMINOPYRINE DEMETHYLATION & ANILINE HYDROXYLATION BUT FAILED TO INHIBIT P-NITROANISOLE METAB BY NORMAL MICROSOMES.

MUTAGENICITY OF DIPHENYL & ITS 15 DERIV WAS EXAM BY MEANS OF DNA REPAIR TEST WITH E COLI WP2, WP2 UVRA, CM571 & WP100 & REVERSION TEST WITH S TYPHIMURIUM TA98 & TA100. P-PHENYL-PHENOL WAS NONMUTAGENIC.

For more Non-Human Toxicity Excerpts (Complete) data for 4-HYDROXYBIPHENYL (6 total), please visit the HSDB record page.

法規制情報

TSCA Requirements · 1 件

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. (1,1'-Biphenyl)-4-ol is included on this list.

安全データ

wgk
2
tsca
TSCA listed
rtecs
DV5850000
ridadr
UN3077
毒性
LD50 ipr-mus: 150 mg/kg NTIS** AD691-490
hs_code
29071900
risk_code
36/37/38-51/53-38
化審法
(4)-19
hazard_code
Xi,N
safety_code
26-36/37-61-36
hazard_class
9
packing_group
III
Hazard Classifications
Aquatic Chronic 2Skin Irrit. 2Skin Sens. 1B
ストレージクラス
13 - Non Combustible Solids
有毒物質データの
92-69-3(Hazardous Substances Data)

Derivatives: bitertanol; phenolic resins, oil-soluble, non oil-reactive; phenolic resins, oil-soluble, oil-reactive

4-Hydroxybiphenyl is an intermediate for the production of varnish resins and nonionogenic emulsifiers which are used in the plant protection, polyurethane, and dyeing sectors.

U.S. Production2023: 75,000 - <500,000 lb
Industry UsesOther
Methods of Manufacturing · 5 件

FROM REACTION OF CHLOROBENZENE & CAUSTIC SODA SOLN @ ELEVATED TEMP & PRESSURE.

Biphenyl (sulphonation/alkali fusion; coproduced with o-phenylphenol)

Chlorobenzene (arylation/base-catalysed hydrolysis; coproduced with o-phenylphenol)

The alkaline fusion of arenesulfonic acid salts to yield phenols is used for the commercial manufacture of a variety of phenolic compounds including...4-hydroxybiphenyl...

4-Hydroxybiphenyl is formed alongside 2-hydroxybiphenyl as a byproduct in the alkaline pressure hydrolysis of chlorobenzene to phenol in 5-6% yield. The mixture consists of 2/3 ortho and 1/3 para isomer which can be separated by fractional distillation. 4-Hydroxybiphenyl can also be produced by sulfonation of biphenyl and alkaline fusion of the para-biphenylsulfonic acid.

General Manufacturing Information · 2 件

Transportation Equipment Manufacturing

[1,1'-Biphenyl]-4-ol: ACTIVE

応用分野 · 3 件

用途有機合成原料。

使用Fluorescence and phosphorescence quantum yields and fluorescence and phosphorescence lifetimes were obtained for 4-phenylphenol adsorbed on filter paper with either NaCl, NaBr, or NaI at 296 and 93 K. The solid-surface fluorescence and phosphorescence quantum yield values and phosphorescence lifetime values were obtained for p-aminobenzoic acid (PABA) and 4-phenylphenol adsorbed on α-cyclodextrin/NaCl mixtures. 4-Phenylphenol is used as an antioxidant and is a potential EDC.

一般的な説明4-Phenylphenol undergoes enzymatic polymerization and polymer developed is characterized by matrix-assisted laser desorption ionization time-of-flight mass spectrometry. It is the intermediate in manufacture of 4-alkyl substituted phenol-formaldehyde resins.

調製方法 · 2 件

製造方法4-phenylphenol synthesis: Add to a 50 ml round-bottom flask, in this order, 122 mg of phenylboronic acid, 414 mg of potassium carbonate, 220 mg of 4-iodophenol, and 10 ml of deionized water. Weigh in a suitably sized container 3 mg Pd on C 10%, add 1 ml of deionized water, and stir gently by hand to form a slurry that is then transferred to the reaction flask. Couple the flask to a water-jacketed condenser, and reflux the mixture on a hot plate with a magnetic stirrer vigorously for 30 min (until a precipitate appears). After this time, switch off the plate and allow to cool to r.t. Add HCl 2 M to an acidic pH (check with indicator paper). Separate the resulting solid, still containing the catalyst, by filtering with a Hirsch funnel. Wash the solid with 10 ml of water. Then, in a Hirsch funnel, add 10 ml of MeOH, and collect the filtrate in a clean container. Add to the resulting MeOH solution 10 ml of deionized water to obtain the precipitate of the product. Purify by recrystallization, heating in a water bath container with the precipitate and the MeOH/H2O mixture. If necessary, add 1 to 2 ml more of hot MeOH, to finish dissolving the solid. Filter under vacuum with a Hirsch funnel, air dry the solid (can recover the next day). Weigh and calculate the yield.

純化方法Crystallise the phenol from aqueous EtOH, *C6H6, and dry it in a vacuum over CaCl2 [Buchanan et al. J Am Chem Soc 108 7703 1986]. [Beilstein 6 IV 4600.]

上流・下流製品情報

上流原料

2-フェニルフェノールビフェニルトリクロロエチレン三酸化硫黄Mixed phenyl phenol2-フェニルフェノールナトリウム四水和物4-イソプロピルビフェニル4,4'-ビフェノール2-ヒドロキシ-3-ニトロビフェニル

下流製品

2-フェニルフェノールビフェナゼト4-ヒドロキシ-3,5-ジニトロビフェニル2-ニトロ-4-フェニルフェノール3-アミノ-4-メトキシビフェニル3-ブロモビフェニル-4-オール3-[[4-[2-(ソジオスルホオキシ)エトキシ]フェニル]アゾ][1,1'-ビフェニル]-4-オール

補足説明

定義ChEBI: 4-Phenylphenol is a member of the class of hydroxybiphenyls that is biphenyl carrying a hydroxy group at position 4.