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Biphenyl-4-ol
[1,1'-Biphenyl]-4-ol · BIPHENYL-4-OL · P-PHENYLPHENOL · P-HYDROXYBIPHENYL · 4-HYDROXYBIPHENYL · 4-pp · 4-HYDROXYDIPHENYL · (1,1’-Biphenyl)-4-ol
Identifikatoren & physikalische Daten
| CAS No. | 1322-20-9 |
|---|---|
| Summenformel | C12H10O |
| Durchschnittliche Molmasse | 170,21 g/mol |
| Monoisotopische Masse | 170,07316494 g/mol |
| SMILES | Oc1ccc(-c2ccccc2)cc1 |
| InChIKey | YXVFYQXJAXKLAK-UHFFFAOYSA-N |
| PubChem CID | 7103 |
| ChEMBL | CHEMBL73380 |
| ChEBI | CHEBI:34422 |
| EC No. | 202-179-2 |
| DTXSID | DTXSID7021152 |
| Lokaler Name | Biphenyl-4-ol |
Chemische & physikalische Eigenschaften
| XLogP | 3,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 20,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 141 |
| Stoffklassen | Other Classes -> Other Aromatic Compounds |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP (Verteilungskoeffizient) | Log Kow = 3.203.33 |
| Dichte | 1.27 kg/l @ 25 °C1.27 @25 °C1.0149 (rough estimate) |
| Color/Form | NEARLY WHITE CRYSTALSNEEDLES OR PLATES FROM DILUTE ALCOHOLWhite flakes |
| Löslichkeit | SLIGHTLY SOL IN PETROLEUM ETHERVERY SOL IN ALCOHOL, ETHER, CHLOROFORM & PYRIMIDINESOL IN ALCOHOL, ALSO IN ALKALIES & MOST ORGANIC SOLVENTSINSOLUBLE IN WATERSoluble in oxygenated solvents.Water solubility = 56.2 mg/lmethanol: soluble50mg/mL, clear, colorless0.7 g/L (20 ºC) |
| Flammpunkt | 165.5 °C330 °F |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Siedepunkt | 305-308 °C321 °C (lit.) |
| Schmelzpunkt | 164-165 °C164-166 °C (lit.) |
| Dampfdruck | 0.0000188 [mmHg]0Pa at 25℃ |
| Food Contact Substances | FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR |
| Brechungsindex | 1.6188 (estimate) |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Aggregatzustand | Flakes |
| pKa (Säurekonstante) | 9.55(at 25℃) |
| Farbe | White to slightly yellow |
| pH | 7 (0.7g/l, H2O, 20℃) |
| Merck | 14,7305 |
| BRN | 1907452 |
| Henry-Konstante | 1.6×10-1 mol/(m3Pa) at 25℃, Mackay et al. (2006) |
| Stabilität | Stable. Incompatible with strong oxidizing agents, strong bases, halogens. Combustible. |
| 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 (Verteilungskoeffizient) | 3.6 at 25℃ |
| CAS Datenbank | 92-69-3(CAS DataBase Reference) |
| NIST chemische Informationen | p-Hydroxybiphenyl(92-69-3) |
| EPA chemische Informationen | 4-Phenylphenol (92-69-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (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. |
|---|---|
| Regulatorische Informationen | 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 |
| Gefahrenübersicht | A tumorigenIntraperitoneal LD50 (mouse) = 150 mg/kg[RTECS] Emergency treatment: see Biphenyl. [HSDB] An irritant[MSDSonline] See Biphenyl. |
| TSCA-Anforderungen | 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 Categories | Skin Irrit. 2 (98.4%) |
| Entsorgungsverfahren | 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) | 0.49 [mg/m3]5.4 [mg/m3]32 [mg/m3] |
| Umweltverhalten | 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 sludgeover 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 sludgeover 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). |
| Unerwünschte Wirkungen | Neurotoxin - Other CNS neurotoxin |
| Effluent Concentrations | 4-Hydroxybiphenyl was measured in a standard reference diesel particulate sample (NBS 1650) at unreported concentrations(1). |
| Soil Adsorption/Mobility | 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 Sources | 4-Hydroxybiphenyl is formed as a reaction product from the photolysis of 4-chlorobiphenol in water(1). |
| Human Toxicity Excerpts | MODERATELY TOXIC BY INGESTION. |
| Artificial Pollution Sources | 4-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 | 4-Hydroxybiphenyl at 30 mg/L was inoculated with activated sludgeover 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 Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Environmental Bioconcentration | 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 | 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 | 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. |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN3077 |
| Zollcode | 29071900 |
| RTECS-Nr. | DV5850000 |
| R-Sätze (R) | 36/37/38-51/53-38 |
| Toxizität | LD50 ipr-mus: 150 mg/kg NTIS** AD691-490 |
| Gefahrensymbole | Xi,N |
| Sicherheitshinweise (S) | 26-36/37-61-36 |
| Gefahrenklasse | 9Aquatic Chronic 2Skin Irrit. 2Skin Sens. 1B |
| Verpackungsgruppe | III |
| Lagerklasse | 13 - Non Combustible Solids |
| Gefahrstoffdaten | 92-69-3(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
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.
Herstellung & Synthese
synthetische
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.