기본 정보
- 표준 SMILES
Oc1ccc(-c2ccccc2)cc1- InChIKey
YXVFYQXJAXKLAK-UHFFFAOYSA-N- 분자식
- C12H10O
- 평균 분자량
- 170.21 g/mol
- 단동위원소 질량
- 170.07316494
개요
Biphenyl-4-ol is a member of the class of hydroxybiphenyls that is biphenyl carrying a hydroxy group at position 4.
이름 및 식별자
- 우선 이름
- 4-Hydroxybiphenyl
- IUPAC
- 4-phenylphenol
- 현지명
- p-페닐페놀
- 영어명
- 4-Phenylphenol
- 분자식
- C12H10O
- 분자량
- 170.21
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- 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
물성
구조 계산 물성
- XLogP
- 3.2
- 극성 표면적
- 20.2 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 1
- 회전 가능 결합 수
- 1
- 무거운 원자 수
- 13
- 형식 전하
- 0
- 복잡도
- 141
실험 및 물리화학적 성질
LogP
Log Kow = 3.20
3.33
Density
1.27 kg/l @ 25 °C
1.27 @25 °C
Color/Form
NEARLY WHITE CRYSTALS
NEEDLES OR PLATES FROM DILUTE ALCOHOL
White flakes
Solubility
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
165.5 °C
330 °F
물리화학적 성질
- 녹는점
- 164 · 164-166 °C (lit.)
- 끓는 점
- 321 °C · 321 °C (lit.)
- 밀도
- 1.0149 · 1.0149 (rough estimate)
- 증기압
- 0 Pa · 0Pa at 25℃
- 굴절률
- 1.6188 · 1.6188 (estimate)
- 인화점
- 330 °F · 330 °F
- 저장 조건
- Sealed in dry,Room Temperature
- 용해도
- 50 mg/mL, · 메탄올: 용해성50mg/mL, 투명, 무색
- 물리적 상태
- 플레이크
- 산도 계수 (pKa)
- 9.55 · 9.55(at 25℃)
- 색상
- 흰색에서 약간 노란색
- 수소이온지수(pH)
- 7 · 7 (0.7g/l, H2O, 20℃)
- 수용성
- 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)
- 안정성
- 안정적인. 강산화제, 강염기, 할로겐과 호환되지 않습니다. 타기 쉬운.
- 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℃
- NIST
- p-Hydroxybiphenyl(92-69-3)
- EPA
- 4 · 4-Phenylphenol (92-69-3)
화학적 성질
light tan solid (odour threshold detection limit 0.7 ppm)
안전 및 규제
GHS 분류
GHS Classification
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.
유해성 정보
Regulatory Information
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
TSCA Requirements
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.
안전 및 보호
Disposal Methods
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]
독성 정보
Environmental Fate
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).
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).
Environmental Biodegradation
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).
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.
규제 정보
TSCA Requirements
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.
안전 데이터
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- DV5850000
- ridadr
- UN3077
- 독성
- LD50 ipr-mus: 150 mg/kg NTIS** AD691-490
- HS 번호
- 29071900
- risk_code
- 36/37/38-51/53-38
- hazard_code
- Xi,N
- safety_code
- 26-36/37-61-36
- 포장분류
- III
- 위험 등급
- 9
- 기존화학 물질
- KE-02871
- Hazard Classifications
- Aquatic Chronic 2Skin Irrit. 2Skin Sens. 1B
- 스토리지 클래스
- 13 - Non Combustible Solids
- 유해 물질 데이터
- 92-69-3(Hazardous Substances Data)
화학 및 산업
약리 정보
Mechanism of Action
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
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.
용도 및 제조
Uses
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
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.
Methods of Manufacturing
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
Transportation Equipment Manufacturing
[1,1'-Biphenyl]-4-ol: ACTIVE
응용 분야
용도Fluorescence 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.
일반 설명4-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.
제조 방법
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.
상·하류 제품 정보
상류 원료
하류 제품
공급사50 곳
추가 설명
정의ChEBI: 4-Phenylphenol is a member of the class of hydroxybiphenyls that is biphenyl carrying a hydroxy group at position 4.
관련 반응
연결된 노트
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