4-氟-4'-羟基联苯 | 324-94-7

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟苯酚系列
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氟-4'-羟基联苯
• 中文别名: 4-氟-4’-羟基二苯；4-(4-氟苯基)苯酚；4'-氟联苯-1-醇；4-氟-4"-羟基联苯
• 英文名称: 4'-fluoro-biphenyl-4-ol
• 英文别名: 4'-fluoro-4-hydroxybiphenyl；4'-fluoro-[1,1'-biphenyl]-4-ol；4-hydroxy-4'-fluorobiphenyl；4-(4-fluorophenyl)phenol；4-(4-Fluor-phenyl)-phenol；4-(p-Fluorphenyl)-phenol；4-Fluoro-4'-hydroxybiphenyl
• CAS: 324-94-7
• 化学式: C₁₂H₉FO
• 分子量: 188.201
• InChiKey: QSJNKJGPJVOGPK-UHFFFAOYSA-N

物化性质

• 熔点：
  152°C
• 沸点：
  303.7±17.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 海关编码：
  2907199090
• 安全说明：
  S22,S26,S36/37/39,S45
• 危险类别码：
  R20/21/22,R37/38,R41,R48
• 危险品运输编号：
  UN 1090 3/PG 2
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H315,H319
• 储存条件：
  室温

SDS

4-Fluoro-4'-hydroxybiphenyl
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 4-Fluoro-4'-hydroxybiphenyl

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 4-Fluoro-4'-hydroxybiphenyl
Percent: >98.0%(GC)
CAS Number: 324-94-7
Synonyms: 4'-Fluorobiphenyl-1-ol , 4-(4-Fluorophenyl)phenol
C12H9FO
Chemical Formula:

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
4-Fluoro-4'-hydroxybiphenyl

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Section 4. FIRST AID MEASURES
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Crystal- Powder
Form:
Colour: White - Very pale yellow
No data available
Odour:
4-Fluoro-4'-hydroxybiphenyl

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
pH: No data available
Melting point/freezing point:172°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents]
Soluble: Methanol

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Hydrogen fluoride
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed
4-Fluoro-4'-hydroxybiphenyl

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

环氧树脂由于具备较高的机械强度、良好的粘接性和加工性能等优点，广泛应用于涂覆材料、模塑料及胶黏剂等领域。然而，其低断裂延伸率和较大的脆性促使研究人员对其进行了广泛的化学或物理改性研究。

4-氟-4'-羟基联苯可以作为原料之一，与1,4-丁二醇、1,6-己二醇、甲苯二异氰酸酯（TDI）、二甲胺及环氧氯丙烷共同合成一种联苯型液晶环氧化合物（LCE）。

制备过程中，在带有搅拌器、温度计和100 mL滴液漏斗的500 mL三颈瓶中，依次加入0.045 mol TMBP（10 g）、0.32 mol 吡啶（8 mL）及100 mL丙酮。将0.1 mol ABC（18 g）溶解在30 mL丙酮中，并通过滴液漏斗缓慢滴加至三颈瓶内。反应在冰水浴中进行约1小时，直至ABC丙酮溶液完全滴加完毕，然后继续在室温下反应8小时。

反应后，向混合物中加入过量的冰水以形成大量沉淀。过滤得到固体，并用氯仿/水（体积比1:1）溶剂洗涤并重结晶。最后，在真空烘箱中干燥后获得黄色粉末状产物。通过FT-IR和NMR光谱对该化合物进行结构表征，确认其为BABTMBP（P1）。

反应信息

• 作为反应物：
  描述：

  4-氟-4'-羟基联苯 在 potassium tert-butylate 、 苯肼 、 N,N'-二甲基乙二胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 对羟基联苯
  参考文献：
  名称：

  光诱导、苯肼促进的芳基氟化物、氯化物、溴化物和碘化物的无过渡金属脱卤

  摘要：

  在这项研究中，我们提出了一种直接且高效的芳基卤化物光触发氢化方法，无需过渡金属催化剂。通过光、PhNHNH2 和碱的协同利用，我们成功地引发了所需的自由基介导的氢化过程。值得注意的是，利用温和的反应条件，多种芳基卤化物，包括氟化物、氯化物、溴化物和碘化物，可以选择性地转化为其相应的（杂）芳烃对应物，且产率极高。此外，该方法表现出与不同官能团和杂环化合物的显着相容性，突出了其多功能性和在各种化学转化中使用的潜力。

  DOI：

  10.3390/molecules28196915
• 作为产物：
  描述：

  4-(叔丁基二甲基硅氧基)苯基硼酸 在 四(三苯基膦)钯 四丁基氟化铵 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 2.08h， 生成 4-氟-4'-羟基联苯
  参考文献：
  名称：

  Discovery of Potent Nonpeptide Inhibitors of Stromelysin Using SAR by NMR

  摘要：

  With the use of an NMR-based method, potent (IC50 < 25 nM) nonpeptide inhibitors of the matrix metalloproteinase stromelysin (MMP-3) were discovered. The method, called SAR by NMR (for structure-activity relationships by nuclear magnetic resonance), involves the identification, optimization, and linking of compounds that bind to proximal sites on a protein. Using this technique, two ligands that bind weakly to stromelysin (acetohydroxamic acid, K-D = 17 mM; 3-(cyanomethyl)-4'-hydroxybiphenyl, K-D = 0.02 mM) were identified. On the basis of NMR-derived structural information, the two fragments were connected to produce a 15 nM inhibitor of this enzyme. This compound was rapidly discovered (less than 6 months) and required only a minimal amount of chemical synthesis. These studies indicate that the SAR by NMR method can be effectively applied to enzymes to yield potent lead inhibitors-an important part of the drug discovery process.

  DOI：

  10.1021/ja9702778

文献信息

• Cross-coupling reactions with boronic acids in water catalysed by oxime-derived palladacycles
  作者：Luis Botella、Carmen Nájera

  DOI：10.1016/s0022-328x(02)01727-8

  日期：2002.12

  Palladacycles derived from phenone-oximes 1 are efficient precatalysts for the Suzuki–Miyaura coupling of arylboronic acids with aromatic and heteroaromatic bromides and chlorides under water reflux under aerobic conditions. Alternatively, the coupling can also be carried out at room temperature in methanol–water. Aryl bromides gave biaryls with TON up to 105 and TOF up to 7×104 h−1. Activated and

  衍生自苯酮肟1的Palladacycles是有氧条件下在水回流下芳烃硼酸与芳族和杂芳族溴化物和氯化物的Suzuki-Miyaura偶联的有效预催化剂。或者，也可以在室温下在甲醇-水中进行偶联。芳基溴化物使联芳基的TON高达10 5，TOF高达7×10 4 h -1。活化和失活的芳基氯化物需要存在TBAB才能偶联，表现出稍低的效率（TON高达9000，TOF高达3850 h -1）。C（sp 2）C（sp 3）也可以通过三甲基环硼氧烷和丁基硼酸与芳族溴化物和氯化物在水回流下以及苄基和烯丙基氯化物或乙酸酯与芳基硼酸在丙酮-水中在室温下的交叉偶联反应形成。
• Reverse hydroxamate inhibitors of matrix metalloproteinases
  申请人：Abbott Laboratories

  公开号：US06294573B1

  公开（公告）日：2001-09-25

  Compounds having the formula are matrix metalloproteinase inhibitors. Also disclosed are matrix metalloproteinase-inhibiting compositions and methods of inhibiting matrix metalloproteinase in a mammal.

  具有以下化学式的化合物是基质金属蛋白酶抑制剂。还公开了抑制基质金属蛋白酶的组合物和方法，用于在哺乳动物中抑制基质金属蛋白酶。
• Bis(imino)pyridine palladium(II) complexes as efficient catalysts for the Suzuki–Miyaura reaction in water
  作者：Ping Liu、Mei Yan、Ren He

  DOI：10.1002/aoc.1591

  日期：——

  Bis(imino)pyridine palladium(II) complexes 3 and 4 of type [PdCl(L)PF6] are found to be efficient catalysts for Suzuki–Miyaura reactions of aryl halides and arylboronic acids. The reactions proceed smoothly to generate the corresponding biaryl compounds in moderate to excellent yields. The synthesis of various fluorinated biphenyl derivatives was successfully achieved by the complex 4 catalyzed the Suzuki–Miyaura

  发现[PdCl（L）PF 6 ]型双（亚氨基）吡啶钯（II）配合物3和4是芳基卤化物和芳基硼​​酸的Suzuki-Miyaura反应的有效催化剂。反应平稳进行，以中等至优异的产率产生相应的联芳基化合物。在带有长烷基链的表面活性剂的存在下，通过配合物4催化Suzuki-Miyaura反应成功地完成了各种氟化联苯衍生物的合成。版权所有©2009 John Wiley＆Sons，Ltd.
• PEG Click-Triazole Palladacycle: An Efficient Precatalyst for Palladium-Catalyzed Suzuki-Miyaura and Copper-free Sonogashira Reactions in Neat Water
  作者：Guofu Zhang、Wei Zhang、Yuxin Luan、Xingwang Han、Chengrong Ding

  DOI：10.1002/cjoc.201500167

  日期：2015.7

  A novel water‐soluble, phosphine‐free PEG "click" triazole palladacycle has been successfully synthesized. As a precatalyst, the palladacycle exhibited superior catalytic activity towards Suzuki‐Miyaura and copper‐free Sonogashira cross‐coupling in neat water with the turnover numbers (TONs) of up to 9.8×105. In addition, the catalyst could be reused at least 3 times without significant loss of reactivity

  已经成功合成了一种新型的水溶性，无膦的PEG“点击”三唑palladacycle。palladacycle作为前催化剂在纯净水中对铃木宫浦和无铜Sonogashira交叉偶联表现出优异的催化活性，周转数（TONs）高达9.8×10 5。此外，该催化剂可以重复使用至少3次，而不会显着降低反应性。
• A convenient chemical-microbial method for developing fluorinated pharmaceuticals
  作者：Tara V. Bright、Fay Dalton、Victoria L. Elder、Cormac D. Murphy、Neil K. O'Connor、Graham Sandford

  DOI：10.1039/c2ob27140k

  日期：——

  A significant proportion of pharmaceuticals are fluorinated and selecting the site of fluorine incorporation can be an important beneficial part a drug development process. Here we describe initial experiments aimed at the development of a general method of selecting optimum sites on pro-drug molecules for fluorination, so that metabolic stability may be improved. Several model biphenyl derivatives were transformed by the fungus Cunninghamella elegans and the bacterium Streptomyces griseus, both of which contain cytochromes P450 that mimic oxidation processes in vivo, so that the site of oxidation could be determined. Subsequently, fluorinated biphenyl derivatives were synthesised using appropriate Suzuki–Miyaura coupling reactions, positioning the fluorine atom at the pre-determined site of microbial oxidation; the fluorinated biphenyl derivatives were incubated with the microorganisms and the degree of oxidation assessed. Biphenyl-4-carboxylic acid was transformed completely to 4′-hydroxybiphenyl-4-carboxylic acid by C. elegans but, in contrast, the 4′-fluoro-analogue remained untransformed exemplifying the microbial oxidation – chemical fluorination concept. 2′-Fluoro- and 3′-fluoro-biphenyl-4-carboxylic acid were also transformed, but more slowly than the non-fluorinated biphenyl carboxylic acid derivative. Thus, it is possible to design compounds in an iterative fashion with a longer metabolic half-life by identifying the sites that are most easily oxidised by in vitro methods and subsequent fluorination without recourse to extensive animal studies.

  大部分药物含有氟元素，在药物开发过程中，选择氟元素的加入位置可能是一个有益的环节。在这里，我们描述了初始实验，旨在开发一种通用方法，选择前药分子上最佳的氟化位置，以提高代谢稳定性。通过含有细胞色素P450的真菌和细菌分别对几种联苯衍生物进行转化，这些细胞色素P450模拟了体内的氧化过程，从而确定了氧化位置。随后，利用适当的铃木-宫浦偶联反应合成了氟化联苯衍生物，将氟原子置于预定微生物氧化的位置；这些氟化联苯衍生物与微生物共培养，并评估了氧化程度。结果显示，联苯-4-羧酸被Cunninghamella elegans完全转化为4′-羟基联苯-4-羧酸，但4′-氟代衍生物保持不变，证明了微生物氧化-化学氟化的概念。2′-氟代和3′-氟代联苯-4-羧酸也能被转化，但速度比未氟化的联苯羧酸衍生物慢。因此，可以通过体外方法确定最容易氧化的位置，然后进行氟化，迭代设计代谢半衰期更长的化合物，无需依赖大量的动物研究。

表征谱图