3-hydroxy-4-methoxybiphenyl | 37055-80-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-hydroxy-4-methoxybiphenyl
• 英文别名: 2-methoxy-5-phenylphenol
• CAS: 37055-80-4
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: HKJUJKFXUPMEKB-UHFFFAOYSA-N

物化性质

• 熔点：
  108.6 °C(Solv: methanol (67-56-1))
• 沸点：
  357.4±35.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2909500000

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Methoxy-5-phenylphenol
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Methoxy-5-phenylphenol
CAS number: 37055-80-4

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C13H12O2
Molecular weight: 200.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-hydroxy-4-methoxybiphenyl 在 氢氧化钾 、 sodium azide 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 2-(2-叠氮乙氧基)-1-甲氧基-4-苯基苯
  参考文献：
  名称：

  WB4101-Related Compounds:  New, Subtype-Selective α₁-Adrenoreceptor Antagonists (or Inverse Agonists?)

  摘要：

  Our previous structure-affinity relationship study had considered the enantiomers of the naphthodioxane, tetrahydronaphthodioxane, and 2-methoxy-1-naphthoxy analogues ( compounds 1, 3, and 2, respectively) of 2-(2,6-dimethoxyphenoxyethylaminomethyl)-1,4-benzodioxane, the well-known alpha(1)-adrenoceptor (alpha(1)-AR) antagonist WB4101, showing that such modifications significantly modulate the affinity and selectivity profile for alpha(1)-AR subtypes and 5-HT1A receptor. Here, we extend investigations to antagonist activity enclosing new enantiomeric pairs, namely those of the methoxytetrahydronaphthoxy and methoxybiphenyloxy WB4101 analogues (4 and 5-7, respectively) and of a double- modified WB4101 derivative ( 8) resulting from hybridization between 2 and 3. We found that (S)-2 is a very potent (pA(2) 10.68) and moderately selective alpha(1D)-AR antagonist and the hybrid (S)-8 is a potent (pA(2) 7.98) and highly selective alpha(1A)-AR antagonist. Both of these compounds and (S)-WB4101 seem to act as inverse agonists in a vascular model. The results, which generally validate the logic we followed in designing these eight compounds, are acceptably rationalized by comparative SAR analysis of binding and functional affinities.

  DOI：

  10.1021/jm060358r
• 作为产物：
  描述：

  2-(4-hydroxy-biphenyl-3-yloxy)-5-nitro-benzophenone 在 哌啶 作用下， 生成 3-hydroxy-4-methoxybiphenyl
  参考文献：
  名称：

  54.苯酚的邻羟基氧化。第二部分 邻苯二酚的衍生物

  摘要：

  DOI：

  10.1039/jr9530000265

文献信息

• Direct Hydroxylation and Amination of Arenes via Deprotonative Cupration
  作者：Noriyuki Tezuka、Kohei Shimojo、Keiichi Hirano、Shinsuke Komagawa、Kengo Yoshida、Chao Wang、Kazunori Miyamoto、Tatsuo Saito、Ryo Takita、Masanobu Uchiyama

  DOI：10.1021/jacs.6b03855

  日期：2016.7.27

  Deprotonative directed ortho cupration of aromatic/heteroaromatic C-H bond and subsequent oxidation with t-BuOOH furnished functionalized phenols in high yields with high regio- and chemoselectivity. DFT calculations revealed that this hydroxylation reaction proceeds via a copper (I → III → I) redox mechanism. Application of this reaction to aromatic C-H amination using BnONH2 efficiently afforded

  芳族/杂芳族 CH 键的去质子定向邻铜化和随后用 t-BuOOH 氧化以高产率和高区域选择性和化学选择性提供官能化酚。DFT 计算表明，这种羟基化反应是通过铜 (I → III → I) 氧化还原机制进行的。将该反应应用于使用 BnONH2 的芳族 CH 胺化有效地提供了相应的伯苯胺。这些反应显示出广泛的范围和良好的官能团兼容性。还展示了这些转化的催化版本。
• A New Entry to the Synthesis of 1,2-Benzenediol Congeners.
  作者：Yutaka OZAKI、Ikumi OSHIO、Yasue OHSUGA、Shouichi KABURAGI、Zhung-Zhu SUNG、Sang-Won KIM

  DOI：10.1248/cpb.39.1132

  日期：——

  1, 2-Benzenediols were synthesized via 1, 1-bis(ethylthio)-3-cyclohexen-2-one derivatives, which were prepared by condensation of 1, 1-bis(ethylthio)-2-propanone with Mannich bases. Regioselective preparation of their monoethers was also achieved.

  1, 2-苯二醇通过1, 1-双(乙硫基)-3-环己烯-2-酮衍生物合成，这些衍生物是通过1, 1-双(乙硫基)-2-丙酮与曼尼希碱的缩合反应制备的。同时，单醚的位选择性合成也得以实现。
• Tuning the Reactivity of Peroxo Anhydrides for Aromatic C–H Bond Oxidation
  作者：Afsaneh Pilevar、Abolfazl Hosseini、Marina Šekutor、Heike Hausmann、Jonathan Becker、Kevin Turke、Peter R. Schreiner

  DOI：10.1021/acs.joc.8b01392

  日期：2018.9.7

  demanding cyclic peroxide (spiro[bicyclo[2.2.1]heptane-2,4′-[1,2]dioxolane]-3′,5′-dione, P4) for the direct hydroxylation of aromatic substrates. The new peroxide benefits from high thermal stability and can be synthesized from readily available starting materials. The aromatic C–H oxidation using P4 exhibits generally good yields (up to 96%) and appreciable regioselectivities.

  从聚合物到药物，许多化学研究领域中的酚部分都是关键的结构基序。在此，我们报告了结构上苛刻的环状过氧化物（螺[双环[2.2.1]庚烷-2,4'-[1,2]二氧戊环] -3'，5'-二酮，P4）的设计和使用。芳族底物的直接羟基化。新的过氧化物具有高的热稳定性，可以由容易获得的起始原料合成。使用P4进行的芳族CH氧化通常显示出良好的产率（高达96％）和可观的区域选择性。
• Substitution of Hydroxybiaryls via Directed <i>o</i><i>rtho</i>-Lithiation of <i>N</i>-Silylated <i>O</i>-Aryl <i>N</i>-Isopropylcarbamates
  作者：Matthias Kauch、Victor Snieckus、Dieter Hoppe

  DOI：10.1021/jo0506938

  日期：2005.9.1

  Herein we report regioselective substitution reactions of a series of 2- and 3-hydroxybiaryls including BINOL via a new directed ortho-metalation procedure. O-Aryl N-isopropylcarbamates, conveniently prepared from phenols and isopropyl isocyanate, are temporarily and in situ N-protected by means of silyl triflates to form stable intermediates for low temperature lithiation reactions using butyllithium/TMEDA

  本文我们报告了一系列的2-和3- hydroxybiaryls包括通过新定向BINOL的区域选择性取代反应邻-metalation过程。方便地由苯酚和异氰酸异丙酯制备的O-芳基N-异丙基氨基甲酸酯通过使用丁基锂/ TMEDA在乙醚中的甲硅烷基三氟甲磺酸酯进行临时和原位N-保护，以形成用于低温锂化反应的稳定中间体。所得的芳基锂有效地被各种亲电试剂取代，从而以高收率提供官能化的联芳基。ñ-在水处理过程中已经发生了甲硅烷基化反应。氨基甲酸酯随后脱保护为相应的酚的过程迅速且以定量收率进行。产物中甚至敏感的取代基（例如，CO 2 Me，CHO，SiMe 3，I）也可以在温和的碱性条件下保存，这对于氨基甲酸酯的裂解已被确定。此外，还证明了邻位取代产物在常见的交叉偶联反应中进一步形成C-C键的应用。
• Synthesis of aryl-substituted 2-methoxyphenol derivatives from maltol-derived oxidopyrylium cycloadducts through an acid-mediated ring contraction cascade
  作者：Lauren P. Bejcek、Ryan P. Murelli

  DOI：10.1039/c9cc09213g

  日期：——

  Oxidopyrylium cycloadducts derived from maltol and aryl acetylenes undergo acid-mediated rearrangements to generate aryl-substituted 2-methoxyphenol (guaiacol) derivatives. Specifically, the cycloadducts react with boron trichloride to form 2-methoxy-5-arylphenol molecules, and with methane sulfonate to form 2-methoxy-4-aryl-6-methylphenol molecules.

  源自麦芽酚和芳基乙炔的氧化吡咯鎓环加合物经过酸介导的重排，生成芳基取代的 2-甲氧基苯酚（愈创木酚）衍生物。具体地，环加合物与三氯化硼反应形成2-甲氧基-5-芳基苯酚分子，并与甲磺酸酯反应形成2-甲氧基-4-芳基-6-甲基苯酚分子。