4-甲氧基萘-1-硼酸 | 219834-95-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4-甲氧基萘-1-硼酸
• 中文别名: (4-甲氧基-1-萘基)硼酸
• 英文名称: (4-methoxynaphthalen-1-yl)boronic acid
• 英文别名: 4-methoxy-1-naphthaleneboronic acid；4-methoxy-1-naphthylboronic acid
• CAS: 219834-95-4
• 化学式: C₁₁H₁₁BO₃
• 分子量: 202.018
• InChiKey: UNEURVGVRYJOMG-UHFFFAOYSA-N

物化性质

• 熔点：
  195 °C
• 沸点：
  413.8±47.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2931900090
• 危险标志：
  GHS05
• 危险性描述：
  H318
• 危险性防范说明：
  P280,P305 + P351 + P338

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Methoxynaphthalen-1-ylboronic acid
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: 4-Methoxynaphthalen-1-ylboronic acid
CAS number: 219834-95-4

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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, under −20◦C.
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: C11H11BO3
Molecular weight: 202.0

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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：

  4-甲氧基萘-1-硼酸 在 四(三苯基膦)钯 、 C₃₃H₃₁O₂Rh 、 copper diacetate 、 sodium carbonate 、 silver carbonate 、 过氧化苯甲酰 作用下， 以 甲醇 、 乙二醇二甲醚 、 水 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  铑催化联芳基化合物与烯烃的不对称脱氢缩合氢键的轴向手性

  摘要：

  通过直接的CH键官能化反应实现了轴向手性联芳基的对映选择性结构。使用手性[Cp * Rh III ]催化剂，通过联芳基化合物的直接CH键烯化反应合成了新型的轴向手性联芳基，具有良好的收率和对映选择性。发现获得的轴向手性联芳基是铑催化的不对称共轭物加成的合适配体。

  DOI：

  10.1002/anie.201408805
• 作为产物：
  描述：

  1-甲氧基萘 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 26.0h， 生成 4-甲氧基萘-1-硼酸
  参考文献：
  名称：

  Material for organic electroluminescence device and organic electroluminescence device using the same

  摘要：

  本发明揭示了一种有机材料，其由以下公式（A）表示，采用该材料作为发光层的发光主体或掺杂剂的有机EL器件，可以显示出良好的性能。其中A代表具有两到三个环的取代或未取代的融合环烃基元，m代表0到10的整数，G、Rs和R1到R3的定义与本发明中描述的相同。

  公开号：

  US09537103B1

文献信息

• Pd-catalyzed asymmetric Suzuki–Miyaura coupling reactions for the synthesis of chiral biaryl compounds with a large steric substituent at the 2-position
  作者：Yongsu Li、Bendu Pan、Xuefeng He、Wang Xia、Yaqi Zhang、Hao Liang、Chitreddy V Subba Reddy、Rihui Cao、Liqin Qiu

  DOI：10.3762/bjoc.16.85

  日期：——

  Pd-catalyzed asymmetric Suzuki–Miyaura couplings of 3-methyl-2-bromophenylamides, 3-methyl-2-bromo-1-nitrobenzene and 1-naphthaleneboronic acids have been successfully developed and the corresponding axially chiral biaryl compounds were obtained in very high yields (up to 99%) with good enantioselectivities (up to 88% ee) under mild conditions. The chiral-bridged biphenyl monophosphine ligands developed

  已成功开发了Pd催化的3-甲基-2-溴苯基酰胺，3-甲基-2-溴-1-硝基苯和1-萘硼酸的不对称Suzuki-Miyaura偶联，并以很高的收率获得了相应的轴向手性联芳基化合物（最高99％），在温和条件下具有良好的对映选择性（最高88％ee）。由我们小组开发的手性桥联联苯基单膦配体在反应性和对映选择性控制方面均显示出优于萘基对应MOP的优势。溴苯底物的π共轭邻位取代基的较大位阻以及羰基与钯之间的Pd··O相互作用似乎对实现高对映选择性至关重要。
• Electrochemical Synthesis of Biaryls via Oxidative Intramolecular Coupling of Tetra(hetero)arylborates
  作者：Arif Music、Andreas N. Baumann、Philipp Spieß、Allan Plantefol、Thomas C. Jagau、Dorian Didier

  DOI：10.1021/jacs.9b12300

  日期：2020.3.4

  scope, scalability and robustness of this unconventional catalyst-free transformation, leading to functional-ized biaryls and ultimately furnishing drug-like small molecules as well as late stage derivatization of natural compounds. In addition, the observed selectivity of the oxidative coupling reaction is related to the electronic structure of the TABs through quantum-chemical calculations and experimental

  我们在此报告了由三氟芳基硼酸钾的配体交换反应制备的不对称四（杂）芳基硼酸盐（TAB）的氧化电偶联促进的多功能、无过渡金属和无添加剂的（杂）芳基-芳基偶联反应。该方法利用电化学氧化的能力，补充了现有的有机硼工具箱。我们展示了这种非常规无催化剂转化的广泛范围、可扩展性和稳健性，导致功能化联芳并最终提供类药物小分子以及天然化合物的后期衍生化。此外，通过量子化学计算和实验研究，观察到的氧化偶联反应的选择性与 TAB 的电子结构有关。
• [EN] CARBOXAMIDE OR SULFONAMIDE SUBSTITUTED THIAZOLES AND RELATED DERIVATIVES AS MODULATORS FOR THE ORPHAN NUCLEAR RECEPTOR ROR[GAMMA]<br/>[FR] THIAZOLES SUBSTITUÉS PAR CARBOXAMIDE OU SULFONAMIDE ET DÉRIVÉS APPARENTÉS EN TANT QUE MODULATEURS DU RÉCEPTEUR NUCLÉAIRE ORPHELIN ROR[GAMMA]
  申请人：PHENEX PHARMACEUTICALS AG

  公开号：WO2013178362A1

  公开（公告）日：2013-12-05

  The invention provides modulators for the orphan nuclear receptor RORy and methods for treating RORy mediated diseases by administering these novel RORy modulators to a human or a mammal in need thereof. Specifically, the present invention provides carboxamide or sulfonamide containing cyclic compounds of Formula (1), (1'), (100), (100'), (200) and (200') and the enantiomers, diastereomers, tautomers, /V-oxides, solvates and pharmaceutically acceptable salts thereof.

  这项发明提供了用于孤儿核受体RORγ的调节剂，以及通过向需要的人类或哺乳动物投与这些新型RORγ调节剂来治疗RORγ介导的疾病的方法。具体而言，本发明提供了含有环状化合物的羧酰胺或磺酰胺的化合物的公式（1）、（1'）、（100）、（100'）、（200）和（200'）及其对映体、二对映体、互变异构体、/V-氧化物、溶剂合物和药用可接受盐。
• Efficient Chiral Monophosphorus Ligands for Asymmetric Suzuki–Miyaura Coupling Reactions
  作者：Wenjun Tang、Nitinchandra D. Patel、Guangqing Xu、Xiaobing Xu、Jolaine Savoie、Shengli Ma、Ming-Hong Hao、Santosh Keshipeddy、Andrew G. Capacci、Xudong Wei、Yongda Zhang、Joe J. Gao、Wenjie Li、Sonia Rodriguez、Bruce Z. Lu、Nathan K. Yee、Chris H. Senanayake

  DOI：10.1021/ol300659d

  日期：2012.5.4

  A series of novel P-chiral monophosphorus ligands exhibit efficiency in asymmetric Suzuki–Miyaura coupling reactions, enabling the construction of an array of chiral biaryl products in high yields and excellent enantioselectivities (up to 96% ee) under mild conditions. The carbonyl-benzooxazolidinone moiety in these chiral biaryl products allows facile derivatization for further synthetic applications

  一系列新颖的P-手性单磷配体在不对称Suzuki-Miyaura偶联反应中表现出效率，使得在温和条件下能够以高收率和出色的对映选择性（高达96％ee）构建一系列手性联芳基产品。这些手性联芳基产物中的羰基-苯并恶唑烷酮部分允许容易地衍生化，以用于进一步的合成应用。一项计算研究表明，两个偶联伙伴之间的π-π相互作用可以增强偶联反应的对映选择性。
• 一种小分子有机电致发光材料及其应用
  申请人：中节能万润股份有限公司

  公开号：CN105669527A

  公开（公告）日：2016-06-15

  本发明涉及一种小分子有机电致发光材料及其应用，该类材料具有符合式(Ⅰ)所示的分子结构，该类材料具有良好的薄膜稳定性、合适的分子能级，可以作为有机电致发光器件的功能层，应用在有机电致发光领域中。