8-喹啉硼酸频哪醇酯 | 190788-62-6

• 物质功能分类: 化学试剂 - 有机试剂 - 磺酸/亚磺酸
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 8-喹啉硼酸频哪醇酯
• 中文别名: 喹啉-8-硼酸频哪醇酯
• 英文名称: 8-quinolineboronic acid pinacol ester
• 英文别名: 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline
• CAS: 190788-62-6
• 化学式: C₁₅H₁₈BNO₂
• 分子量: 255.124
• InChiKey: RNTGVJBKPQOGPS-UHFFFAOYSA-N

物化性质

• 沸点：
  386.5±15.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Quinoline-8-boronic acid, pinacol ester
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: Quinoline-8-boronic acid, pinacol ester
CAS number: 190788-62-6

---

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.

---

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.

---

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.

---

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, refrigerated.
Storage:

---

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.

---

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: C15H18BNO2
Molecular weight: 255.1

---

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

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

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

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  8-喹啉硼酸频哪醇酯 在 air 作用下， 以 乙腈 为溶剂， 生成 8,16-dihydroxy-8,16-epoxy[1,5,2,6]diazadiborocino[1,8,7-ij:5,4,3-i′j′]diquinoline
  参考文献：
  名称：

  Hydrolysis of 8-(pinacolboranyl)quinoline: where is the 8-quinolylboronic acid?

  摘要：

  合成了化合物8-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)-喹啉，并发现其在空气中迅速水解；然而，并未观察到预期产物（喹啉-8-基）硼酸。相反，根据水解条件，观察到（喹啉-8-基）三羟基硼酸酰离子或一种酸酐。两种产物在水化程度上相互关联，两种形式可以相互转化。两种水解产物的结构得到了表征。此外，商业样品“8-喹啉基硼酸”实际上被发现是酸酐。这些结果质疑了单体（喹啉-8-基）硼酸是否真的可以以中性路易斯碱无形式分离出来。

  DOI：

  10.1515/znb-2015-0031
• 作为产物：
  描述：

  苯基三氟甲烷磺酸酯 、 8-喹啉三氟甲烷磺酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 1,1'-双(二苯基膦)二茂铁 、 potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 39.0h， 以65%的产率得到8-喹啉硼酸频哪醇酯
  参考文献：
  名称：

  通过钯（0）催化四（烷氧基）二硼与芳基三氟甲磺酸酯的交叉偶联反应合成芳基硼酸酯

  摘要：

  （RO）2 BB（OR）2（RO =甲氧基和频哪醇）与芳基三氟甲磺酸酯的交叉偶联反应生成芳基硼酸酯，是在80°C的PdCl 2（dppf）（3 mol％）存在下进行的， dppf（3 mol％）和KOAc（3当量）的二恶烷溶液。该反应具有各种官能团，例如硝基，氰基，酯和羰基。

  DOI：

  10.1016/s0040-4039(97)00642-4

文献信息

• Remarkably Efficient Iridium Catalysts for Directed C(sp²)–H and C(sp³)–H Borylation of Diverse Classes of Substrates
  作者：Md Emdadul Hoque、Mirja Md Mahamudul Hassan、Buddhadeb Chattopadhyay

  DOI：10.1021/jacs.0c13415

  日期：2021.4.7

  aliphatic substrates for selective C(sp3)–H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C–H bonds. A number of late-stage C–H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)–H and C(sp3)–H borylations enabling the method more general

  在这里，我们描述了一类新的 C-H 硼化催化剂的发现及其在芳族、杂芳族和脂肪族系统的区域选择性 C-H 硼化中的应用。新催化剂具有 Ir-C(噻吩基) 或 Ir-C(呋喃基) 阴离子配体，而不是标准 C-H 硼化条件中使用的二胺型中性螯合配体。据报道，这些新发现的催化剂的使用对不同种类的芳烃底物显示出优异的反应性和邻位选择性，并具有高分离产率。此外，该催化剂被证明对大量脂肪族底物的选择性 C(sp 3)–H 键硼化。杂环分子利用 C-H 键固有的高反应性选择性地硼化。已经使用相同的催化剂描述了许多后期 C-H 功能化。此外，我们表明其中一种催化剂甚至可以在露天用于 C(sp 2 )-H 和 C(sp 3 )-H 硼酸化，从而使该方法更加通用。初步的机理研究表明，活性催化中间体是 Ir(bis)boryl 络合物，连接的配体作为双齿配体。总的来说，这项研究强调了新型 C-H 硼酸化催化剂的发现，这些催化剂应该在
• Spectroscopic Studies of the Chan–Lam Amination: A Mechanism-Inspired Solution to Boronic Ester Reactivity
  作者：Julien C. Vantourout、Haralampos N. Miras、Albert Isidro-Llobet、Stephen Sproules、Allan J. B. Watson

  DOI：10.1021/jacs.6b12800

  日期：2017.4.5

  of amine and organoboron reactivity issues, and the origin of competing oxidation/protodeboronation side reactions. Identification of key mechanistic events has allowed the development of a simple solution to these issues: manipulating Cu(I) → Cu(II) oxidation and exploiting three synergistic roles of boric acid has allowed the development of a general catalytic Chan-Lam amination, overcoming long-standing

  我们报告了对 Chan-Lam 胺化反应的调查。光谱学、计算模型和晶体学的结合已经确定了关键中间体的结构，并允许呈现完整的机制描述，包括非循环抑制过程、胺和有机硼反应性问题的来源，以及竞争氧化的起源/原脱硼副反应。关键机制事件的识别使得开发出解决这些问题的简单方法：操纵 Cu(I) → Cu(II) 氧化和利用硼酸的三种协同作用，开发了通用催化 Chan-Lam 胺化，克服了这种有价值的转化长期存在且未解决的胺和有机硼限制。
• Fluorescent Discrimination between Traces of Chemical Warfare Agents and Their Mimics
  作者：Borja Díaz de Greñu、Daniel Moreno、Tomás Torroba、Alexander Berg、Johan Gunnars、Tobias Nilsson、Rasmus Nyman、Milton Persson、Johannes Pettersson、Ida Eklind、Pär Wästerby

  DOI：10.1021/ja500710m

  日期：2014.3.19

  array of fluorogenic probes is able to discriminate between nerve agents, sarin, soman, tabun, VX and their mimics, in water or organic solvent, by qualitative fluorescence patterns and quantitative multivariate analysis, thus making the system suitable for the in-the-field detection of traces of chemical warfare agents as well as to differentiate between the real nerve agents and other related compounds

  一系列荧光探针能够通过定性荧光模式和定量多变量分析区分水或有机溶剂中的神经毒剂、沙林、梭曼、塔崩、VX 及其模拟物，从而使该系统适用于现场检测化学战剂的痕迹以及区分真正的神经毒剂和其他相关化合物。
• [EN] PLATELET-ACTIVATING FACTOR RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DES RÉCEPTEURS DU FACTEUR D'ACTIVATION PLAQUETTAIRE
  申请人：MERCK SHARP & DOHME

  公开号：WO2011005608A1

  公开（公告）日：2011-01-13

  Cyclohexyl sulfonamide compounds which are platelet-activating factor (PAF) receptor antagonists. Said compounds may be useful, for example, for the treatment of atherosclerosis or other PAF-mediated disorders, including inflammatory, cardiovascular, and immune disorders.

  环己基磺胺化合物是血小板活化因子（PAF）受体拮抗剂。这些化合物可能对治疗动脉粥样硬化或其他PAF介导的疾病有用，包括炎症性、心血管和免疫性疾病。
• Site-Selective CH Borylation of Quinolines at the C8 Position Catalyzed by a Silica-Supported Phosphane-Iridium System
  作者：Shota Konishi、Soichiro Kawamorita、Tomohiro Iwai、Patrick G. Steel、Todd B. Marder、Masaya Sawamura

  DOI：10.1002/asia.201301423

  日期：2014.2

  Site‐selective CH borylation of quinoline derivatives at the C8 position has been achieved by using a heterogeneous Ir catalyst system based on a silica‐supported cage‐type monophosphane ligand SMAP. The efficient synthesis of a corticotropin‐releasing factor1 (CRF1) receptor antagonist based on a late‐stage CH borylation strategy demonstrates the utility of the C8 borylation reaction.

  位点选择性Ç  H在C8位置喹啉衍生物的硼基化已经通过使用基于二氧化硅负载笼型monophosphane配体SMAP非均相铱催化剂系统来实现。促肾上腺皮质激素释放因子的有效合成1（CRF 1）受体基于后期阶段C拮抗剂 ħ硼化策略演示C8硼化反应的效用。