5-甲氧羰基-呋喃-2-硼酸频哪醇酯 | 676501-87-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: 5-甲氧羰基-呋喃-2-硼酸频哪醇酯
• 英文名称: methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carboxylate
• CAS: 676501-87-4
• 化学式: C₁₂H₁₇BO₅
• 分子量: 252.075
• InChiKey: HHXRIHYFWBIMFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-(Methoxycarbonyl)furan-2-boronic acid pinacol ester
Synonyms: Methyl 5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-furan-2-carboxylate

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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: 5-(Methoxycarbonyl)furan-2-boronic acid pinacol ester
CAS number: 676501-87-4

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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: C12H17BO5
Molecular weight: 252.1

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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：

  5-甲氧羰基-呋喃-2-硼酸频哪醇酯 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 tripotassium phosphate "n" hydrate 、 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成
  参考文献：
  名称：

  Discovery of imidazo[1,2-b]pyridazines as IKKβ inhibitors. Part 3: Exploration of effective compounds in arthritis models

  摘要：

  We have discovered imidazo[1,2-b]pyridazine derivatives that show suppressive activity of inflammation in arthritis models. We optimized the substructures of imidazo[1,2-b] pyridazine derivatives to combine potent IKK beta inhibitory activity, TNF alpha inhibitory activity in vivo and excellent pharmacokinetics. The compound we have acquired, which had both potent activities and good pharmacokinetic profiles based on improved physicochemical properties, demonstrated efficacy on collagen-induced arthritis models in mice and rats. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.115
• 作为产物：
  描述：

  5-溴-2-糠酸甲酯 、 联硼酸频那醇酯 在 N,N’-bis(octadecyl)-L-Boc-glutamic diamide 、 N,N-二异丙基乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 22.0h， 以51%的产率得到5-甲氧羰基-呋喃-2-硼酸频哪醇酯
  参考文献：
  名称：

  凝胶纳米反应器中杂芳烃的需氧可见光驱动硼酸化

  摘要：

  杂芳烃硼酸酯是现代有机合成中有价值的中间体。作为积木，它们可以进一步应用于新材料的合成，因为它们可以很容易地转化为任何其他官能团。显然需要努力为它们的制备提供新颖和有效的策略。在这里，我们在易于使用的凝胶纳米反应器中在非常温和的条件下实现了市售杂芳烃卤化物的硼化。它在室温下在无光催化剂和有氧条件下使用可见光作为能源，使该协议非常有吸引力。凝胶网络提供了足够的稳定微环境以支持广泛的底物范围，包括呋喃、噻吩、硒酚和吡咯硼酸酯。

  DOI：

  10.1021/acs.orglett.1c00451

文献信息

• [EN] BASE METAL CATALYZED BORYLATION OF ARENES AND AROMMATIC HETEROCYCLES<br/>[FR] BORYLATION D'ARÈNES ET D'HÉTÉROCYCLES AROMATIQUES CATALYSÉE PAR UN MÉTAL DE BASE
  申请人：UNIV PRINCETON

  公开号：WO2015089119A1

  公开（公告）日：2015-06-18

  In one aspect, cobalt complexes are described herein. In some embodiments, such cobalt complexes employ bis(phosphine) or bis(imine) ligand and are operable as catalysts for borylation of arenes and aromatic heterocycles.

  在某些方面，本文描述了钴络合物。在某些实施例中，这样的钴络合物使用双(膦)或双(亚胺)配体，并且可作为芳烃和芳香杂环的硼化催化剂。
• 五元杂环类衍生物及其制备方法和其在医药上的用途
  申请人：浙江海正药业股份有限公司

  公开号：CN110294745B

  公开（公告）日：2022-04-19

  本发明提供了一种通式(I)所示的五元杂环类衍生物或其药学上可接受的盐、及其制备方法，以及它们作为治疗剂，特别是作为选择性转染期间重排(RET)激酶抑制剂的用途。其中通式(I)中的A，B，C，D，E，X，R1，R2，R3的定义与说明书中的定义相同。
• Iridium(I)‐Catalyzed C−H Borylation in Air by Using Mechanochemistry
  作者：Yadong Pang、Tatsuo Ishiyama、Koji Kubota、Hajime Ito

  DOI：10.1002/chem.201900685

  日期：2019.3.27

  the first time to an iridium(I)‐catalyzed C−H borylation reaction. By using either none or just a catalytic amount of a liquid, the mechanochemical C−H borylation of a series of heteroaromatic compounds proceeded in air to afford the corresponding arylboronates in good‐to‐excellent yields. A one‐pot mechanochemical C−H borylation/Suzuki–Miyaura cross‐coupling sequence for the direct synthesis of 2‐aryl

  机械化学已首次应用于铱（I）催化的CH硼酸酯化反应。通过不使用或仅使用催化量的液体，一系列杂芳族化合物的机械化学CH硼化在空气中进行，从而以优异的产率获得了相应的芳基硼酸酯。还描述了直接合成2-芳基吲哚衍生物的一锅机械化学CH硼化/ Suzuki-Miyaura交叉偶联序列。这项研究是发展工业上有吸引力的无溶剂CH键在空气中的功能化过程的重要里程碑。
• Iridium–bipyridine periodic mesoporous organosilica catalyzed direct C–H borylation using a pinacolborane
  作者：Yoshifumi Maegawa、Shinji Inagaki

  DOI：10.1039/c5dt00239g

  日期：——

  organosilica containing bipyridine ligands within the framework (Ir-BPy-PMO) and pinacolborane (HBpin) is reported. Ir-BPy-PMO showed higher catalytic activity toward the borylation of benzene with inexpensive HBpin compared to expensive bis(pinacolato)diboron (B2pin2). The precatalyst could be handled without the use of a glove box. The catalyst was easily recovered from reaction mixtures by simple filtration

  据报道，铱（Ir）络合物固定在骨架（Ir-BPy-PMO）和吡萘甲硼烷（HBpin）内的含联吡啶配体的周期性介孔有机二氧化硅上，铱和铱的混合直接异构化催化芳烃和杂芳烃的非均相催化。Ir-BPy-PMO与便宜的bis（pinacolato）diboron（B 2 pin 2）相比，对便宜的HBpin苯的硼化反应显示出更高的催化活性。）。无需使用手套箱即可处理预催化剂。通过在空气中简单过滤，可以容易地从反应混合物中回收催化剂。回收的催化剂对于苯的硼酸酯化反应仍显示出至少三倍以上的良好催化活性。使用HBpin通过Ir-BPy-PMO成功地以高硼效率将各种芳烃和杂芳烃进行了硼化，而对于某些杂芳烃与B 2 pin 2进行的硼化却几乎没有观察到活性。。使用Ir-BPy-PMO和HBpin的系统还用于合成多硼化的基于噻吩的积木，其中包含梯形，并苯并噻吩和聚并噻吩骨架。稳定且可重复使用的固体催化剂与廉价的
• 一种高效催化五元杂环选择性发生硼化反应的方法
  申请人：台州学院

  公开号：CN111039967A

  公开（公告）日：2020-04-21

  本发明涉及一种高效催化五元杂环选择性发生硼化反应的方法。顺利实现以廉价的钌金属的络合物为催化剂，在温和条件下即可方便地催化呋喃、噻吩衍生物与廉价易得的有机硼试剂发生选择性硼化反应来制备杂环硼酸酯产物。与已报道方法相比，该方法具备反应选择性专一、催化剂用量低、操作便捷、不需要添加反应溶剂等明显优势，为杂环硼酸酯产物的实验室制备或工业生产提供了一种高效、高选择性的反应策略。