2,5-双(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)呋喃 | 476004-83-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 中文名称: 2,5-双(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)呋喃
• 中文别名: 呋喃-2,5-二硼酸频哪醇酯
• 英文名称: 2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan
• 英文别名: Furan-2,5-diboronic acid, pinacol ester；4,4,5,5-tetramethyl-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-yl]-1,3,2-dioxaborolane
• CAS: 476004-83-8
• 化学式: C₁₆H₂₆B₂O₅
• 分子量: 320.001
• InChiKey: FOQCCZCSUIHXCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  50.1
• 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: Furan-2,5-diboronic acid, pinacol ester
Synonyms: 2,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan

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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: Furan-2,5-diboronic acid, pinacol ester
CAS number: 476004-83-8

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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: C16H26B2O5
Molecular weight: 320.0

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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：

  [双(三氟乙酰氧基)碘]苯 、 2,5-双(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)呋喃 在 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以80%的产率得到phenyl(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-yl)iodonium trifluoroacetate
  参考文献：
  名称：

  硼取代的二芳基碘鎓盐的合成及选择性转化为功能化的芳基硼酸酯

  摘要：

  休眠硼正等待由芳基硼酸酯衍生物合成的二芳基碘鎓盐的真实命运，这是根据两种替代的通用方法，使用高价碘（III）试剂和氟代醇溶剂：芳基CH键的转化和硼-碘（III）的交换（参见方案） ； FG =官能团）。可以通过无催化剂和金属催化的反应来使盐官能化，而不会丧失硼的官能度。

  DOI：

  10.1002/anie.201206917
• 作为产物：
  描述：

  呋喃 、 频那醇硼烷 在 C₃₉H₅₉Br₂CoN₇Si₂ 、 三乙基硼氢化钠 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 2,5-双(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)呋喃
  参考文献：
  名称：

  钴催化的芳烃区域选择性硼化：N-杂环亚甲硅烷基在金属介导的C-H键活化中作为电子给体

  摘要：

  由于芳烃的原子经济性和硼酸盐化产物在增值合成中的广泛应用，近年来，芳烃的CH硼化已引起人们极大的兴趣。合成了一种新的带有双（N-杂环甲硅烷基）-吡啶钳式配体（SiNSi）的双（甲硅烷基）钴（II）配合物，并对其结构进行了表征。它使吡啶，呋喃和氟化芳烃的区域选择性催化CH硼化成为可能。值得注意的是，与以前已知的催化体系相比，它对氟化芳烃的硼化具有互补的区域选择性，这表明N杂环亚甲硅烷基供体在金属催化的催化应用中具有巨大的潜力。

  DOI：

  10.1002/chem.201605937

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。
• <i>Ortho</i>-Selective C–H Borylation of Aromatic Ethers with Pinacol-borane by Organo Rare-Earth Catalysts
  作者：Can Xue、Yong Luo、Huailong Teng、Yuanhong Ma、Masayoshi Nishiura、Zhaomin Hou

  DOI：10.1021/acscatal.8b01364

  日期：2018.6.1

  borylation of aromatic ethers such as anisoles is of much interest and importance, but has remained a challenge to date. We report herein the catalytic ortho-selective C–H borylation of a wide range of aromatic ethers with pinacolborane (HBpin) by rare-earth metallocene complexes. This protocol offers an efficient and straightforward route for the synthesis of a variety of borylated aromatic ether derivatives

  芳族醚（如茴香醚）的区域选择性C–H硼化非常令人关注和重要，但迄今为止仍是一个挑战。我们在这里报告了稀土金属茂配合物与频哪醇硼烷（HBpin）催化的各种芳族醚的邻位选择性C–H硼化反应。该方案为合成各种硼酸化的芳族醚衍生物提供了一种有效而直接的途径。发现用于稀土金属催化剂的合适的金属/配体组合对于促进这种转化至关重要。
• Iridium-catalyzed C–H coupling reaction of heteroaromatic compounds with bis(pinacolato)diboron: regioselective synthesis of heteroarylboronates
  作者：Jun Takagi、Kazuaki Sato、John F Hartwig、Tatsuo Ishiyama、Norio Miyaura

  DOI：10.1016/s0040-4039(02)01135-8

  日期：2002.8

  The C–H coupling of aromatic heterocycles with bis(pinacolato)diboron was carried out in octane at 80–100°C in the presence of a 1/2[IrCl(COD)]2-(4,4′-di-tert-butyl-2,2′-bipyridine) catalyst (3 mol%). The reactions of five-membered substrates such as thiophene, furan, pyrrole, and their benzo-fused derivatives exclusively produced 2-borylated products, whereas those of six-membered heterocycles including

  芳香族杂环与双（频哪醇）二硼烷的C–H偶联是在80–100°C的辛烷中，在存在1/2 [IrCl（COD）] 2-（4,4'-二酯的条件下进行的-2，2'-联吡啶-丁基）催化剂（3mol％）。五元底物（例如噻吩，呋喃，吡咯及其苯并稠合衍生物）的反应仅生成2硼化产物，而六元杂环（包括吡啶和喹啉）的反应则选择性地在3位发生。还通过使用几乎等摩尔量的底物和二硼来实现双（硼基）杂芳族化合物的区域选择性合成。
• Mechanism of the Mild Functionalization of Arenes by Diboron Reagents Catalyzed by Iridium Complexes. Intermediacy and Chemistry of Bipyridine-Ligated Iridium Trisboryl Complexes
  作者：Timothy M. Boller、Jaclyn M. Murphy、Marko Hapke、Tatsuo Ishiyama、Norio Miyaura、John F. Hartwig

  DOI：10.1021/ja053433g

  日期：2005.10.1

  electron-poor arenes than with electron-rich arenes. However, both the stoichiometric and catalytic reactions also occur faster with the electron-rich heteroarenes thiophene and furan than with arenes, perhaps because eta(2)-heteroarene complexes are more stable than the eta(2)-arene complexes and the eta(2)-heteroarene or arene complexes are intermediates that precede oxidative addition. Kinetic studies on the

  本文描述了芳烃与二硼试剂 B(2)pin(2)（双频哪醇二硼烷（4））在 4,4'-二叔丁基联吡啶 (dtbpy) 和烯烃连接的卤化铱或烯烃连接的铱醇盐配合物。这项工作将催化剂静止状态确定为 [Ir(dtbpy)(COE)(Bpin)(3)]（COE = 环辛烯，Bpin = 4,4,5,5-四甲基-1,3,2-二氧杂环戊二烯基）。[Ir(dtbpy)(COE)(Bpin)(3)] 由 [Ir(COD)(OMe)](2)、dtbpy、COE 和 HBpin 通过独立合成以高产率制备。这种复合物是由 [Ir(COD)(OMe)](2)、dtbpy、COE 和 B(2)pin(2) 以低产率形成的。动力学研究表明，该复合物在 COE 可逆解离后与芳烃反应。在 COE 解离和 B(2)pin(2) 的还原消除后，芳烃与 Ir(I) 复合物 [Ir(dtbpy)Bpin] 反应的另一种机制不会发生
• Iron-Catalysed C(sp2)-H Borylation Enabled by Carboxylate Activation
  作者：Luke Britton、Jamie H. Docherty、Andrew P. Dominey、Stephen P. Thomas

  DOI：10.3390/molecules25040905

  日期：——

  Arene C(sp2)-H bond borylation reactions provide rapid and efficient routes to synthetically versatile boronic esters. While iridium catalysts are well established for this reaction, the discovery and development of methods using Earth-abundant alternatives is limited to just a few examples. Applying an in situ catalyst activation method using air-stable and easily handed reagents, the iron-catalysed

  芳烃 C(sp2)-H 键硼化反应为合成多功能硼酸酯提供了快速有效的途径。虽然铱催化剂已经很好地用于该反应，但使用地球上丰富的替代品的方法的发现和开发仅限于几个例子。应用使用空气稳定且易于处理的试剂的原位催化剂活化方法，已开发出铁催化的呋喃和噻吩在蓝光照射下的 C(sp2)-H 硼酸化反应。已经制备并表征了关键的反应中间体，并表明两种机制途径都在起作用，涉及 CH 金属化和铁硼化物的形成。