5-溴噻吩-2-硼酸频哪醇酯 | 676501-84-1

• 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 - 噻吩类
• 中文名称: 5-溴噻吩-2-硼酸频哪醇酯
• 中文别名: 2-溴噻吩-5-硼酸频那醇酯；5-溴噻吩-2-硼酸频那醇酯
• 英文名称: 2-(5-bromothiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 676501-84-1
• 化学式: C₁₀H₁₄BBrO₂S
• 分子量: 289.001
• InChiKey: QRTVEZRHUSSDCW-UHFFFAOYSA-N

物化性质

• 沸点：
  332.0±27.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Bromothiophene-2-boronic acid pinacol ester
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: 5-Bromothiophene-2-boronic acid pinacol ester
CAS number: 676501-84-1

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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: C10H14BBrO2S
Molecular weight: 289.0

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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, hydrogen bromide, sulfur oxides.

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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-溴噻吩-2-硼酸频哪醇酯 在 4,4'-联吡啶 、 氧气 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以0.097 g的产率得到5,5'-二溴-2,2'-联噻吩
  参考文献：
  名称：

  经由CH硼化的芳烃立体控制CH / CH均偶联。

  摘要：

  描述了一种温和的一锅法方案，该方案通过顺序的Ir催化的CH硼酸酯化和Cu催化的芳烃均偶联合成对称的联芳基。所形成的联芳基的区域化学空间上受CH硼酸酯化步骤的控制。该方法还成功地扩展到了杂芳烃。通过这种方法获得的某些产品无法通过Ullmann或Suzuki耦合协议获得。最后，我们显示了一锅序列描述了CH硼化/ Cu催化的均偶联/ Pd催化的Suzuki偶联以获得π扩展的芳烃骨架。

  DOI：

  10.1039/c9ob00995g
• 作为产物：
  描述：

  噻吩-2-硼酸频哪醇酯 在 gold(III) chloride 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以25%的产率得到5-溴噻吩-2-硼酸频哪醇酯
  参考文献：
  名称：

  金（III）芳香族硼酸酯的催化的卤化与Ñ -Halosuccinimides

  摘要：

  芳环上带有卤素取代基的芳族硼酸酯可通过AuCl 3催化的N-卤代琥珀酰亚胺的卤化反应合成。

  DOI：

  10.1021/ol102350v

文献信息

• Chemoselective Rhodium-Catalyzed Borylation of Bromoiodoarenes Under Mild Conditions
  作者：Anthony J. Varni、Michael V. Bautista、Kevin J.T. Noonan

  DOI：10.1021/acs.joc.0c00178

  日期：2020.5.15

  developed for the preparation of aryl boronate esters. The reaction proceeds under mild conditions with excellent selectivity for C-I bonds in bromoiodoarenes and exhibits broad functional group tolerance. This procedure can act as a complementary approach toward bifunctional arenes along with other metal-catalyzed borylations. Additionally, the reaction's utility in the preparation of monomers for metal-catalyzed

  已经开发了化学选择性的铑催化的硼化来制备芳基硼酸酯。该反应在温和的条件下进行，对溴代碘代芳烃中的CI键具有出色的选择性，并且具有宽泛的官能团耐受性。该方法可以作为双官能团与其他金属催化的硼烷基化反应的补充方法。另外，证明了该反应在制备用于金属催化的交叉偶联聚合的单体中的效用。
• Double N,B-Type Bidentate Boryl Ligands Enabling a Highly Active Iridium Catalyst for C–H Borylation
  作者：Guanghui Wang、Liang Xu、Pengfei Li

  DOI：10.1021/jacs.5b05252

  日期：2015.7.1

  promise in catalysis due to their very high electron-donating property. In this communication double N,B-type boryl anions were designed as bidentate ligands to promote an sp(2) C-H borylation reaction. A symmetric pyridine-containing tetraaminodiborane(4) compound (1) was readily prepared as the ligand precursor that could be used, in combination with [Ir(OMe)(COD)]2, to in situ generate a highly active

  硼酸配体由于其非常高的给电子特性而在催化中具有前景。在此通信中，双 N、B 型硼酸阴离子被设计为双齿配体以促进 sp(2) CH 硼酸化反应。含有对称吡啶的四氨基二硼烷 (4) 化合物 (1) 很容易制备为配体前体，可与 [Ir(OMe)(COD)]2 结合使用，原位生成高活性催化剂，用于广泛的应用。一系列（杂）芳烃底物，包括高度富电子和/或空间位阻的底物。这项工作提供了支持均相有机金属催化的双齿硼基配体的第一个例子。
• Flow synthesis of arylboronic esters bearing electrophilic functional groups and space integration with Suzuki–Miyaura coupling without intentionally added base
  作者：Aiichiro Nagaki、Yuya Moriwaki、Jun-ichi Yoshida

  DOI：10.1039/c2cc36197c

  日期：——

  We found that an integrated flow microreactor system enables the preparation of boronic esters bearing electrophilic functional groups using organolithium chemistry and that it allows for their use in Suzuki-Miyaura cross-coupling without intentionally added base. Based on this method, cross-coupling of two aryl halides bearing electrophilic functional groups was accomplished to obtain the corresponding

  我们发现，集成的流动微反应器系统能够使用有机锂化学方法制备带有亲电官能团的硼酸酯，并且可以将其用于Suzuki-Miyaura交叉偶联中而无需故意添加碱。基于此方法，完成了两个带有亲电官能团的芳基卤化物的交叉偶联，以一次获得相应的联芳基化合物。
• Iridium-Catalyzed Direct Borylation of Five-Membered Heteroarenes by Bis(pinacolato)diboron: Regioselective, Stoichiometric, and Room Temperature Reactions
  作者：Tatsuo Ishiyama、Jun Takagi、Yuhei Yonekawa、John F. Hartwig、Norio Miyaura

  DOI：10.1002/adsc.200303058

  日期：2003.9

  and pyrroles in stoichiometric amounts relative to bis(pinacolato)diboron in hexane at room temperature. The heteroarylboronates from regioselective CH activation at the 5-position were formed in high yields. Similar borylations of unsubstituted heteroarenes with an equimolar amount of the diboron regioselectively provided 2,5-bis(boryl)heteroarenes.

  由1/2 [Ir（OMe）（COD）] 2和4,4'-二叔丁基-2,2'-联吡啶生成的铱（I）络合物催化2-取代的噻吩，呋喃的直接硼化反应在室温下，相对于己烷中双（频哪醇）二硼的化学计量的吡咯和吡咯。高产率地形成了由5-位区域选择性CH活化引起的杂芳基硼酸酯。用等摩尔量的二硼区域选择性地提供未取代的杂芳烃的类似硼烷基化，选择性地提供了2，5-双（硼基）杂芳烃。
• Rh^III-Catalyzed Direct Heteroarylation of C(sp³)–H and C(sp²)–H Bonds in Heterocycles with <i>N</i>-Heteroaromatic Boronates
  作者：Huai-Wei Wang、Jia-Xue Wu、Yu-Han Qiao、Yong-Fei Li、Da-Cheng Li、Jian-Min Dou、Qing-Xia Yao、Yi Lu

  DOI：10.1021/acs.orglett.1c02546

  日期：2021.9.17

  Herein, we disclose a RhIII-catalyzed heteroarylation of C(sp3)–H and C(sp2)–H bonds in heterocycles with organoboron reagents. This protocol displays high efficiency and excellent functional group tolerance. A range of heterocyclic boronates with strong coordinating atoms, including pyridine, pyrimidine, pyrazole, thiophene, and furan derivatives, can be extensively served as the coupling reagents

  在此，我们公开了用有机硼试剂使杂环中的 C(sp 3 )-H 和 C(sp 2 )-H 键发生 Rh III催化的杂芳基化反应。该协议显示出高效率和出色的官能团耐受性。一系列具有强配位原子的杂环硼酸酯，包括吡啶、嘧啶、吡唑、噻吩和呋喃衍生物，可广泛用作偶联剂。直接杂芳基化方法可以在合成具有多个杂环的药物分子方面提供潜在的应用。