4-(9H-咔唑-9-基)苯硼酸 | 419536-33-7

• 物质功能分类: 医药中间体 - OLED材料中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 4-(9H-咔唑-9-基)苯硼酸
• 中文别名: 4-(9-咔唑基)苯硼酸；B-[4-(9H-咔唑-9-基)苯基]硼酸；4-(9H-咔唑)苯硼酸；4-(9-咔唑基)苯基硼酸
• 英文名称: 4-(carbazol-9-yl)phenylboronic acid
• 英文别名: 4-(9H-carbazol-9-yl)phenylboronic acid；4-(9-carbazolyl)phenylboronic acid；4-(9H-carbazol-9-yl)benzeneboronic acid；4-(N-carbazolyl)phenylboronic acid；4-(9H-carbazole-9-yl)phenylboronic acid；4-(9H-carbazolyl)phenyl-boronic acid；4-(9-carbazolyl)benzeneboronic acid；4-(N-carbazolyl)benzeneboronic acid；4-(9-carbazole)phenylboronic acid；4-carbazolyl-1-phenylboronic acid；4-(9H-carbozol-9-yl)phenylboronic acid；9H-carbazole-9-(4-phenyl)boronic acid；4-(carbazol-9-yl)benzeneboronic acid；4-(carbazole-9-yl)phenylboronic acid；(4-(9H-Carbazol-9-yl)phenyl)boronic acid；(4-carbazol-9-ylphenyl)boronic acid
• CAS: 419536-33-7
• 化学式: C₁₈H₁₄BNO₂
• 分子量: 287.126
• InChiKey: JGAVTCVHDMOQTJ-UHFFFAOYSA-N

物化性质

• 熔点：
  264°C(lit.)
• 沸点：
  452.7±51.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.4
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P305+P351+P338,P304+P340,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温且干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(9H-Carbozol-9-yl)phenylboronic 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-(9H-Carbozol-9-yl)phenylboronic acid
CAS number: 419536-33-7

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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.
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: C18H14BNO2
Molecular weight: 287.1

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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, nitrogen 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：

  4-(9H-咔唑-9-基)苯硼酸 在 aluminum (III) chloride 、 四(三苯基膦)钯 、 potassium fluoride dihydrate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 12.5h， 生成 N-(7-溴-9,9-二甲基芴-2-基)咔唑
  参考文献：
  名称：

  光电材料中间体N-(7-溴-9,9-二甲基芴-2-基）咔唑的合成方法

  摘要：

  本发明属于有机合成领域，涉及光电材料中间体N‑(7‑溴‑9，9‑二甲基芴‑2‑基）咔唑的合成。该方法将4‑咔唑基苯硼酸和5‑溴‑2‑碘苯甲酸甲酯偶联，再用格氏试剂生成甲基化产物，最后用三氯化铝傅克反应关环，得到目标产物。该方法通过降低反应温度，提高溴碘的选择性，提高了纯度和收率，收率达87%以上。降低了成本，适合工业化化生产。

  公开号：

  CN112194612A
• 作为产物：
  描述：

  9-(4-溴苯基)咔唑 在 正丁基锂 、 硼酸三甲酯 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 以88.4%的产率得到4-(9H-咔唑-9-基)苯硼酸
  参考文献：
  名称：

  Novel multifunctional organic semiconductor materials based on 4,8-substituted 1,5-naphthyridine: synthesis, single crystal structures, opto-electrical properties and quantum chemistry calculation

  摘要：

  一系列4,8取代的1,5-萘啶（1a–1h）已成功合成，通过4,8-二溴-1,5-萘啶（4）与相应的硼酸（2a–2h）在催化性醋酸钯的存在下进行铃木交叉偶联反应，收率为41.4%–75.8%，并得到良好表征。它们在热稳定性方面表现优异，具有高相变温度（高于186°C）。化合物1b、1e和1f分别在单斜晶系中结晶，空间群为P21/c、P21/c和P21/n。所有化合物表现出最低能量吸收带（λmaxAbs: 294–320 nm），揭示了较低的光学带隙（2.77–3.79 eV）。这些材料在二氯甲烷稀溶液中发出蓝色荧光，λmaxEm范围为434–521 nm，在固态中为400–501 nm。4,8取代的1,5-萘啶1a–1h的估计电子亲合能（EA）为2.38–2.72 eV，适合用作电子传输材料，而离子化势（IP）为4.85–5.04 eV，促进了优良的孔注入/孔传输材料特性。使用DFT B3LYP/6-31G*进行的量子化学计算显示，最低未占分子轨道（LUMO）几乎相同，范围为−2.39至−2.19 eV，最高占分子轨道（HOMO）范围为−5.33至−6.84 eV。这些结果表明，具有简单结构的4,8取代1,5-萘啶1a–1h可能是开发高效OLED的有希望的蓝色发射（或蓝绿色发射）材料、电子传输材料以及孔注入/孔传输材料。

  DOI：

  10.1039/c2ob25926e
• 作为试剂：
  描述：

  9-(4-溴苯基)咔唑 、 n-butyllithium hexane 、 硼酸三甲酯 、 盐酸 在 氮气 、 乙酸乙酯 、 Brine 、 magnesium sulfate 、 氯仿 、 正己烷 、 white powder 、 4-(9H-咔唑-9-基)苯硼酸 作用下， 以 四氢呋喃 为溶剂， 反应 28.0h， 以was obtained in yield 58%的产率得到4-(9H-咔唑-9-基)苯硼酸
  参考文献：
  名称：

  Anthracene Derivatives and Light-Emitting Devices Using the Anthracene Derivatives

  摘要：

  本发明提供了新型蒽衍生物。特别地，本发明提供具有高发光效率的发光元件和具有长寿命的发光元件。此外，本发明通过使用这些发光元件，提供了具有长寿命的发光器件和电子器件。提供了由通式（1）表示的蒽衍生物。此外，由于通式（1）表示的蒽衍生物具有高发光效率，因此使用该蒽衍生物的发光元件也可以具有高发光效率。通过使用通式（1）表示的蒽衍生物，可以提供具有长寿命的发光元件。

  公开号：

  US20090004506A1

文献信息

• NiH‐Catalyzed Migratory Defluorinative Olefin Cross‐Coupling: Trifluoromethyl‐Substituted Alkenes as Acceptor Olefins to Form <i>gem</i> ‐Difluoroalkenes
  作者：Fenglin Chen、Xianfeng Xu、Yuli He、Genping Huang、Shaolin Zhu

  DOI：10.1002/anie.201915840

  日期：2020.3.23

  a NiH-catalyzed migratory defluorinative coupling between two electronically differentiated olefins. A broad range of unactivated donor olefins can be joined directly to acceptor olefins containing an electron-deficient trifluoromethyl substituent in both intra- and intermolecular fashion to form gem-difluoroalkenes. This migratory coupling shows both site- and chemoselectivity under mild conditions

  我们报告了两个电子分化的烯烃之间的镍氢催化迁移脱氟偶联。多种未活化的供体烯烃可以以分子内和分子间方式直接与含有缺电子的三氟甲基取代基的受体烯烃键合，形成宝石-二氟烯烃。这种迁移偶联在温和条件下显示出位选择性和化学选择性，并形成了叔碳或季碳中心。
• 화합물, 이를 포함하는 유기 광전자 소자 및 표시장치
  申请人：CHEIL INDUSTRIES INC. 제일모직주식회사(119980034532) Corp. No ▼ 170111-0000076BRN ▼504-81-00025

  公开号：KR20150130221A

  公开（公告）日：2015-11-23

  하기 화학식 1로 표시되는 화합물, 이를 포함하는 유기 광전자 소자 및 상기 유기 광전자 소자를 포함하는 표시장치에 관한 것이다. [화학식 1] 상기 화학식 1에서, L 내지 L, R 내지 R의 정의는 명세서에 정의된 바와 같다.

  这个化合物被表示为化学式1，涉及包含该化合物的有机光电器件以及包含该有机光电器件的显示装置。在化学式1中，L至L，R至R的定义如规范中所定义。
• Palladium-catalyzed Suzuki–Miyaura reaction of fluorinated vinyl chloride: a new approach for synthesis α and α,β-trifluoromethylstyrenes
  作者：Yang Li、Bo Zhao、Kun Dai、Dong-Huai Tu、Bo Wang、Yao-Yu Wang、Zhao-Tie Liu、Zhong-Wen Liu、Jian Lu

  DOI：10.1016/j.tet.2016.07.085

  日期：2016.9

  A mild and efficient palladium-catalyzed cross-coupling between fluorinated vinyl chloride and arylboronic acids is described. The use of ligand B successfully overcomes the strong electronic withdrawing of trifluoromethylated substrates and allows the efficient synthesis of a wide range of α and α,β-trifluoromethyl containing olefins. By using this method, the key intermediate for synthesis of Efavirenz

  描述了氟化氯乙烯与芳基硼酸之间温和有效的钯催化的交叉偶联。配体B的使用成功地克服了三氟甲基化底物的强电子吸出，并允许有效合成范围广泛的含α和α，β-三氟甲基的烯烃。通过这种方法，可以通过简单的途径获得合成依非韦伦的关键中间体。将两个氟利昂分子有效转化为有用的含α和α，β-三氟甲基的烯烃是有机化学中的有用途径。
• Oxidative Heck Reaction of Fluorinated Olefins with Arylboronic Acids by Palladium Catalysis
  作者：Yang Li、Dong-Huai Tu、Yu-Jie Gu、Bo Wang、Yao-Yu Wang、Zhao-Tie Liu、Zhong-Wen Liu、Jian Lu

  DOI：10.1002/ejoc.201500597

  日期：2015.7

  The palladium-catalyzed oxidative Heck reaction of 2,3,3,3-tetrafluoroprop-1-ene with various arylboronic acids was explored for the first time. This method provides a direct route to access (Z)-β-fluoro-β-(trifluoromethyl)styrenes with high stereoselectivity.

  首次探索了钯催化的 2,3,3,3-四氟丙-1-烯与各种芳基硼酸的氧化 Heck 反应。该方法提供了获得具有高立体选择性的 (Z)-β-氟-β-(三氟甲基)苯乙烯的直接途径。
• Promoting charge separation in donor–acceptor conjugated microporous polymers <i>via</i> cyanation for the photocatalytic reductive dehalogenation of chlorides
  作者：Weijie Zhang、Jiyong Deng、Zhengjun Fang、Donghui Lan、Yunfeng Liao、Xiang Zhou、Qingquan Liu

  DOI：10.1039/d1cy01386f

  日期：——

  Conjugated microporous polymers (CMPs) have emerged as promising heterogeneous photocatalysts for organic transformations owing to their structural designability and functional versatility. However, limited by the insufficient separation of the photo-generated excitons, their photocatalytic efficiency falls far short of expectations. Herein, we demonstrate a cyanation strategy to promote charge carrier

  共轭微孔聚合物（CMPs）由于其结构可设计性和功能多功能性，已成为有前途的有机转化多相光催化剂。然而，受光生激子分离不充分的限制，其光催化效率远低于预期。在此，我们展示了一种氰化策略，通过选择性地将咔唑和氰基分别作为供电子和吸电子单元来促进 CMP 中的电荷载流子分离。由此产生的 CMP 具有 π 扩展的供体 (D)-受体 (A) 共轭结构，赋予它们独特的半导体特性，其中促进了有效的电荷分离和转移以及广泛的可见光吸收。与无氰对应物相比，氰基官能化的 CMP 显示出优异的光催化效率，例如氯化物的光催化还原脱卤。更突出的是，所设计的 CMP 的完全可回收性以及至少 10 次运行的催化活性而不会损失在氯化物的光催化还原脱卤中的催化性能，这证明了它们的稳健性和可持续性。

表征谱图