2,4-二氯苯硼酸频那醇酯 | 68716-50-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,4-二氯苯硼酸频那醇酯
• 英文名称: 2-(2,4-dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 68716-50-7
• 化学式: C₁₂H₁₅BCl₂O₂
• 分子量: 272.967
• InChiKey: SMSBTAPKLZZTAU-UHFFFAOYSA-N

物化性质

• 沸点：
  339.1±32.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

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
• 储存条件：
  储存条件：干燥、密封，并在2-8℃下保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2,4-Dichlorophenylboronic acid, pinacol ester
Synonyms: 2-(2,4-Dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
May cause long lasting harmful effects to aquatic life
H413:

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Section 3. Composition/information on ingredients.
Ingredient name: 2,4-Dichlorophenylboronic acid, pinacol ester
CAS number: 68716-50-7

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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.
Storage: Store in closed vessels, refrigerated.

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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
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C12H15BCl2O2
Molecular weight: 273.0

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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 chloride.

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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：

  2,4-二氯苯硼酸频那醇酯 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 23.0h， 以69%的产率得到2,4-二氯酚
  参考文献：
  名称：

  A mild conversion of arylboronic acids and their pinacolyl boronate esters into phenols using hydroxylamine

  摘要：

  Hydroxylamine was found to be a mild reagent for conversion of arylboronic acids and their pinacolyl boronate esters into phenols. This procedure works on most arylboronic acids at room temperature, yielding phenols in moderate to good yields, and efficiently on arylboronates also yielding phenols in good yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.02.069
• 作为产物：
  描述：

  1,3-二氯苯 在 aluminum (III) chloride 、 三乙胺 作用下， 以 氘代二甲亚砜 、 二氯甲烷 为溶剂， 反应 54.0h， 生成 2,4-二氯苯硼酸频那醇酯
  参考文献：
  名称：

  卤代芳烃的区域选择性亲电硼化。

  摘要：

  卤代芳烃使用胺：BCl3：AlCl3以1：1：2的比例进行直接硼化。酯化后，频哪醇硼酸酯以良好的收率被分离，其区域选择性受空间和电子效应控制。

  DOI：

  10.1039/c4cc10153g

文献信息

• Alcohol-Initiated Dediazoniation of Aryldiazonium Ions to Aryl Radicals: A Simple and Efficient Route to Arylboronates
  作者：Xiulian Zhang、Zhicheng Zhang、Yongbin Xie、Yujie Jiang、Ruibo Xu、Yuhui Luo、Chuanzhou Tao

  DOI：10.3184/174751918x15362432558247

  日期：2018.9

  A simple and efficient access to arylboronates was achieved with methanol-initiated borylation of aryldiazonium salts. Reduction of aryldiazonium ions by single electron transfer from methanol affords aryl radical species, which undergo a subsequent C–B bond formation with bis(pinacolato)diboron. This highly practical borylation process, which can be carried out on the gram-scale, enjoys operational

  通过甲醇引发的芳基重氮盐的硼酸化反应，可以简单有效地获得芳基硼酸酯。通过甲醇的单电子转移还原芳基重氮离子得到芳基自由基物种，其随后与双（频哪醇）二硼形成 C-B 键。这种高度实用的硼酸化工艺可以在克级规模上进行，操作简单，条件温和且无催化剂。
• A New Enabling Technology for Convenient Laboratory Scale Continuous Flow Processing at Low Temperatures
  作者：Duncan L. Browne、Marcus Baumann、Bashir H. Harji、Ian R. Baxendale、Steven V. Ley

  DOI：10.1021/ol2010006

  日期：2011.7.1

  conducting continuous flow processes at low temperatures on a laboratory scale is reported. The use of this cryogenic flow reactor has been demonstrated by the preparation of a variety of (hetero)aromatic boronic acids and esters via lithium halogen exchange chemistry. Furthermore, scale-up of the reaction conditions not only demonstrates the application of this device for the preparation of useful building

  报道了一种用于在实验室规模的低温下进行连续流动过程的新机器。通过经由卤化锂交换化学制备多种（杂）芳族硼酸和酯已经证明了该低温流动反应器的使用。此外，反应条件的扩大不仅证明了该装置在制备有用的结构单元中的应用，而且还结合了直接通过连接到装置上的泵头处理正丁基锂的能力。
• Investigation of a Lithium-Halogen Exchange Flow Process for the Preparation of Boronates by Using a Cryo-Flow Reactor
  作者：James A. Newby、Lena Huck、D. Wayne Blaylock、Paul M. Witt、Steven V. Ley、Duncan L. Browne

  DOI：10.1002/chem.201303736

  日期：2014.1.3

  Conducting low‐temperature organometallic reactions under continuous flow conditions offers the potential to more accurately control exotherms and thus provide more reproducible and scalable processes. Herein, progress towards this goal with regards to the lithium–halogen exchange/borylation reaction is reported. In addition to improving the scope of substrates available on a research scale, methods

  在连续流动条件下进行低温有机金属反应提供了更精确地控制放热的潜力，从而提供了更具可重复性和可扩展性的过程。在此，据报道，朝着锂-卤素交换/硼氢化反应的目标迈进了一步。除了在研究规模上改善可用底物的范围外，还描述了改善反应曲线和加快产物纯化的方法。在转向连续系统时，热电偶测量已用于跟踪放热并为有机金属试剂的连续处理提供一定的安全性。还报告了使用在线连续液-液分离设备来规避劳动密集型下游离线处理。
• Transition Metal-Free Synthesis of Pinacol Arylboronate: Regioselective Boronation of 1,3-Disubstituted Benzenes
  作者：Yan Wang、Le Wang、Ling-Yan Chen、Pinaki S. Bhadury、Zhihua Sun

  DOI：10.1071/ch13642

  日期：——

  The regioselective synthesis of pinacol arylboronate has been achieved from 1,3-disubstituted benzene through directed ortho-metallation (DoM)–borylation sequence. A wide range of substituents and borylating reagents were investigated. In situ lithiation and subsequent boronation predominantly occurred at the ortho-position to afford the desired products in moderate yields.

  通过定向正交金属化（DoM）-硼酸化顺序，从 1,3 二甲基苯实现了芳基硼酸频哪醇酯的区域选择性合成。研究了多种取代基和硼酸化试剂。原位锂化和随后的硼化主要发生在正交位置，从而以中等产率得到所需的产物。
• 화합물 및 이를 이용한 유기전기소자
  申请人：DUK SAN NEOLUX CO., LTD. 덕산네오룩스 주식회사(120150011099) Corp. No ▼ 161511-0176036BRN ▼312-86-74729

  公开号：KR20200145983A

  公开（公告）日：2020-12-31

  본 발명의 실시예들은 높은 발광효율, 낮은 구동전압, 고내열성, 색순도, 또는 수명을 향상시킬 수 있는 유기전기소자용 화합물 및 이를 이용한 유기전기소자에 관한 것이다.

  本发明的实施例涉及有机电子元件用化合物，以及利用这些化合物可以提高发光效率、降低驱动电压、提高耐热性、色纯度或延长寿命的有机电子元件。