2-(3-乙炔基苯基)-硼酸频哪醇酯 | 946168-04-3

• 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-(3-乙炔基苯基)-硼酸频哪醇酯
• 中文别名: 2-(3-乙炔-苯基)-4,4,5,5-四甲基-[1,3,2]二噁硼烷；3-乙炔基苯硼酸频哪醇酯
• 英文名称: 2-(3-ethynylphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
• 英文别名: 2-(3-Ethynylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 946168-04-3
• 化学式: C₁₄H₁₇BO₂
• mdl: MFCD16294529
• 分子量: 228.099
• InChiKey: SJDFLZSEQGKSDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  330.0±25.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险类别码：
  R22
• 海关编码：
  2934999090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
2-(3-Ethynylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Product Name:
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

---

Section 3. Composition/information on ingredients.
2-(3-Ethynylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Ingredient name:
CAS number: 946168-04-3

---

Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

---

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.

---

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.

---

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:

---

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.

---

Section 9. Physical and chemical properties
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C14H17BO2
Molecular weight: 228.1

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-(3-乙炔基苯基)-硼酸频哪醇酯 在 tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate 、 copper(l) chloride 作用下， 以 吡啶 、 1,2-二氯乙烷 为溶剂， 反应 12.5h， 生成 2',5'-bis[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]spiro[9-silafluorene-9,1'-silole]
  参考文献：
  名称：

  Ruthenium-catalysed double trans-hydrosilylation of 1,4-diarylbuta-1,3-diynes leading to 2,5-diarylsiloles

  摘要：

  二氢硅烷在阳离子钌催化剂的存在下与1,4-二芳基丁-1,3-二炔发生双转式氢硅化反应，生成2,5-二芳基硅烯；尤其是，9-硅氟烯是一个良好的氢硅化试剂，可以高产率地生成螺旋型硅烯。

  DOI：

  10.1039/b703397d
• 作为产物：
  描述：

  (1-重氮基-2-氧代丙基)膦酸二甲酯 、 3-(4,4,5,5-四甲基-1,3,2-二氧硼烷)苯甲醛 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 2-(3-乙炔基苯基)-硼酸频哪醇酯
  参考文献：
  名称：

  顺序 Seyferth-Gilbert/CuAAC 反应：应用于从醛中一锅法合成三唑

  摘要：

  报道了一种可靠且操作简单的一锅反应，用于各种醛的单碳同系化，然后是铜催化的叠氮化物-炔烃 1,3-偶极环加成 (CuAAC)。1,4-二取代的 1,2,3-三唑可以从各种容易获得的醛中以良好到极好的收率获得，而无需分离炔中间体。该反应具有广泛的范围，允许形成新的生物共轭物，并用于合成新的基于硼酸的荧光传感器。

  DOI：

  10.1055/s-2007-990877

文献信息

• [EN] SUBSTITUTED QUINOXALINE DERIVATIVES<br/>[FR] DÉRIVÉS DE QUINOXALINE SUBSTITUÉS
  申请人：SELVITA S A

  公开号：WO2016180537A1

  公开（公告）日：2016-11-17

  The present invention relates to substituted quinoxaline derivatives. These compounds are useful for the prevention and/or treatment of several medical conditions including hyperproliferative disorders and diseases.

  这项发明涉及取代喹喔啉衍生物。这些化合物对预防和/或治疗包括过度增殖性疾病在内的多种医疗状况具有用处。
• Specific cross-dimerization of terminal alkynes via Pd/TMEDA catalysis
  作者：Lixin Liu、Jianyu Dong、Zuqi Fu、Lebin Su、Shaofeng Wu、Qian Shang、Shuang-Feng Yin、Yongbo Zhou

  DOI：10.1007/s11426-022-1388-5

  日期：2022.12

  The cross-dimerization of terminal alkynes is the most straightforward and attractive approach to differently substituted 1,3-enynes, which are vital structural motifs in natural products, biologically active compounds, and organic functional materials, etc. However, due to the inherent issues of the stereo-, regio-, and chemoselectivity, the strategy is less explored and remains problematic in substrate

  末端炔烃的交叉二聚化是不同取代的 1,3-烯炔的最直接和有吸引力的方法，这是天然产物、生物活性化合物和有机功能材料等中的重要结构基序。然而，由于固有的问题在立体选择性、区域选择性和化学选择性方面，该策略的探索较少，在底物范围、选择性和催化体系筛选等方面仍存在问题。本文在 Pd/TMEDA 催化下开发了末端炔烃的特异性交叉二聚化，从而产生一系列宝石-1,3-烯炔（58 个例子），完全中等至高产率，具有出色的官能团耐受性。环钯化合物可能是关键的中间体，它可以进行抗加成 - 碳金属化，并导致排他性的交叉选择性。该反应前所未有的特点，如抗加成碳金属化、易于控制选择性、广泛的供体炔烃和非常简单的催化条件，使其不仅可以轻松合成功能多样的 1,3-烯炔烃，而且对于教科书的反应也有了长足的进步。
• Incorporating Synthetic Accessibility in Drug Design: Predicting Reaction Yields of Suzuki Cross-Couplings by Leveraging AbbVie’s 15-Year Parallel Library Data Set
  作者：Priyanka Raghavan、Alexander J. Rago、Pritha Verma、Majdi M. Hassan、Gashaw M. Goshu、Amanda W. Dombrowski、Abhishek Pandey、Connor W. Coley、Ying Wang

  DOI：10.1021/jacs.4c00098

  日期：2024.6.5

  we demonstrate the application of this approach to suggest structurally and electronically similar building blocks to replace those predicted or observed to be unsuccessful prior to or after synthesis, respectively. The yield prediction model was used to select similar monomers predicted to have higher yields, resulting in greater synthesis efficiency of relevant drug-like molecules.

  尽管越来越多地使用计算工具来补充药物化学家在药物设计方面的专业知识和直觉，但预测药物化学工作中的合成产量仍然是一个尚未解决的挑战。现有的设计工作流程可以从反应产率预测中受益匪浅，因为可以减少贵重材料的浪费，并且可以提供更多数量的相关化合物来推进设计、制造、测试、分析 (DMTA) 周期。在这项工作中，我们详细介绍了艾伯维药物化学库数据集的评估，以构建机器学习模型来预测铃木偶联反应的产率。密度泛函理论 (DFT) 衍生的特征和摩根指纹的结合被认为比单热编码基线模型表现更好，提供了令人鼓舞的结果。总体而言，我们观察到 15 年回顾性图书馆数据集中对未见过的反应物结构的适度概括。此外，我们将模型做出的预测与药物化学家做出的预测进行比较，发现该模型通常可以更准确地预测反应成功和反应产率。最后，我们演示了这种方法的应用，以建议结构和电子上相似的构建块，以分别替换那些在合成之前或之后预测或观察到不成功