2-溴乙基基苯硼酸频哪醇酯 | 377780-72-8

• 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 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-溴乙基基苯硼酸频哪醇酯
• 中文别名: 2-溴甲基苯基硼酸频哪醇酯；2-(2-(溴甲基)苯基)-4,4,5,5-四甲基-1,3,2-二氧杂硼烷；2-(溴甲基)苯硼酸频哪酯；2-溴甲基苯硼酸频那醇酯；2-溴甲基苯硼酸频哪醇酯
• 英文名称: 2-bromomethylphenylboronic acid pinacol ester
• 英文别名: 2-(2-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；2-[2-(bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 377780-72-8
• 化学式: C₁₃H₁₈BBrO₂
• 分子量: 297.0
• InChiKey: ROIXSNLOYHDYBP-UHFFFAOYSA-N

物化性质

• 熔点：
  78-80°C
• 沸点：
  360.6±25.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• TSCA：
  No
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• 安全说明：
  S26,S36/37/39
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 包装等级：
  II
• 危险类别：
  8
• 危险品运输编号：
  3261
• 储存条件：
  请保持冷饮

SDS

Material Safety Data Sheet

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

---

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
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

---

Section 3. Composition/information on ingredients.
Ingredient name: 2-Bromomethylphenylboronic acid, pinacol ester
CAS number: 377780-72-8

---

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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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.

---

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.
Storage: Store in closed vessels, refrigerated.

---

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
Appearance: Not specified
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C13H18BBrO2
Molecular weight: 297.0

---

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.

---

Section 11. Toxicological information
No data.

---

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.

---

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-溴乙基基苯硼酸频哪醇酯 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(2-(叠氮甲基)苯基)-4,4,5,5-四甲基-1,3,2-二氧杂硼烷
  参考文献：
  名称：

  通过光氧化还原电子转移策略实现高区域选择性叠氮化物-炔烃环加成的可见光介导的点击化学。

  摘要：

  Click化学专注于使用简单的前体进行分子的精细合成的高选择性反应的开发。毋庸置疑，CuI催化的叠氮化物-炔烃环加成（CuAAC）是点击化学最有价值的例子之一，但由于需要额外的还原剂和配体以及细胞毒性铜，因此受到一些限制。在这里，我们展示了一种新颖的叠氮化物-炔烃环加成反应的策略，该策略涉及光氧化还原电子转移自由基机理，而不是传统的金属催化配位过程。这种新开发的光催化的叠氮化物-炔烃环加成反应可以在室温下，在空气和可见光存在的条件下，在温和条件下进行，显示出良好的官能团耐受性，优异的原子经济性，高达99％的高收率，和绝对的区域选择性，提供了各种1,4-二取代的1,2,3-三唑衍生物，包括生物活性分子和药物。使用可回收的光催化剂，太阳能和水作为溶剂，使该光催化系统具有可持续性和环境友好性。此外，叠氮化物-炔烃环加成反应可以在具有优异区域选择性的无金属催化剂的存在下进行光催化，这代表了点击化学

  DOI：

  10.1002/chem.202000252
• 作为产物：
  描述：

  trimethyl-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-methylbenzyl]-quaternaryammonium bromide 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 aq. phosphate buffer 、 重水 、 甲苯 、 乙腈 为溶剂， 反应 4.0h， 生成 2-溴乙基基苯硼酸频哪醇酯
  参考文献：
  名称：

  取代基对芳基硼酸酯前体的氧化甲基醌氧化生成的影响

  摘要：

  一系列含有不同芳族取代基和各种苄基离去基团（BR或N-芳基硼酸酯的+我3溴- ）已被合成。已经研究了取代基对其与H 2 O 2的反应性和甲基化醌（QM）形成的影响。NMR光谱和乙基乙烯基醚（EVE）捕获实验分别用于确定反应机理和QM形成。在硼酸酯的氧化裂解过程中不会产生QM，而是在生理条件下通过苯酚产物的后续转化产生的。吸电子取代基（例如芳族F，NO 2或苄基N ）促进了氧化脱硼+我3溴- ，而给电子取代基或更好的离去基团有利于QM产生。包含芳香族CH 3或OMe基团或良好离去基团（Br）的化合物可在生理条件下有效产生QM。最后，通过使用哈米特图建立了芳基硼酸酯的结构与活性之间的定量关系。现在可以预测地调整芳基硼酸/酯的反应性以及抑制或促进QM的形成。此调整很重要，因为某些应用程序可能会受益，而其他应用程序可能会受到QM生成的限制。

  DOI：

  10.1002/chem.201300539

文献信息

• X-ray Structures, Photophysical Characterization, and Computational Analysis of Geometrically Constrained Copper(I)−Phenanthroline Complexes
  作者：John Cody、Jeanette Dennisson、Joshua Gilmore、Donald G. VanDerveer、Maged M. Henary、Alan Gabrielli、C. David Sherrill、Yiyun Zhang、Chia-Pin Pan、Clemens Burda、Christoph J. Fahrni

  DOI：10.1021/ic034529j

  日期：2003.8.1

  originate predominantly from the copper d(xz) orbital. The computational analysis identifies an excited-state manifold with a number of close-lying, potentially emissive triplet states and is in agreement with the multiexponential decay kinetics of the MLCT luminescence. The relationship between structural and photophysical data of the studied Cu(I) mono-phenanthroline complexes agrees well with current models

  通过X射线结构分析表征了一系列三个几何受约束的C（2）-对称的Cu（I）单菲咯啉配合物，并通过吸收和发射光谱研究了它们的光物理性质。可见光激发产生了金属至配体的电荷转移（MLCT）激发态，其发光寿命高达155 ns。超快速瞬态吸收光谱技术提供了对激发态动力学的进一步了解，并暗示了对于所有三种配合物，菲咯啉自由基阴离子的形成。与电化学测量结果一致，数据进一步表明，配位重排涉及激发态的非辐射失活。根据随时间变化的密度泛函理论计算（B3LYP / 6-31G），主要的MLCT过渡沿复合物的C（2）轴极化，并且主要起源于铜d（xz）轨道。计算分析确定了一个激发态流形，该激发态流形具有许多紧密的，可能发射的三重态，并且与MLCT发光的多指数衰减动力学一致。研究的Cu（I）单菲咯啉配合物的结构和光物理数据之间的关系与描述相关的Cu（I）双二亚胺配合物的光物理的当前模型非常吻合。潜在的发射三重态，并且与
• The Discovery of a Palladium(II)-Initiated Borono-Catellani Reaction
  作者：Shuqing Chen、Ze-Shui Liu、Tao Yang、Yu Hua、Zhiyu Zhou、Hong-Gang Cheng、Qianghui Zhou

  DOI：10.1002/anie.201803865

  日期：2018.6.11

  Reported is a novel palladium(II)‐initiated Catellani‐type reaction that utilizes widely accessible aryl boronic acids as the substrates instead of aryl halides, thereby greatly expanding the existing scope of this powerful transformation. This borono‐Catellani reaction was promoted by cooperative catalysis between Pd(OAc)2 and the inexpensive 5‐norbornene‐2‐carbonitrile. Practicality is the striking

  据报道，是一种新颖的钯（II）引发的卡塞拉尼型反应，该反应利用可广泛使用的芳基硼酸而不是卤代芳基作为底物，从而大大扩展了这种有力转化的现有范围。Pd（OAc）2之间的协同催化促进了这种硼诺-卡泰拉尼反应以及价格低廉的5-降冰片烯2-腈。实用性是该反应的显着特征：它在环境温度下对空气开放，不需要膦配体。这种温和，化学选择性和可扩展的方案与各种现成的官能化芳基硼酸和溴化物以及终止烯烃（50例，收率39–97％）兼容。此外，还证实了卡诺拉尼和经典卡特兰尼反应之间的正交反应性。预期这项工作将为开发新颖的卡泰拉尼型反应开辟新途径。
• Preparation of labeled aromatic amino acids <i>via</i> late-stage ¹⁸F-fluorination of chiral nickel and copper complexes
  作者：Austin Craig、Niklas Kolks、Elizaveta A. Urusova、Johannes Zischler、Melanie Brugger、Heike Endepols、Bernd Neumaier、Boris D. Zlatopolskiy

  DOI：10.1039/d0cc02223c

  日期：——

  A general protocol for the preparation of 18F-labeled AAAs and α-methyl-AAAs applying alcohol-enhanced Cu-mediated radiofluorination of Bpin-substituted chiral complexes using Ni/Cu-BPX templates as double protecting groups is reported. The chiral auxiliaries are easily accessible from commercially available starting materials in a few synthetic steps. The versatility of the method was demonstrated

  报导了使用Ni / Cu-BPX模板作为双重保护基团，应用醇增强的Cu介导的Bpin取代的手性配合物的放射性氟化，制备18个F标记的AAA和α-甲基AAA的通用方案。通过一些合成步骤，可以容易地从市售起始原料获得手性助剂。该方法的多功能性通过一系列[ 18 F] F-AAA的高产制备以及将该协议成功实施到自动化放射合成模块中得到了证明。
• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：CTXT PTY LTD

  公开号：WO2020002587A1

  公开（公告）日：2020-01-02

  A compound of formula (I), or a pharmaceutically acceptable salt thereof.

  式（I）的化合物，或其药用可接受的盐。
• [EN] NOVEL SOLUBLE GUANYLATE CYCLASE ACTIVATORS AND THEIR USE<br/>[FR] NOUVEAUX ACTIVATEURS DE GUANYLATE CYCLASE SOLUBLE ET LEUR UTILISATION
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2015033307A1

  公开（公告）日：2015-03-12

  The invention relates to activators of soluble guanylate cyclase of formula (I) and their use in pharmaceutical compositions, primarily topically administered ophthalmic compositions. The pharmaceutical compositions are useful for reducing intraocular pressure in animals of the mammalian species.

  该发明涉及公式（I）的可溶性鸟苷酸环化酶激活剂及其在制药组合物中的应用，主要是局部给药的眼科组合物。这些制药组合物对于降低哺乳动物种类的动物的眼压是有用的。