[4-(哌嗪-1-基)苯基]硼酸 | 513246-99-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: [4-(哌嗪-1-基)苯基]硼酸
• 英文名称: 4-piperazin-1-ylphenylboronic acid
• 英文别名: 1-(4-chlorophenyl)piperazine；4-piperazine phenylboronic acid；[4-(Piperazin-1-yl)phenyl]boronic acid；(4-piperazin-1-ylphenyl)boronic acid
• CAS: 513246-99-6
• 化学式: C₁₀H₁₅BN₂O₂
• 分子量: 206.052
• InChiKey: WEKCEGUGFNLQIA-UHFFFAOYSA-N

物化性质

• 沸点：
  437.2±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.22
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.7
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2933599090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 4-(Piperazin-1-yl)phenylboronic acid
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 4-(Piperazin-1-yl)phenylboronic acid
CAS number: 513246-99-6

---

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.

---

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, refrigerated.
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
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C10H15BN2O2
Molecular weight: 206.0

---

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.

---

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：

  [4-(哌嗪-1-基)苯基]硼酸 在 potassium hydrogen difluoride 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 0.5h， 以0.42 g的产率得到potassium trifluoro(4-(piperazin-1-yl)phenyl)borate
  参考文献：
  名称：

  镍催化四羟基二硼 [B2(OH)4] 卤化物和拟卤化物的硼化反应

  摘要：

  芳基硼酸作为试剂和目标结构在各种有用的应用中变得越来越重要。最近，报道了使用原子经济的四羟基二硼（BBA）试剂在钯催化下合成芳基硼酸。钯的高成本，加上钯和铜催化工艺的一些限制，促使我们开发一种替代方法。因此，已经制定了使用四羟基二硼（BBA）对芳基和杂芳基卤化物和拟卤化物进行镍催化的硼基化反应。该反应被证明具有广泛的官能团耐受性并适用于许多杂环体系。据我们所知，这里提供的例子代表了在室温下进行的唯一有效的镍催化宫浦硼化反应。

  DOI：

  10.1021/jo401104y
• 作为产物：
  描述：

  1-(4-氯苯基)哌嗪 在 四羟基二硼 、 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 [4-(哌嗪-1-基)苯基]硼酸
  参考文献：
  名称：

  镍催化四羟基二硼 [B2(OH)4] 卤化物和拟卤化物的硼化反应

  摘要：

  芳基硼酸作为试剂和目标结构在各种有用的应用中变得越来越重要。最近，报道了使用原子经济的四羟基二硼（BBA）试剂在钯催化下合成芳基硼酸。钯的高成本，加上钯和铜催化工艺的一些限制，促使我们开发一种替代方法。因此，已经制定了使用四羟基二硼（BBA）对芳基和杂芳基卤化物和拟卤化物进行镍催化的硼基化反应。该反应被证明具有广泛的官能团耐受性并适用于许多杂环体系。据我们所知，这里提供的例子代表了在室温下进行的唯一有效的镍催化宫浦硼化反应。

  DOI：

  10.1021/jo401104y

文献信息

• [EN] CATHEPSIN CYSTEINE PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE PROTEASES A CYSTEINE DE TYPE CATHEPSINE
  申请人：MERCK FROSST CANADA INC

  公开号：WO2004022526A1

  公开（公告）日：2004-03-18

  This invention relates to class of compounds which are cysteine protease inhibitors, including but not limited to, inhibitors of cathepsins K, L, S and B. These compounds are useful for treating diseases in which inhibition of bone resorption is indicated, such as osteoporosis. They have the following structure: Formula (I).

  这项发明涉及一类化合物，这些化合物是半胱氨酸蛋白酶抑制剂，包括但不限于对卡特普辛K、L、S和B的抑制剂。这些化合物可用于治疗需要抑制骨吸收的疾病，如骨质疏松症。它们具有以下结构：化学式（I）。
• Practical Asymmetric Synthesis of a Potent Cathepsin K Inhibitor. Efficient Palladium Removal Following Suzuki Coupling
  作者：Cheng-yi Chen、Philippe Dagneau、Edward J. J. Grabowski、Renata Oballa、Paul O'Shea、Peppi Prasit、Joël Robichaud、Rich Tillyer、Xin Wang

  DOI：10.1021/jo0205614

  日期：2003.4.1

  A large-scale, chromatography-free synthesis of a potent and selective Cathepsin K inhibitor 1 is reported. The key asymmetric center was installed by addition of (R)-pantolactone to the in situ-generated ketene 4a. The final step of the convergent synthesis of 1 was completed via Suzuki coupling of aryl bromide 7a with unprotected aryl piperazine boronic acid 13. Residual palladium and iron generated

  据报道，有效且选择性的组织蛋白酶K抑制剂1的大规模无色谱合成。通过将（R）-泛内酯添加到原位生成的乙烯酮4a中来安装关键的不对称中心。通过芳基溴化物7a与未保护的芳基哌嗪硼酸13的Suzuki偶联，完成1的收敛合成的最后一步。通过使用乳酸进行简单的萃取后处理，即可从粗产物1中有效地除去在Suzuki偶联中产生的残留钯和铁。
• Discovery of Small Molecule Mer Kinase Inhibitors for the Treatment of Pediatric Acute Lymphoblastic Leukemia
  作者：Jing Liu、Chao Yang、Catherine Simpson、Deborah DeRyckere、Amy Van Deusen、Michael J. Miley、Dmitri Kireev、Jacqueline Norris-Drouin、Susan Sather、Debra Hunter、Victoria K. Korboukh、Hari S. Patel、William P. Janzen、Mischa Machius、Gary L. Johnson、H. Shelton Earp、Douglas K. Graham、Stephen V. Frye、Xiaodong Wang

  DOI：10.1021/ml200239k

  日期：2012.2.9

  small molecule Mer kinase inhibitors. Several pyrazolopyrimidine derivatives effectively inhibit Mer kinase activity at subnanomolar concentrations. Furthermore, the lead compound shows a promising selectivity profile against a panel of 72 kinases and has excellent pharmacokinetic properties. We also describe the crystal structure of the complex between the lead compound and Mer, opening new opportunities

  异位 Mer 表达促进促生存信号传导，并有助于儿童急性淋巴细胞白血病 (ALL) 的白血病发生和化学抗性。因此，Mer 激酶抑制剂可能会促进白血病细胞死亡，并进一步充当化学增敏剂，提高当前 ALL 方案的疗效并降低毒性。我们已应用基于结构的设计方法来发现新型小分子 Mer 激酶抑制剂。几种吡唑并嘧啶衍生物在亚纳摩尔浓度下有效抑制 Mer 激酶活性。此外，先导化合物对一组 72 种激酶显示出有希望的选择性，并具有出色的药代动力学特性。我们还描述了先导化合物和 Mer 之间复合物的晶体结构，为进一步优化和新模板设计开辟了新的机会。
• [EN] ALPHA-CARBOLINES FOR THE TREATMENT OF CANCER<br/>[FR] ALPHA-CARBOLINES POUR LE TRAITEMENT DU CANCER
  申请人：UNIV MILANO BICOCCA

  公开号：WO2013167730A1

  公开（公告）日：2013-11-14

  The present invention relates to inhibitors of the oncogenic protein kinase ALK of formula (I) as herein described and pharmaceutical compositions thereof, as well as to key intermediates towards their synthesis. The compounds of formula (I) are useful in the preparation of a medicament, in particular for the treatment of cancer.

  本发明涉及如下式（I）所述的致癌蛋白激酶ALK的抑制剂及其药物组合物，以及用于其合成的关键中间体。式（I）的化合物在制备药物中具有用途，特别是用于癌症治疗。
• Recognition of saccharides in the NIR region with a novel fluorogenic boronolectin: in vitro and live cell labeling
  作者：Cecilia Samaniego Lopez、María Amparo Lago Huvelle、María Laura Uhrig、Federico Coluccio Leskow、Carla C. Spagnuolo

  DOI：10.1039/c4cc10425k

  日期：——

  The detection performance in solution and in live cells of a novel mono-boronic acid derivative of a near-infrared luminescent tricarbocyanine with OFF–ON response upon addition of saccharides.

  一种新型近红外荧光三氰基单硼酸衍生物，具有加入糖类后的OFF-ON响应特性，可在溶液和活细胞中进行检测。