(4-氯-2-氰基苯基)硼酸 | 819070-53-6

• 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: (4-氯-2-氰基苯基)硼酸
• 英文名称: (4-chloro-2-cyanophenyl)boronic acid
• 英文别名: 4-Chloro-2-cyanophenylboronic acid
• CAS: 819070-53-6
• 化学式: C₇H₅BClNO₂
• mdl: MFCD10696656
• 分子量: 181.386
• InChiKey: SWBTXCSSSBWRQF-UHFFFAOYSA-N

物化性质

• 熔点：
  >285 °C (decomp)
• 沸点：
  374.7±52.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.2
• 氢给体数：
  2
• 氢受体数：
  3

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 4-Chloro-2-cyanophenylboronic 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-Chloro-2-cyanophenylboronic acid
CAS number: 819070-53-6

---

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, 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
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C7H5BClNO2
Molecular weight: 181.4

---

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, hydrogen chloride.

---

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-氯-2-氰基苯基)硼酸 在 四(三苯基膦)钯 氢气 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 tert-butyl 4-(4-chloro-2-cyanophenyl)piperidine-1-carboxylate
  参考文献：
  名称：

  有效合成高度官能化的4-芳基哌啶

  摘要：

  在该手稿中，公开了功能化的4-芳基哌啶的有效合成。讨论了形成关键的芳基-哌啶sp3碳-碳键的几种合成方法，包括通过酰基吡啶鎓离子与芳基格氏试剂反应形成相应的二氢吡啶而形成哌啶的可扩展路线。描述了通过二氢吡啶中间体获得BOC保护的哌啶的方法。

  DOI：

  10.1016/j.tet.2004.09.092
• 作为产物：
  描述：

  3-氯苯腈 在 正丁基锂 、 1,3-二溴-5,5-二甲基海因 、 硼酸三异丙酯 、 硫酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.33h， 生成 (4-氯-2-氰基苯基)硼酸
  参考文献：
  名称：

  有效合成高度官能化的4-芳基哌啶

  摘要：

  在该手稿中，公开了功能化的4-芳基哌啶的有效合成。讨论了形成关键的芳基-哌啶sp3碳-碳键的几种合成方法，包括通过酰基吡啶鎓离子与芳基格氏试剂反应形成相应的二氢吡啶而形成哌啶的可扩展路线。描述了通过二氢吡啶中间体获得BOC保护的哌啶的方法。

  DOI：

  10.1016/j.tet.2004.09.092

文献信息

• [EN] BRIDGED BICYCLIC KALLIKREIN INHIBITORS<br/>[FR] INHIBITEURS BICYCLIQUES PONTÉS DE LA KALLIKRÉINE
  申请人：GLOBAL BLOOD THERAPEUTICS INC

  公开号：WO2016201052A1

  公开（公告）日：2016-12-15

  Provided herein are kallikrein modulating compounds, pharmaceutical compositions comprising the same, and uses thereof.

  本文提供了调节激肽酶的化合物、包含这些化合物的药物组合物，以及它们的用途。
• Palladium-Catalyzed Cascade Reaction of <i>o</i>-Cyanobiaryls with Arylboronic Acids: Synthesis of 5-Arylidene-7-aryl-5<i>H</i>-dibenzo[<i>c</i>,<i>e</i>]azepines
  作者：Xinrong Yao、Yinlin Shao、Maolin Hu、Yuanzhi Xia、Tianxing Cheng、Jiuxi Chen

  DOI：10.1021/acs.orglett.9b02351

  日期：2019.10.4

  A palladium-catalyzed cascade reaction of 2'-acetyl-[1,1'-biphenyl]-2-carbonitriles with arylboronic acids is developed. This reaction affords a new class of seven-membered 5-arylidene-7-aryl-5H-dibenzo[c,e]azepines with good functional group compatibility and selectivity. Reaction mechanistic study suggests that this transformation involves carbopalladation of nitrile and subsequent intramolecular

  开发了钯催化的2'-乙酰基-[1,1'-联苯] -2-腈与芳基硼酸的级联反应。该反应提供了具有良好的官能团相容性和选择性的新型的七元5-亚芳基-7-芳基-5H-二苯并[c，e]氮杂。反应机理研究表明，这种转变涉及腈的碳巴巴定化和随后的分子内环化，然后是氧化性Heck偶联。
• Study of photophysical properties in bronsted acids for nitrogen atoms with different hybrid (sp, sp2, sp3) orbitals
  作者：Zhou Wang、Kaibo Hu、Chichong Lu、Guofan Jin

  DOI：10.1007/s13738-024-03048-0

  日期：2024.7

  Fluorescent tiny molecules that are resistant to acid have long been the center of interest. The nitrogen atoms on benzyl cyanide were sp hybridized, while the two nitrogen atoms at pyrimidine were sp2 hybridized in the primary structure that we constructed. With the addition of a protonic acid (H2SO4, CH3SO3H, and HF), the nitrogen atoms at acridine underwent sp3 hybridization, which caused the hydrogen

  耐酸的荧光微小分子长期以来一直是人们关注的焦点。在我们构建的一级结构中，苯乙腈上的氮原子是sp杂化的，而嘧啶上的两个氮原子是sp 2 杂化的。添加质子酸（H 2 SO 4 、CH 3 SO 3 H 和 HF）后，氮原子吖啶发生sp 3 杂化，导致氢质子与三种类型的氮原子发生不同程度的相互作用。电子云密度的这种分布导致荧光发射减少。此外，利用Gaussian 09软件和DFT计算对其轨道构象进行建模，即最高占据分子轨道-最低未占据分子轨道（HOMO-LUMO）。此外，其晶体结构属于非均匀性较强的斜方晶系（a = 8.9160 (4) Å, b = 44.289 (3) Å, c = 9.6131 (7) Å, α = 90°, β = 90° , γ = 90°, V = 3796.0 (4) Å 3 , z = 4, Dc = 1.244 g/cm 3 )。  图形概要
• Potent GCN2 Inhibitor Capable of Reversing MDSC-Driven T Cell Suppression Demonstrates In Vivo Efficacy as a Single Agent and in Combination with Anti-Angiogenesis Therapy
  作者：Jeffrey J. Jackson、Grant M. Shibuya、Buvana Ravishankar、Lavanya Adusumilli、Delia Bradford、Dirk G. Brockstedt、Cyril Bucher、Minna Bui、Cynthia Cho、Christoph Colas、Gene Cutler、Adrian Dukes、Xinping Han、Dennis X. Hu、Scott Jacobson、Paul D. Kassner、George E. Katibah、Michelle Yoo Min Ko、Urvi Kolhatkar、Paul R. Leger、Anqi Ma、Lisa Marshall、Jack Maung、Andrew A. Ng、Akinori Okano、Deepa Pookot、Daniel Poon、Chandru Ramana、Maureen K. Reilly、Omar Robles、Jacob B. Schwarz、Anton A. Shakhmin、Hunter P. Shunatona、Raashi Sreenivasan、Parcharee Tivitmahaisoon、Mengshu Xu、Thant Zaw、David J. Wustrow、Mikhail Zibinsky

  DOI：10.1021/acs.jmedchem.2c00736

  日期：2022.10.13