2-醛基噻吩-4-硼酸频哪醇酯 | 881381-12-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-醛基噻吩-4-硼酸频哪醇酯
• 中文别名: 2-甲酰基噻吩-4-硼酸频那醇酯；2-甲酰噻吩-4-硼酸频哪醇酯
• 英文名称: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)thiophene-2-carbaldehyde
• 英文别名: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarbaldehyde；4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde
• CAS: 881381-12-0
• 化学式: C₁₁H₁₅BO₃S
• 分子量: 238.115
• InChiKey: TWTLMECTLHOTSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

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：
  H315,H319,H335
• 储存条件：
  存储条件：2-8°C，避光，并保存在惰性气体中。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 2-Formylthiophene-4-boronic acid, pinacol ester
Synonyms: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 2-Formylthiophene-4-boronic acid, pinacol ester
CAS number: 881381-12-0

---

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: C11H15BO3S
Molecular weight: 238.1

---

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

  2-醛基噻吩-4-硼酸频哪醇酯 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 5,5'-dialdehyde-3,3'-bidithiophene
  参考文献：
  名称：

  高荧光发射5、5'-二苯乙烯基-3、3'-联噻吩：合成，晶体结构，光电和热学性质

  摘要：

  七5,5'-二苯乙烯基-3,3'-联噻吩衍生物（1 - 7）与A-π-A或d-π-d结构的合成和它们的光物理，电化学和热性能进行了研究。光致发光实验表明该化合物具有高荧光发射。在光物理研究中，具有硝基取代基的化合物2显示出显着的溶剂变色，热变色和聚集诱导发射（AIE）特性。循环伏安法和热重分析表明2具有良好的电子亲和力和热稳定性。通过单晶X射线衍射鉴定分子结构和堆积排列。电子跃迁的理论计算解释了观察到的2孔特殊光学行为。的优良的光学特性2使其成为光电有希望的发射极。

  DOI：

  10.1016/j.dyepig.2020.108396
• 作为产物：
  描述：

  4-溴-2-噻吩甲醛 、 联硼酸频那醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-醛基噻吩-4-硼酸频哪醇酯
  参考文献：
  名称：

  高荧光发射5、5'-二苯乙烯基-3、3'-联噻吩：合成，晶体结构，光电和热学性质

  摘要：

  七5,5'-二苯乙烯基-3,3'-联噻吩衍生物（1 - 7）与A-π-A或d-π-d结构的合成和它们的光物理，电化学和热性能进行了研究。光致发光实验表明该化合物具有高荧光发射。在光物理研究中，具有硝基取代基的化合物2显示出显着的溶剂变色，热变色和聚集诱导发射（AIE）特性。循环伏安法和热重分析表明2具有良好的电子亲和力和热稳定性。通过单晶X射线衍射鉴定分子结构和堆积排列。电子跃迁的理论计算解释了观察到的2孔特殊光学行为。的优良的光学特性2使其成为光电有希望的发射极。

  DOI：

  10.1016/j.dyepig.2020.108396

文献信息

• CHEMICAL COMPOUNDS
  申请人：Deng Jianghe

  公开号：US20090143372A1

  公开（公告）日：2009-06-04

  The invention is directed to novel indole carboxamide derivatives. Specifically, the invention is directed to compounds according to formula I: where R1, R2, R3, U and V are defined below and to pharmaceutically acceptable salts thereof. The compounds of the invention are inhibitors of IKK2 and can be useful in the treatment of disorders associated with inappropriate IKK2 (also known as IKKβ) activity, such as rheumatoid arthritis, asthma, and COPD (chronic obstructive pulmonary disease). Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting IKK2 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  这项发明涉及新型吲哚羧酰胺衍生物。具体而言，该发明涉及符合以下式I的化合物： 其中R1、R2、R3、U和V如下定义，并且其药学上可接受的盐。该发明的化合物是IKK2的抑制剂，可用于治疗与不当IKK2（也称为IKKβ）活性相关的疾病，如类风湿性关节炎、哮喘和慢性阻塞性肺病（COPD）。因此，该发明进一步涉及包含该发明化合物的药物组合物。该发明还进一步涉及使用该发明化合物或包含该发明化合物的药物组合物抑制IKK2活性和治疗相关疾病的方法。
• HandaPhos: A General Ligand Enabling Sustainable ppm Levels of Palladium-Catalyzed Cross-Couplings in Water at Room Temperature
  作者：Sachin Handa、Martin P. Andersson、Fabrice Gallou、John Reilly、Bruce H. Lipshutz

  DOI：10.1002/anie.201510570

  日期：2016.4.11

  complexed in a 1:1 ratio with Pd(OAc)2, enables Pd‐catalyzed cross‐couplings to be run using ≤1000 ppm of this pre‐catalyst. Applications to Suzuki–Miyaura reactions involving highly funtionalized reaction partners are demonstrated, all run using environmentally benign nanoreactors in water at ambient temperatures. Comparisons with existing state‐of‐the‐art ligands and catalysts are discussed herein.

  新的单膦配体HandaPhos已被鉴定为，当与Pd（OAc）2以1：1的比例络合时，可使用≤1000ppm的这种预催化剂进行Pd催化的交叉偶联。展示了在涉及高度官能化反应伙伴的Suzuki–Miyaura反应中的应用，所有反应均使用环境友好的纳米反应器在环境温度下的水中进行。本文讨论了与现有最​​先进的配体和催化剂的比较。
• Rh^III-Catalyzed Direct Heteroarylation of C(sp³)–H and C(sp²)–H Bonds in Heterocycles with <i>N</i>-Heteroaromatic Boronates
  作者：Huai-Wei Wang、Jia-Xue Wu、Yu-Han Qiao、Yong-Fei Li、Da-Cheng Li、Jian-Min Dou、Qing-Xia Yao、Yi Lu

  DOI：10.1021/acs.orglett.1c02546

  日期：2021.9.17

  Herein, we disclose a RhIII-catalyzed heteroarylation of C(sp3)–H and C(sp2)–H bonds in heterocycles with organoboron reagents. This protocol displays high efficiency and excellent functional group tolerance. A range of heterocyclic boronates with strong coordinating atoms, including pyridine, pyrimidine, pyrazole, thiophene, and furan derivatives, can be extensively served as the coupling reagents

  在此，我们公开了用有机硼试剂使杂环中的 C(sp 3 )-H 和 C(sp 2 )-H 键发生 Rh III催化的杂芳基化反应。该协议显示出高效率和出色的官能团耐受性。一系列具有强配位原子的杂环硼酸酯，包括吡啶、嘧啶、吡唑、噻吩和呋喃衍生物，可广泛用作偶联剂。直接杂芳基化方法可以在合成具有多个杂环的药物分子方面提供潜在的应用。
• Chemical Compounds
  申请人：Kerns K. Jeffrey

  公开号：US20070254873A1

  公开（公告）日：2007-11-01

  The invention is directed to novel indole carboxamide derivatives. Specifically, the invention is directed to compounds according to formula I: where R1, R2, R3, U and V are defined below and to pharmaceutically acceptable salts thereof. The compounds of the invention are inhibitors of IKK2 and can be useful in the treatment of disorders associated with inappropriate IKK2 (also known as IKKβ) activity, such as rheumatoid arthritis, asthma, and COPD (chronic obstructive pulmonary disease). Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting IKK2 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  本发明涉及新型吲哚羧酰胺衍生物。具体而言，本发明涉及公式I所示的化合物：其中R1，R2，R3，U和V如下所定义，及其药学上可接受的盐。本发明的化合物是IKK2的抑制剂，可用于治疗与不适当的IKK2（也称为IKKβ）活性有关的疾病，如类风湿性关节炎、哮喘和COPD（慢性阻塞性肺疾病）。因此，本发明还涉及包含本发明化合物的药物组合物。本发明还进一步涉及使用本发明化合物或包含本发明化合物的药物组合物来抑制IKK2活性和治疗与此相关的疾病的方法。
• Chemical compounds
  申请人：Glaxo Group Limited

  公开号：US07858796B2

  公开（公告）日：2010-12-28

  The invention is directed to novel indole carboxamide derivatives. Specifically, the invention is directed to compounds according to formula I: where R1, R2, R3, U and V are defined below and to pharmaceutically acceptable salts thereof. The compounds of the invention are inhibitors of IKK2 and can be useful in the treatment of disorders associated with inappropriate IKK2 (also known as IKKβ) activity, such as rheumatoid arthritis, asthma, and COPD (chronic obstructive pulmonary disease). Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting IKK2 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  本发明涉及新型吲哚羧酰胺衍生物。具体而言，本发明涉及公式I所示的化合物，其中R1、R2、R3、U和V的定义如下，以及其药学上可接受的盐。本发明的化合物是IKK2的抑制剂，可用于治疗与不适当IKK2（也称为IKKβ）活性相关的疾病，如类风湿性关节炎、哮喘和COPD（慢性阻塞性肺疾病）。因此，本发明还涉及包含该化合物的制药组合物。本发明还进一步涉及使用该化合物或包含该化合物的制药组合物来抑制IKK2活性和治疗与之相关的疾病的方法。