2-甲基苯并噻唑-5-硼酸 | 590417-67-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2-甲基苯并噻唑-5-硼酸
• 英文名称: (2-methyl-1,3-benzothiazol-5-yl)boronic acid
• 英文别名: 2-methaneylbenzo[d]thiazol-5-ylboronic acid；(2-methylbenzo[d]thiazol-5-yl)boronic acid；2-methylbenzothiazole-5-boronic acid
• CAS: 590417-67-7
• 化学式: C₈H₈BNO₂S
• mdl: MFCD12025970
• 分子量: 193.034
• InChiKey: XFPZHJXTRXAWAO-UHFFFAOYSA-N

物化性质

• 沸点：
  398.8±34.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  81.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H319

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 2-Methylbenzothiazole-5-boronic acid
Synonyms: 2-Methylbenzo[d]thiazol-5-ylboronic acid

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H319: Causes serious eye irritation
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-Methylbenzothiazole-5-boronic acid
CAS number: 590417-67-7

---

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.
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
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H8BNO2S
Molecular weight: 193.0

---

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, 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-甲基苯并噻唑-5-硼酸 、 3-溴丙烯 在 dichloro(N-(diphenylphosphino)-N-isopropyl-1,1-diphenylphosphinamine) digold(I) 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以53%的产率得到5-allyl-2-methylbenzo[d]thiazole
  参考文献：
  名称：

  芳基硼酸的金催化烯丙基化：获得与金的交叉偶联反应

  摘要：

  描述了在没有牺牲氧化剂的情况下由金催化的sp 3 –sp 2 C  C 交叉偶联反应。该方法成功的关键是采用带有双（膦基）胺配体的双金属催化剂。提出了一个机制假设，并显示了模型金配合物中可观察到的金属转移、C  Br 氧化加成和 C  C 还原消除。我们预计这种方法将成为开发涉及氧化还原活性金催化剂的新型转化的平台。

  DOI：

  10.1002/anie.201402924
• 作为产物：
  描述：

  5-氯-2-甲基苯并噻唑 、 四羟基二硼 在 甲烷磺酸(2-二环己基膦基-2',4',6'-三-异丙基-1,1'-联苯基)(2'-氨基-1,1'-联苯-2-基)钯(II) 、 三甲基乙酸钾 作用下， 以 2-甲基四氢呋喃 、 甲醇 为溶剂， 反应 4.5h， 生成 2-甲基苯并噻唑-5-硼酸
  参考文献：
  名称：

  钯和镍基体系用于芳基（假）卤化物与B2（OH）4的催化硼化反应。

  摘要：

  尽管在金属催化的芳基（假）卤化物的硼化反应方面取得了最新进展，但仍需要开发出可靠的方法来获得可用于进一步官能化的早期和晚期有机硼中间体。尤其是，在广泛的亲电子伙伴中，在温和的反应条件下运行的通用催化系统的开发仍然难以实现。本文中，我们报道了使用四羟基二硼（B 2（OH）4）进行芳基（假）卤化物直接硼化的三种催化体系（两种基于Pd的体系和一种基于Ni的体系）的开发和应用）。对于基于Pd的催化剂体系，我们已经确定了一般的反应条件，该条件允许通过简单的沉淀来螯合卤离子，从而导致催化剂负载量低至0.01 mol％（100 ppm），反应温度低至室温。我们还描述了一种互补的基于Ni的催化剂体系，该体系采用简单的未连接的Ni（II）盐作为对基于Pd的芳基（假）卤化物进行硼化的体系的廉价替代品。在先进的中间体和原料药上，还证明了将所有三个系统外推至一锅串联硼化/ Suzuki-Miyaura交叉偶联。

  DOI：

  10.1021/acs.joc.0c00929

文献信息

• Design and Synthesis of 5-Aryl-pyridone-carboxamides as Inhibitors of Anaplastic Lymphoma Kinase
  作者：Rongshi Li、Liquan Xue、Tong Zhu、Qin Jiang、Xiaoli Cui、Zheng Yan、Danny McGee、Jian Wang、Vidyasagar Reddy Gantla、Jason C. Pickens、Doug McGrath、Alexander Chucholowski、Stephan W. Morris、Thomas R. Webb

  DOI：10.1021/jm050824x

  日期：2006.2.1

  Anaplastic lymphoma kinase (ALK) is a promising new target for therapy of certain cancers such as anaplastic large-cell lymphoma (ALCL) and inflammatory myofibroblastic tumor (IMT). We have identified a series of novel pyridones as kinase inhibitors of ALK by application of a stepwise process involving in vitro screening of a novel targeted library followed by iterative template modification based

  间变性淋巴瘤激酶（ALK）是治疗某些疾病的新希望靶标，例如间变性大细胞淋巴瘤（ALCL）和炎性肌成纤维细胞瘤（IMT）。我们已通过应用逐步过程确定了一系列新型吡啶酮作为ALK的激酶抑制剂，该过程涉及体外筛选新型靶向库，然后基于药物化学见解和虚拟库的计算排名对模板进行迭代修饰。使用此过程，我们发现了具有增强的效能和选择性的ALK选择性抑制剂。本文讨论了这些新颖的吡啶酮的设计过程和合成细节，以及它们的酶促活性和基于细胞的活性。
• INDANYLOXYDIHYDROBENZOFURANYLACETIC ACIDS
  申请人：ECKHARDT Matthias

  公开号：US20140148462A1

  公开（公告）日：2014-05-29

  The present invention relates to compounds of general formula I, wherein the group (Het)Ar is defined as in claim 1 , which have valuable pharmacological properties, in particular bind to the GPR40 receptor and modulate its activity. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2.

  本发明涉及一般式I的化合物，其中(Het)Ar基团的定义如权利要求1所述，具有有价值的药理特性，特别是与GPR40受体结合并调节其活性。这些化合物适用于治疗和预防可受该受体影响的疾病，如代谢性疾病，特别是2型糖尿病。
• Indanyloxydihydrobenzofuranylacetic acids
  申请人：Eckhardt Matthias

  公开号：US08815864B2

  公开（公告）日：2014-08-26

  The present invention relates to compounds of general formula I, wherein the group (Het)Ar is defined as in claim 1, which have valuable pharmacological properties, in particular bind to the GPR40 receptor and modulate its activity. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2.

  本发明涉及通式I的化合物，其中（Het）Ar基团如权利要求书1所定义，具有有价值的药理特性，特别是结合到GPR40受体并调节其活性。这些化合物适用于治疗和预防可以受到该受体影响的疾病，如代谢性疾病，特别是2型糖尿病。
• Aminative Suzuki–Miyaura coupling
  作者：Polpum Onnuch、Kranthikumar Ramagonolla、Richard Y. Liu

  DOI：10.1126/science.adl5359

  日期：2024.3

  The Suzuki–Miyaura and Buchwald–Hartwig coupling reactions are widely used to form carbon-carbon (C–C) and carbon-nitrogen (C–N) bonds, respectively. We report the incorporation of a formal nitrene insertion process into the Suzuki–Miyaura reaction, altering the products from C–C–linked biaryls to C–N–C–linked diaryl amines and thereby joining the Suzuki–Miyaura and Buchwald–Hartwig coupling pathways

  Suzuki-Miyaura 和 Buchwald-Hartwig 偶联反应分别广泛用于形成碳-碳（C-C）和碳-氮（C-N）键。我们报告了将正式的氮宾插入过程纳入铃木-宫浦反应中，将产物从C-C-连接的联芳基改变为C-N-C-连接的二芳基胺，从而加入铃木-宫浦和Buchwald-Hartwig偶联途径到相同的起始材料类别。钯上的大体积辅助膦配体与市售胺化试剂的组合能够实现芳基卤化物和拟卤化物、硼酸和酯以及许多官能团和杂环的有效反应性。机理见解揭示了成键事件顺序的灵活性，表明胺交叉偶联概念具有扩展的潜力，以涵盖不同的亲核试剂和亲电子试剂以及四组分变体。
• Pd- and Ni-Based Systems for the Catalytic Borylation of Aryl (Pseudo)halides with B₂(OH)₄
  作者：Charissa Munteanu、Taylor E. Spiller、Jun Qiu、Albert J. DelMonte、Steven R. Wisniewski、Eric M. Simmons、Doug E. Frantz

  DOI：10.1021/acs.joc.0c00929

  日期：2020.8.21

  complementary Ni-based catalyst system that employs simple unligated Ni(II) salts as an inexpensive alternative to the Pd-based systems for the borylation of aryl (pseudo)halides. Extrapolation of all three systems to a one-pot tandem borylation/Suzuki–Miyaura cross-coupling is also demonstrated on advanced intermediates and drug substances.

  尽管在金属催化的芳基（假）卤化物的硼化反应方面取得了最新进展，但仍需要开发出可靠的方法来获得可用于进一步官能化的早期和晚期有机硼中间体。尤其是，在广泛的亲电子伙伴中，在温和的反应条件下运行的通用催化系统的开发仍然难以实现。本文中，我们报道了使用四羟基二硼（B 2（OH）4）进行芳基（假）卤化物直接硼化的三种催化体系（两种基于Pd的体系和一种基于Ni的体系）的开发和应用）。对于基于Pd的催化剂体系，我们已经确定了一般的反应条件，该条件允许通过简单的沉淀来螯合卤离子，从而导致催化剂负载量低至0.01 mol％（100 ppm），反应温度低至室温。我们还描述了一种互补的基于Ni的催化剂体系，该体系采用简单的未连接的Ni（II）盐作为对基于Pd的芳基（假）卤化物进行硼化的体系的廉价替代品。在先进的中间体和原料药上，还证明了将所有三个系统外推至一锅串联硼化/ Suzuki-Miyaura交叉偶联。