4,5-二甲氧基-2-(甲氧基羰基)苯硼酸频那醇酯 | 1201566-80-4

• 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: 4,5-二甲氧基-2-(甲氧基羰基)苯硼酸频那醇酯
• 中文别名: 4,5-二甲氧基-2-(甲氧基羰基)苯基硼酸频哪醇酯
• 英文名称: 2-pinacolboranyl-4,5-dimethoxybenzoic acid methyl ester
• 英文别名: Methyl 4,5-dimethoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
• CAS: 1201566-80-4
• 化学式: C₁₆H₂₃BO₆
• 分子量: 322.166
• InChiKey: TUPWLISYCDGHEO-UHFFFAOYSA-N

物化性质

• 沸点：
  440.1±45.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 4,5-Dimethoxy-2-(methoxycarbonyl)phenylboronic acid pinacol ester
Synonyms: Methyl 4,5-dimethoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 4,5-Dimethoxy-2-(methoxycarbonyl)phenylboronic acid pinacol ester
CAS number: 1201566-80-4

---

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: C16H23BO6
Molecular weight: 322.2

---

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

---

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：

  5-nitro-6-O-trifluoromethanesulfonyloxy-quinoline 、 4,5-二甲氧基-2-(甲氧基羰基)苯硼酸频那醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 Methyl 4,5-dimethoxy-2-(5-nitroquinolin-6-yl)benzoate
  参考文献：
  名称：

  N-取代的苯并[ c ]菲咯啉和苯并[ c ]菲咯啉酮类抗增殖剂的合成及生物学评价

  摘要：

  分别合成了在位置N5和C6处被二烷基氨基烷基侧链取代的苯并[ c ]菲咯啉和苯并[ c ]菲咯啉酮，并对其生物学活性进行了评估。他们表现出与某些DNA相互作用有关的间质细胞毒性。但是，低的拓扑异构酶1亲和力表明其他细胞靶标负责抗增殖活性。

  DOI：

  10.1016/j.ejmech.2011.02.065
• 作为产物：
  描述：

  2-溴-4,5-二甲氧基苯甲酸甲酯 、 频那醇硼烷 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 生成 4,5-二甲氧基-2-(甲氧基羰基)苯硼酸频那醇酯
  参考文献：
  名称：

  N-取代的苯并[ c ]菲咯啉和苯并[ c ]菲咯啉酮类抗增殖剂的合成及生物学评价

  摘要：

  分别合成了在位置N5和C6处被二烷基氨基烷基侧链取代的苯并[ c ]菲咯啉和苯并[ c ]菲咯啉酮，并对其生物学活性进行了评估。他们表现出与某些DNA相互作用有关的间质细胞毒性。但是，低的拓扑异构酶1亲和力表明其他细胞靶标负责抗增殖活性。

  DOI：

  10.1016/j.ejmech.2011.02.065

文献信息

• Synthesis of N-substituted benzo[c][1,7]- and benzo[c][1,8] phenanthrolin-(5H)-6-ones through a Pd-mediated Suzuki–Miyaura heteroaryl-aryl coupling reaction
  作者：Constance Genès、Sylvie Michel、François Tillequin、François-Hugues Porée

  DOI：10.1016/j.tet.2009.09.110

  日期：2009.11

  In the course of the search for non-camptothecin topoisomerase I inhibitors we have undertaken the synthesis of N-substituted benzo[c][1,7]- and benzo[c][1,8]phenanthrolinone derivatives. An intermolecular Suzuki–Miyaura heteroaryl-aryl coupling reaction was planned as the key step. Then a nitro reduction followed by a concomitant lactamization achieved the construction of the tetracycle structures

  在寻找非喜树碱拓扑异构酶I抑制剂的过程中，我们进行了N-取代的苯并[ c ] [1,7]-和苯并[ c ] [1,8]菲咯啉酮衍生物的合成。分子间的铃木-宫浦杂芳基-芳基偶联反应被计划为关键步骤。然后硝基还原，随后伴随内酰胺化，实现了四环结构的构建。这种方法可以快速有效地制备生物有效的化合物。
• Convergent Total Syntheses of the Amaryllidaceae Alkaloids Lycoranine A, Lycoranine B, and 2-Methoxypratosine
  作者：Hye Sun Kim、Martin G. Banwell、Anthony C. Willis

  DOI：10.1021/jo4006987

  日期：2013.5.17

  and 3 respectively, have been prepared in a convergent manner by two related routes. The superior one involves C–H functionalization of the relevant 5-methoxyindole at C-7 using Hartwig’s protocol and thus forming the corresponding borolated indole that could be coupled with the requisite 2-bromobenzoate to deliver the title natural products. Single crystal X-ray analyses of the synthetically derived

  标题生物碱，1，2，和3已经分别以会聚的方式通过两个相关的途径制备。上等产品涉及使用Hartwig的规程在C-7处将相关的5-甲氧基吲哚进行C–H官能化，从而形成相应的硼化吲哚，可与必需的2-溴苯甲酸酯偶联以提供标题的天然产物。报道了化合物1和2的合成衍生样品的单晶X射线分析。
• Total Synthesis and Structure–Activity Relationship Studies of Phelligridins C and D, and Phellifuropyranone A
  作者：Takayuki Ohyoshi、Keisuke Mitsugi、Fumitaka Ichimura、Tatsuya Higuma、Masahito Yoshida、Hideo Kigoshi

  DOI：10.1246/bcsj.20200212

  日期：2020.12.15

  α-Pyrone polyphenols, phelligridins C and D (meshimakobnols B and A), and phellifuropyranone A, isolated from a Japanese mushroom, are growth inhibitors of cancer cells. Herein, we report full deta...

  α-吡喃酮多酚、草甘膦 C 和 D（meshimakobnols B 和 A），以及从日本蘑菇中分离出来的 phellifuropyranone A 是癌细胞的生长抑制剂。在这里，我们报告完整的细节...
• Catalytic and Base‐free Suzuki‐type α‐Arylation of Cyclic 1,3‐Dicarbonyls via a Cyclic Iodonium Ylide Strategy
  作者：Mingxuan Liang、Mengling He、Zhiqing Zhong、Bei Wan、Qingfeng Du、Shaoyu Mai

  DOI：10.1002/anie.202400741

  日期：2024.4.22

  A general and catalytic α-arylation of cyclic 1,3-dicarbonyls have been developed, providing expedient access toward a wide range of high-value 2-aryl (hetero)cyclic 1,3-dicarbonyls. The key to success is through a cyclic iodonium ylide strategy. Our approach is base-free and exhibits broad substrate scope (>100 examples). Importantly, our approach allows late-stage modification and significantly simplifying

  环状 1,3-二羰基的通用催化 α-芳基化已经开发出来，为获得各种高价值的 2-芳基（杂）环 1,3-二羰基提供了便利。成功的关键是通过环状碘叶立德策略。我们的方法是无碱基的，并且具有广泛的底物范围（> 100 个示例）。重要的是，我们的方法允许后期修改并显着简化先前的合成。
• Palladium-catalyzed synthesis of indenoindoles via C-H activation and tandem synthesis of indenoisoquinolines via Suzuki-Miyaura coupling and annulation
  作者：Vijaykumar Naik、Faiz Ahmed Khan

  DOI：10.24820/ark.5550190.p012.095

  日期：——