2-(2,5-二甲氧基苯基)-4,4,5,5-四甲基-1,3,2-二噁硼烷 | 1073339-07-7

• 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: 2-(2,5-二甲氧基苯基)-4,4,5,5-四甲基-1,3,2-二噁硼烷
• 中文别名: 2,5-二甲氧基苯基硼酸,频哪醇酯；2,5-二甲氧基苯硼酸频哪醇酯
• 英文名称: 2-(2,5-dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1073339-07-7
• 化学式: C₁₄H₂₁BO₄
• 分子量: 264.129
• InChiKey: XJCGLLQYWCVCSS-UHFFFAOYSA-N

物化性质

• 熔点：
  58-60 °C
• 沸点：
  376.3±32.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  36.9
• 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：
  应存放在室温、干燥且密封的环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2,5-Dimethoxyphenylboronic acid, pinacol ester
Synonyms: 2-(2,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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

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Section 3. Composition/information on ingredients.
Ingredient name: 2,5-Dimethoxyphenylboronic acid, pinacol ester
CAS number: 1073339-07-7

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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.

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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.

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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.

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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.
Storage:

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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.

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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: C14H21BO4
Molecular weight: 264.1

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

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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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.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-(2,5-二甲氧基苯基)-4,4,5,5-四甲基-1,3,2-二噁硼烷 、 (R)-7-bromo-3-methyl-5-(1-(4-(trifluoromethyl)phenyl)ethyl)isoxazolo[4,5-d]pyridazin-4(5H)-one 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 以9%的产率得到7-(2,5-dimethoxyphenyl)-3-methyl-5-{(1R)-1-[4-(trifluoromethyl)phenyl]ethyl}[1,2]oxazolo[4,5-d]pyridazin-4(5H)-one
  参考文献：
  名称：

  SUBSTITUTED ISOXAZOLOPYRIDAZINONES AND ISOTHIAZOLOPYRIDAZINONES AND METHODS OF USE

  摘要：

  式(I)的化合物及其药用盐，其中R1、R2和R3如规范中定义的那样，可用于治疗通过或通过正向变构调节γ-氨基丁酸B（GABA-B）受体预防或改善的症状或疾病。描述了制备这些化合物的方法。还描述了式(I)的化合物的药物组合物，以及使用这些化合物和组合物的方法。

  公开号：

  US20170073353A1
• 作为产物：
  描述：

  1-氯-3,5-二甲氧基苯 在 palladium diacetate 、 三乙胺 、 potassium iodide 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 反应 4.0h， 生成 2-(2,5-二甲氧基苯基)-4,4,5,5-四甲基-1,3,2-二噁硼烷
  参考文献：
  名称：

  Method for preparing aminoarylborane compounds or derivatives thereof

  摘要：

  本发明提供了一种制备氨基芳基硼化合物及其衍生物的方法，包括通过在催化体系存在下，将芳基氯化物与氨基硼烷化合物反应进行芳基化的步骤。通常，该转化包括将芳基氯化物Ar-Cl与氨基硼烷化合物反应，转化为以下式的氨基芳基硼化合物：

  公开号：

  EP2881398A1

文献信息

• <i>Ortho</i>-Selective C–H Borylation of Aromatic Ethers with Pinacol-borane by Organo Rare-Earth Catalysts
  作者：Can Xue、Yong Luo、Huailong Teng、Yuanhong Ma、Masayoshi Nishiura、Zhaomin Hou

  DOI：10.1021/acscatal.8b01364

  日期：2018.6.1

  borylation of aromatic ethers such as anisoles is of much interest and importance, but has remained a challenge to date. We report herein the catalytic ortho-selective C–H borylation of a wide range of aromatic ethers with pinacolborane (HBpin) by rare-earth metallocene complexes. This protocol offers an efficient and straightforward route for the synthesis of a variety of borylated aromatic ether derivatives

  芳族醚（如茴香醚）的区域选择性C–H硼化非常令人关注和重要，但迄今为止仍是一个挑战。我们在这里报告了稀土金属茂配合物与频哪醇硼烷（HBpin）催化的各种芳族醚的邻位选择性C–H硼化反应。该方案为合成各种硼酸化的芳族醚衍生物提供了一种有效而直接的途径。发现用于稀土金属催化剂的合适的金属/配体组合对于促进这种转化至关重要。
• Nano-Fe2O3-catalyzed direct borylation of arenes
  作者：Guobing Yan、Yubo Jiang、Chunxiang Kuang、Shuai Wang、Haichao Liu、Yan Zhang、Jianbo Wang

  DOI：10.1039/b926945b

  日期：——

  Nano-Fe2O3-catalyzed borylation of arenes with diboron pinacol ester B2pin2 has been found to give borylation products with selectivity controlled by electronic effects of substituents.

  纳米-Fe2O3催化的芳烃与双屏醇双硼酯B2pin2的硼化反应已被发现能生成受取代基电子效应调控选择性的硼化产物。
• 一种通过钯催化未活化烯烃的串联Heck/Suzuki偶联反应
  申请人：复旦大学

  公开号：CN112694440B

  公开（公告）日：2022-06-14

  本发明提供了一种通过钯催化未活化烯烃的串联Heck/Suzuki偶联反应，属于有机合成领域。因为本发明提出以化合物R3‑Bpin为原料，以Pd2(dba)3·CHCl3为催化剂，以为配体，以Cs2CO3为碱，用甲苯做溶剂来合成内酰胺产物，所以本发明通过钯催化的不对称串联Heck/Suzuki偶联反应实现了未活化烯烃的高对映选择性的双官能团化反应，同时在温和的条件下以良好的产率构建了一系列具有手性全碳季碳中心的苯稠环骨架，是一系列天然产物中重要的结构单元，具有广泛的应用价值。
• Pd-Catalyzed Enantioselective Dicarbofunctionalization of Alkene to Access Disubstituted Dihydroisoquinolinone
  作者：Qiaoyu Chen、Sanliang Li、Xiaoxiao Xie、Hao Guo、Junfeng Yang、Junliang Zhang

  DOI：10.1021/acs.orglett.1c00974

  日期：2021.6.4

  A Pd/Xu-Phos-catalyzed asymmetric Heck/Suzuki domino reaction has been developed that shows high functional group tolerance and enables coupling with various aryl/alkenyl borates. A series of chiral disubstituted dihydroisoquinolinones could be obtained in good yields and excellent enantioselectivities.

  已开发出 Pd/Xu-Phos 催化的不对称 Heck/Suzuki 多米诺反应，该反应显示出高官能团耐受性并能够与各种芳基/烯基硼酸酯偶联。可以以良好的收率和优异的对映选择性获得一系列手性双取代二氢异喹啉酮。
• Borylation of Unactivated Aryl Chlorides under Mild Conditions by Using Diisopropylaminoborane as a Borylating Reagent
  作者：Hélène D. S. Guerrand、Ludovic D. Marciasini、Mélissa Jousseaume、Michel Vaultier、Mathieu Pucheault

  DOI：10.1002/chem.201304861

  日期：2014.5.5

  The synthesis of arylboronic ester derivatives from aryl chlorides by using aryl(amino)boranes is described. Palladium‐catalyzed coupling between aryl chlorides and diisopropylaminoborane leads to the formation of a CB bond under mild conditions. A wide range of functional groups are tolerated, making this method particularly useful for the borylation of functionalized aromatics.

  描述了通过使用芳基（氨基）硼烷从芳基氯化物合成芳基硼酸酯衍生物。在温和条件下，芳基氯化物和二异丙基氨基硼烷之间的钯催化偶联导致形成CB键。宽泛的官能团是可以容忍的，这使得该方法对官能化芳族化合物的硼酸酯化特别有用。