3-甲氧基-2-羟基苯硼酸 | 259209-17-1

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 环羧酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 3-甲氧基-2-羟基苯硼酸
• 英文名称: 2-hydroxy-3-methoxyphenyl boronic acid
• 英文别名: (2-Hydroxy-3-methoxyphenyl)boronic acid
• CAS: 259209-17-1
• 化学式: C₇H₉BO₄
• mdl: MFCD08689552
• 分子量: 167.957
• InChiKey: BTYZWLYIOSFCJX-UHFFFAOYSA-N

物化性质

• 沸点：
  356.6±52.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319
• 储存条件：
  -20°C，惰性气体

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 2-Hydroxy-3-methoxyphenylboronic acid
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 2-Hydroxy-3-methoxyphenylboronic acid
CAS number: 259209-17-1

---

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: C7H9BO4
Molecular weight: 168.0

---

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

制备方法与用途

简介

3-甲氧基-2-羟基苯硼酸是一种新型的芳基硼酸类化合物，作为重要的有机合成中间体，在药物合成与修饰、不对称催化剂合成方面具有广泛应用。此外，它还在糖类传感器、物质分离纯化、药物控释系统等领域展现出重要价值。近年来，该化合物在液晶显示材料和农药等领域的应用也日益广泛。

反应信息

• 作为反应物：
  描述：

  3-甲氧基-2-羟基苯硼酸 在 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 Jones reagent 、 四(三苯基膦)钯 、 copper(I) bromide dimethylsulfide complex 、 伯吉斯试剂 、 三氟甲磺酸三甲基硅酯 、 氨 、 水 、 溴 、 氧气 、 lithium 、 sodium hydride 、 二异丁基氢化铝 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 三乙胺 、 间氯过氧苯甲酸 、 sodium hydroxide 、 copper dichloride 、 palladium dichloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 、 苯 为溶剂， 反应 105.08h， 生成 可待因
  参考文献：
  名称：

  可待因的全合成

  摘要：

  本文报道了一种新的合成可待因和吗啡的策略。这种新方法有级联环化以构建二氢呋喃环，和催化的分子内钯Ç  H至安装吗啡喃环体系未活化的脂族烯烃的烯。

  DOI：

  10.1002/chem.201503594
• 作为产物：
  描述：

  木榴油 在 盐酸 、 四甲基乙二胺 、 叔丁基锂 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲基叔丁基醚 、 水 为溶剂， 反应 20.0h， 生成 3-甲氧基-2-羟基苯硼酸
  参考文献：
  名称：

  一种3-甲氧基-2-羟基苯硼酸的制备方法

  摘要：

  本发明涉及一种3‑甲氧基‑2‑羟基苯硼酸的制备方法，主要是通过醚化羟基保护、引入硼酸基和水解脱保护三步反应得到最终产物3‑甲氧基‑2‑羟基苯硼酸。在国内外文献中，该产品的合成相关文献尚未见报道；产品的合成方法简单、易操作，产率较高，为这一类产品的合成提供了理论和实验依据。

  公开号：

  CN107011368A

文献信息

• [EN] PYRROLO-PYRIDINE DERIVATIVES AS ACTIVATORS OF AMPK<br/>[FR] DÉRIVÉS PYRROLO-PYRIDINE UTILISÉS COMME ACTIVATEURS DE L'AMPK
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2011029855A1

  公开（公告）日：2011-03-17

  The present invention relates to pyrrolopyridone compounds of the formula (I), salts thereof, to pharmaceutical compositions containing them and their use in medicine. In particular, the invention relates to compounds as activators of AMPK.

  本发明涉及式(I)的吡咯吡啶酮化合物及其盐，含有它们的药物组合物以及它们在医学上的应用。具体而言，本发明涉及化合物作为AMPK激活剂。
• Fluorescence Study of Imidazoquinoxalines
  作者：Cindy Patinote、Kamel Hadj-Kaddour、Marjorie Damian、Carine Deleuze-Masquéfa、Pierre Cuq、Pierre-Antoine Bonnet

  DOI：10.1007/s10895-017-2097-z

  日期：2017.9

  The fluorescence properties of eleven novel derivatives based on the imidazo[1,2-a]quinoxaline structures have been studied. The absorption and emission spectra of these compounds have been recorded in dimethylsulfoxide solution. The phenyl substituting group on position 1 gives them particular properties thanks to the diverse hydroxy or methoxy decorating moieties, especially when they are multiplied

  研究了基于咪唑并[1,2- a ]喹喔啉结构的11种新型衍生物的荧光性质。这些化合物的吸收和发射光谱已在二甲基亚砜溶液中记录。由于不同的羟基或甲氧基装饰部分，尤其是当它们被混合或混合时，位置1上的苯基取代基赋予它们特殊的性能。研究的荧光自动猝灭表明，荧光强度的降低仅与芳族化合物的化学结构相关。
• New imidazoquinoxaline derivatives: Synthesis, biological evaluation on melanoma, effect on tubulin polymerization and structure–activity relationships
  作者：Zahraa Zghaib、Jean-François Guichou、Johanna Vappiani、Nicole Bec、Kamel Hadj-Kaddour、Laure-Anaïs Vincent、Stéphanie Paniagua-Gayraud、Christian Larroque、Georges Moarbess、Pierre Cuq、Issam Kassab、Carine Deleuze-Masquéfa、Mona Diab-Assaf、Pierre-Antoine Bonnet

  DOI：10.1016/j.bmc.2016.04.004

  日期：2016.6

  compounds show significant antiproliferative activity with IC50 in the range of 0.077–122 μM against human melanoma cell line (A375). Direct inhibition of tubulin polymerization assay in vitro is also assessed. Results show that compounds 6b, 6e, 6g, and EAPB0503 highly inhibit tubulin polymerization with percentages of inhibition of 99%, 98%, 90%, and 84% respectively. Structure–activity relationship

  微管被认为是抗癌治疗的重要目标。EAPB0503及其结构咪唑并[1,2- a ]喹喔啉衍生物是具有有效抗癌活性的主要微管干扰剂。在这项研究中，描述了几种新的EAPB0503衍生物的合成，并报道了13种新衍生物对A375人黑素瘤细胞系的抗癌作用。所有新化合物对人黑素瘤细胞系（A375）的IC 50均显示出显着的抗增殖活性，其IC 50值为0.077–122μM。还评估了体外对微管蛋白聚合测定的直接抑制。结果表明，化合物6b，6e，6g和EAPB0503高度抑制微管蛋白的聚合，抑制百分比分别为99％，98％，90％和84％。该系列中的结构-活性关系研究也与微管蛋白秋水仙碱结合位点的分子对接研究进行了讨论。
• General Methods for Synthesis of<i>N</i>-Methyliminodiacetic Acid Boronates from Unstable<i>ortho</i>-Phenolboronic Acids
  作者：Su-Jin Ahn、Chun-Young Lee、Cheol-Hong Cheon

  DOI：10.1002/adsc.201301023

  日期：2014.5.26

  A range of N‐methyliminodiacetic acid (MIDA) boronates of commercially available but unstable ortho‐phenolboronic acid derivatives can be readily prepared through simple condensation between the corresponding phenolboronic acids and MIDA in the presence of molecular sieves. The resulting MIDA boronates are bench‐top stable and display a remarkable stability even in DMSO solution at high temperature

  在分子筛存在下，通过相应的酚硼酸和MIDA之间的简单缩合，可以很容易地制得一系列市售的N-甲基亚氨基二乙酸（MIDA）硼酸盐，但不稳定的邻苯酚硼酸衍生物。所得的MIDA硼酸盐与它们的母体硼酸相比，具有台式稳定性，即使在高温（> 120°C）的DMSO溶液中也显示出显着的稳定性。此外，使用缓释方案在交叉偶联反应中成功证明了所得MIDA硼酸酯的效用，与其母体硼酸同类产品相比，交联产物的收率要高得多。此外，另一种难以访问的合成途径却更加有效邻-苯酚MIDA硼酸酯已经通过保护MIDA硼酸酯的形成甲氧基甲基的（MOM）开发邻-phenolboronic酸，随后在环境条件下用的TMSCl的MOM基团脱保护。
• [EN] PYRROLO [3, 2 -D] PYRIMIDIN-3 -YL DERIVATIVES USED AS ACTIVATORS OF AMPK<br/>[FR] DÉRIVÉS PYRROLO [3,2-D] PYRIMIDIN-3-YLE UTILISÉS COMME ACTIVATEURS DE L'AMPK
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2011138307A1

  公开（公告）日：2011-11-10

  The present invention relates to pyrrolopyrimidones compounds of the formula (I), salts thereof, to pharmaceutical compositions containing them and their use in medicine. In particular, the invention relates to compounds as activators of AMPK.

  本发明涉及式(I)的吡咯吡咪酮化合物及其盐，包含它们的药物组合物以及它们在医学上的应用。具体来说，本发明涉及化合物作为AMPK激活剂。