3-氟-2-羟基苯硼酸 | 259209-24-0

• 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-氟-2-羟基苯硼酸
• 英文名称: (3-fluoro-2-hydroxyphenyl)boronic acid
• CAS: 259209-24-0
• 化学式: C₆H₆BFO₃
• mdl: MFCD07781238
• 分子量: 155.921
• InChiKey: UOYUUFBFEICSRZ-UHFFFAOYSA-N

物化性质

• 沸点：
  308.7±52.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.7
• 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：
  P233,P260,P261,P264,P270,P271,P280,P301+P312,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P330,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 3-Fluoro-2-hydroxyphenylboronic acid
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 3-Fluoro-2-hydroxyphenylboronic acid
CAS number: 259209-24-0

---

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.
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: C6H6BFO3
Molecular weight: 155.9

---

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

---

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：

  3-氟-2-羟基苯硼酸 以 二甲基亚砜 为溶剂， 反应 18.0h， 以91%的产率得到2-氟苯酚
  参考文献：
  名称：

  Protodeboronation of ortho- and para-Phenol Boronic Acids and Application to ortho and meta Functionalization of Phenols Using Boronic Acids as Blocking and Directing Groups

  摘要：

  The first metal-free thermal protodeboronation of ortho- and para-phenol boronic acids in DMSO was developed. The protodeboronation was successfully applied to the synthesis of ortho- and meta-functionalized phenols using the boronic acid moiety as a blocking group and a directing group, respectively. Mechanistic studies suggested that this protodeboronation proceeds through the coordination of water to the boron atom followed by sigma-bond metathesis.

  DOI：

  10.1021/jo402174v
• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 3-氟-2-羟基苯硼酸
  参考文献：
  名称：

  铑 (II) 催化二茂铁与 CO2 的 C-H 羧化反应

  摘要：

  二氧化碳 (CO 2 ) 被认为是绿色和可再生的 C1 原料。然而，由于其热力学和动力学稳定性，过渡金属催化未活化的 C-H 键与 CO 2的羧化反应仍然具有挑战性。在此，报道了 Rh( II ) 催化和 CO 2参与的二茂铁衍生物环戊二烯基 (Cp) 环惰性 sp 2 C-H 键羧化反应的方案，该方案产生了一系列重要的二茂铁嵌入内酯广泛用于药物或配体的分子骨架。此外，使用手性 NHC 配体实现了适度的对映选择性，这可以被视为与 CO 2进行不对称 C-H 羧化的第一个例子. 初步的机理实验支持二价铑作为真正的活性催化剂，并据此提出了合理的催化循环。

  DOI：

  10.1039/d2gc04337h

文献信息

• Small Molecule Inhibitors of KRAS G12C Mutant
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20210122764A1

  公开（公告）日：2021-04-29

  The disclosure provides compounds of Formula (I) or a pharmaceutically acceptable salt thereof, wherein W 1 , W 2 , Y, Z, M, L, C y , C z , R 1 , R 2 , R 3 , R 4 , R 2a , R y , R z and the subscripts m, n, q, and r are as described herein. The compounds or their pharmaceutically acceptable salts can inhibit the G12C mutant of Kirsten rat sarcoma (KRAS) protein and are expected to have utility as therapeutic agents, for example, for treating cancer. The disclosure also provides pharmaceutical compositions which comprise compounds of Formula (I) or pharmaceutically acceptable salts thereof. The disclosure also relates to methods for use of the compounds or their pharmaceutically acceptable salts in the therapy and prophylaxis of cancer and for preparing pharmaceuticals for this purpose.

  该披露提供了Formula (I)的化合物或其药用盐，其中W1、W2、Y、Z、M、L、Cy、Cz、R1、R2、R3、R4、R2a、Ry、Rz以及下标m、n、q和r如本文所述。这些化合物或其药用盐可以抑制Kirsten大鼠肉瘤（KRAS）蛋白的G12C突变体，并有望作为治疗剂具有用途，例如用于治疗癌症。该披露还提供了包含Formula (I)的化合物或其药用盐的药物组合物。该披露还涉及使用这些化合物或其药用盐在癌症的治疗和预防中的方法，以及为此目的制备药物。
• [EN] COMPOUNDS AND THEIR USE AS INHIBITORS OF N-MYRISTOYL TRANSFERASE<br/>[FR] COMPOSÉS ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE LA N-MYRISTOYL TRANSFÉRASE
  申请人：IMP INNOVATIONS LTD

  公开号：WO2017001812A1

  公开（公告）日：2017-01-05

  This invention provides compounds of formula (I) and salts thereof, which have activity as inhibitors of N-myristoyl transferase (NMT). The invention also relates to uses of such compounds as medicaments, in particular in the treatment of a disease or disorder in which inhibition of N-myristoyl transferase provides a therapeutic or prophylactic effect, including protozoan infections (such as malaria and leishmaniasis), viral infections (such as human rhinovirus and HIV), and hyperproliferative disorders (such as B-cell lymphoma).

  这项发明提供了式（I）的化合物及其盐，具有作为N-肉豆蔻酰转移酶（NMT）抑制剂的活性。该发明还涉及将这类化合物用作药物的用途，特别是在治疗需要抑制N-肉豆蔻酰转移酶以产生治疗或预防效果的疾病或紊乱中，包括原虫感染（如疟疾和利什曼病）、病毒感染（如人类鼻病毒和HIV）以及高增殖性疾病（如B细胞淋巴瘤）。
• One-Pot Generation of Functionalized Benzynes from Readily Available 2-Hydroxyphenylboronic Acids
  作者：Takashi Ikawa、JingKai Sun、Akira Takagi、Shuji Akai

  DOI：10.1021/acs.joc.9b03169

  日期：2020.3.6

  We developed a one-pot method for the generation of benzynes from a range of readily available 2-hydroxyphenylboronic acids. This method features the in situ activation of both boronic acid and hydroxyl groups of the substrate to enhance benzyne generation at 60 °C. Such mild conditions facilitate the generation of functionalized benzynes that immediately react with diverse arynophiles to produce multisubstituted

  我们开发了一种一锅法，可从一系列容易获得的2-羟基苯基硼酸中生成苯炔。该方法的特点是原位活化硼酸和底物的羟基，以增强60°C下苯并炔的生成。这种温和的条件促进了官能化的苯并炔的生成，该苯并炔立即与各种亲核体反应生成多取代的稠合苯。
• [EN] MONOCYCLIC HETEROARYL SUBSTITUTED COMPOUNDS<br/>[FR] COMPOSÉS HÉTÉROARYLE MONOCYCLIQUE SUBSTITUÉS
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2018013772A1

  公开（公告）日：2018-01-18

  Disclosed are compounds of Formulas (I), (II), (III), (IV), (V), (VI), (VII), or (VIII): (I) (II) (III) (IV) (V) (VI) (VII) (VIII) or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate or prodrug thereof, wherein R3 is a monocyclic heteroaryl group substituted with zero to 3 R3a; and R1, R2, R3a, R4, and n are defined herein. Also disclosed are methods of using such compounds as PAR4 inhibitors, and pharmaceutical compositions comprising such compounds. These compounds are useful in inhibiting or preventing platelet aggregation, and are useful for the treatment of a thromboembolic disorder or the primary prophylaxis of a thromboembolic disorder.

  公开的是Formula（I）、（II）、（III）、（IV）、（V）、（VI）、（VII）或（VIII）的化合物：（I）（II）（III）（IV）（V）（VI）（VII）（VIII）或其立体异构体、互变异构体、药学上可接受的盐、溶剂合物或前药，其中R3是一个单环杂环芳基基团，其上取代零至3个R3a；R1、R2、R3a、R4和n在此处有定义。还公开了将这些化合物用作PAR4抑制剂的方法，以及包含这些化合物的药物组合物。这些化合物在抑制或预防血小板聚集方面很有用，并且可用于治疗血栓栓塞性疾病或血栓栓塞性疾病的初级预防。
• 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。