4-硼-2,6-二氟苯甲酸 | 1029716-94-6

• 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 - 苯和取代衍生物
• 中文名称: 4-硼-2,6-二氟苯甲酸
• 中文别名: 3,5-二氟-4-羧酸苯基硼酸
• 英文名称: 3,5-difluoro-4-carboxyphenylboronic acid
• 英文别名: 4-borono-2,6-difluorobenzoic acid
• CAS: 1029716-94-6
• 化学式: C₇H₅BF₂O₄
• 分子量: 201.922
• InChiKey: AWIXNRNZROUJQB-UHFFFAOYSA-N

物化性质

• 沸点：
  383.8±52.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.66
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3,5-Difluoro-4-carboxyphenylboronic acid
Synonyms:

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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: 3,5-Difluoro-4-carboxyphenylboronic acid
CAS number: 1029716-94-6

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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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C7H5BF2O4
Molecular weight: 201.9

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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, hydrogen fluoride.

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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：

  4-硼-2,6-二氟苯甲酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 氯仿 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 三氟乙酸 为溶剂， 反应 97.0h， 生成 1-(1-(4-borono-2,6-difluorophenyl)-1,12-dioxo-5,8-dioxa-2,11-diazaheptadecan-17-yl)-3,3-dimethyl-5-sulfo-2-((1E,3E)-5-((E)-1,3,3-trimethyl-5-sulfoindolin-2-ylidene)penta-1,3-dien-1-yl)-3H-indol-1-ium
  参考文献：
  名称：

  由合成聚合物和工程细菌孢子的可编程组装实现的催化材料

  摘要：

  天然生物材料通过自组装过程形成并催化多种反应。在这里，我们报告了一种由设计的合成聚合物与工程细菌孢子组成的可编程分子组装体。这种自组装过程是由孢子表面聚糖上动态共价键形成驱动的，并产生结构稳定、自修复和可回收的宏观材料。聚合物物种的分子编程塑造了这些材料的物理特性，而代谢休眠孢子允许长期环境储存。将孢子与基因编码的功能相结合，可以实现操作简单且重复的酶催化。我们的工作将分子和基因工程结合起来，为可持续生物催化提供可扩展和可编程的稳健材料合成。

  DOI：

  10.1021/jacs.3c05153
• 作为产物：
  描述：

  3,5-二氟-4-甲酰基苯基硼酸 在 potassium permanganate 作用下， 生成 4-硼-2,6-二氟苯甲酸
  参考文献：
  名称：

  Ortho-substituted aryl monoboronic acids have improved selectivity for d-glucose relative to d-fructose and l-lactate

  摘要：

  Ortho-substituted aryl monoboronic acids have been found to have improved selectivity for D-glucose compared to D-fructose and L-lactate. These findings are supported by computational studies on the B3LYP/6-31G(d) level using Gaussian. This finding is of interest for development of boronate based D-glucose sensors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.062

文献信息

• [EN] INHIBITORS OF WDR5 PROTEIN-PROTEIN BINDING<br/>[FR] INHIBITEURS DE LA LIAISON PROTÉINE WDR5-PROTÉINE
  申请人：ONTARIO INST FOR CANCER RES (OICR)

  公开号：WO2017147700A1

  公开（公告）日：2017-09-08

  The present application is directed to compounds of Formula I: compounds comprising these compounds and their uses, for example as medicaments for the treatment of diseases, disorders or conditions mediated or treatable by inhibition of binding between WDR5 protein and its binding partners.

  本申请涉及到Formula I的化合物：包括这些化合物的化合物及其用途，例如作为治疗由于抑制WDR5蛋白与其结合伙伴之间结合而介导或可治疗的疾病、疾病或症状的药物。
• Importance of Binding Site Hydration and Flexibility Revealed When Optimizing a Macrocyclic Inhibitor of the Keap1–Nrf2 Protein–Protein Interaction
  作者：Fabio Begnini、Stefan Geschwindner、Patrik Johansson、Lisa Wissler、Richard J. Lewis、Emma Danelius、Andreas Luttens、Pierre Matricon、Jens Carlsson、Stijn Lenders、Beate König、Anna Friedel、Peter Sjö、Stefan Schiesser、Jan Kihlberg

  DOI：10.1021/acs.jmedchem.1c01975

  日期：2022.2.24

  Upregulation of the transcription factor Nrf2 by inhibition of the interaction with its negative regulator Keap1 constitutes an opportunity for the treatment of disease caused by oxidative stress. We report a structurally unique series of nanomolar Keap1 inhibitors obtained from a natural product-derived macrocyclic lead. Initial exploration of the structure-activity relationship of the lead, followed

  通过抑制与其负调节因子 Keap1 的相互作用来上调转录因子 Nrf2 构成了治疗由氧化应激引起的疾病的机会。我们报告了从天然产物衍生的大环铅中获得的一系列结构独特的纳摩尔级 Keap1 抑制剂。对先导化合物的构效关系进行初步探索，然后进行结构导向优化，使抑制效力提高了 100 倍。纳摩尔抑制剂的大环核心定位三个药效团单元，用于与 Keap1 的关键残基（包括 R415、R483 和 Y572）进行有效相互作用。配体优化导致配位水分子从 Keap1 结合位点移位，并显着改变热力学曲线。此外，R415 和 R483 的微小重组伴随着配体之间亲和力的重大差异。因此，本研究表明在设计高亲和力配体时考虑 Keap1 结合位点的水合作用和灵活性的重要性。
• Revisiting the Quinoxalinedione Scaffold in the Construction of New Ligands for the Ionotropic Glutamate Receptors
  作者：Charles S. Demmer、David Rombach、Na Liu、Birgitte Nielsen、Darryl S. Pickering、Lennart Bunch

  DOI：10.1021/acschemneuro.7b00243

  日期：2017.11.15

  among the AMPA, NMDA, and KA receptors, and to some extent also obtain full receptor subtype selectivity. Highlights of the study of 44 new analogues are compound 2m being a high affinity ligand for native AMPA receptors (IC50= 0.48 μM), analogues 2e,f,h,k,v all displayed selectivity for native NMDA receptors, and compounds 2s,t,u are selective ligand for the GluK1 receptor. Most interestingly, compound

  二十多年前，喹喔啉二酮支架被证明是α-氨基酸的生物等排体。经过广泛的结构-活性关系（SAR）研究，在离子型谷氨酸受体领域确定了拮抗剂DNQX，CNQX和NBQX。在这项工作中，我们将重新研究喹喔啉二酮支架，并探索在6位上引入酸官能团的方法。SAR研究表明，通过这种策略，可以调节AMPA，NMDA和KA受体之间的iGluR选择性，并且在某种程度上还可以获得完全的受体亚型选择性。研究44个新类似物的重点是化合物2m是天然AMPA受体的高亲和力配体（IC 50 = 0.48μM），类似物2e，f，h，k，v均显示出对天然NMDA受体的选择性，化合物2s，t，u是GluK1受体的选择性配体。最有趣的是，化合物2w被证明是GluK3优先配体，对天然AMPA，KA和NMDA受体具有完全选择性。