3,5-二氟-4-甲氧基-苯硼酸 | 208641-98-9

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3,5-二氟-4-甲氧基-苯硼酸
• 中文别名: 3,5-二氟-4-甲氧基苯基硼酸
• 英文名称: (3,5-difluoro-4-methoxyphenyl)boronic acid
• CAS: 208641-98-9
• 化学式: C₇H₇BF₂O₃
• mdl: MFCD08706257
• 分子量: 187.939
• InChiKey: JJRIEFCRGWHLES-UHFFFAOYSA-N

物化性质

• 沸点：
  321.2±52.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  13
• 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：
  49.7
• 氢给体数：
  2
• 氢受体数：
  5

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,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3,5-Difluoro-4-methoxyphenylboronic 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-methoxyphenylboronic acid
CAS number: 208641-98-9

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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, refrigerated.
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: C7H7BF2O3
Molecular weight: 187.9

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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：

  3,5-二氟-4-甲氧基-苯硼酸 、 2-溴-5-(3-甲氧基苯基)噻吩 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 150.0 ℃ 、1.5 MPa 条件下， 反应 0.25h， 以42%的产率得到2-(3,5-difluoro-4-methoxyphenyl)-5-(3-methoxyphenyl)thiophene
  参考文献：
  名称：

  New Insights into the SAR and Binding Modes of Bis(hydroxyphenyl)thiophenes and -benzenes: Influence of Additional Substituents on 17β-Hydroxysteroid Dehydrogenase Type 1 (17β-HSD1) Inhibitory Activity and Selectivity

  摘要：

  17 beta-Hydroxystcroid dehydrogenase type 1 (17 beta-HSD1) is responsible for the catalytic reduction of weakly active E1 to highly potent E2. E2 stimulates the proliferation of hormone-dependent diseases via activation of the estrogen receptor alpha (ER alpha). Because of the overexpression of 17 beta-HSD1 in mammary tumors, this enzyme should be an attractive target for the treatment of estrogen-dependent pathologies. Recently, we have reported on a series of potent 17 beta-HSD1 inhibitors: bis(hydroxyphenyl) azoles, thiophenes, and benzenes. In this paper, different substituents are introduced into the core structure and the biological properties of the corresponding inhibitors are evaluated. Computational methods and analysis of different X-rays of 17 beta-HSD1 lead to identification of two different binding modes for these inhibitors. The fluorine compound 23 exhibits an IC50 of 8 nM and is the most potent nonsteroidal inhibitor described so far. It also shows a high selectivity (17 beta-HSD2, ER alpha) and excellent pharmacokinetic properties after peroral application to rats.

  DOI：

  10.1021/jm901195w
• 作为产物：
  描述：

  3-氯-4-羟基-5-氟苯硼酸 、 4-溴-2,6-二氟苯甲醚 生成 3,5-二氟-4-甲氧基-苯硼酸
  参考文献：
  名称：

  PYRAZOLO [3,4-D] PYRIMIDINE DERIVATIVES USEFUL TO TREAT RESPIRATORY DISORDERS

  摘要：

  本发明涉及式（I）的化合物或其药学上可接受的盐或溶剂，其中R1-R3和Y在说明书中有定义，并且其用于治疗与pi3激酶有关的疾病。

  公开号：

  US20140235632A1

文献信息

• [EN] PYRIDIN-3-YL ACETIC ACID DERIVATIVES AS INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION<br/>[FR] DÉRIVÉS D'ACIDE PYRIDIN-3-YLE ACÉTIQUE UTILISÉS EN TANT QU'INHIBITEURS DE LA RÉPLICATION DU VIRUS DE L'IMMUNODÉFICIENCE HUMAINE
  申请人：VIIV HEALTHCARE UK NO 5 LTD

  公开号：WO2018127800A1

  公开（公告）日：2018-07-12

  Disclosed are compounds of Formula I, including pharmaceutically acceptable salts, pharmaceutical compositions comprising the compounds, methods for making the compounds and their use in inhibiting HIV integrase and treating those infected with HIV or AIDS. (I)

  公开了公式I的化合物，包括药用可接受的盐、包含这些化合物的药物组合物、制备这些化合物的方法，以及它们在抑制HIV整合酶和治疗HIV或艾滋病感染者中的用途。
• The Discovery of a Novel Phosphodiesterase (PDE) 4B-Preferring Radioligand for Positron Emission Tomography (PET) Imaging
  作者：Lei Zhang、Laigao Chen、Elizabeth M. Beck、Thomas A. Chappie、Richard V. Coelho、Shawn D. Doran、Kuo-Hsien Fan、Christopher J. Helal、John M. Humphrey、Zoe Hughes、Kyle Kuszpit、Erik A. Lachapelle、John T. Lazzaro、Chewah Lee、Robert J. Mather、Nandini C. Patel、Marc B. Skaddan、Simone Sciabola、Patrick R. Verhoest、Joseph M. Young、Kenneth Zasadny、Anabella Villalobos

  DOI：10.1021/acs.jmedchem.7b01050

  日期：2017.10.26

  good selectivity over PDE4D, excellent brain permeability, and a high level of specific binding in the “cold tracer” study. In subsequent non-human primate (NHP) PET imaging studies, [18F]8 showed rapid brain uptake and high target specificity, indicating that [18F]8 is a promising PDE4B-preferring radioligand for clinical PET imaging.

  作为我们确定优先选择磷酸二酯酶（PDE）4B的抑制剂以治疗中枢神经系统（CNS）疾病的努力的一部分，我们寻求鉴定正电子发射断层扫描（PET）配体，以实现体内目标占有率的测量。通过系统且经济高效的PET发现过程，包括表达水平（B max）和生物分布测定，PET特异性结构-活性关系（SAR）努力以及使用LC-MS / MS“冷示踪剂”的特异性结合评估方法，我们已经确定8（PF-06445974）是有前途的PET引线。化合物8在“冷示踪剂”研究中，它对PDE4B具有出色的效力，对PDE4D的选择性好，出色的脑通透性和高水平的特异性结合。在随后的非人类灵长类动物（NHP）PET成像研究中，[ 18 F] 8显示出快速的大脑摄取和高靶标特异性，表明[ 18 F] 8是用于临床PET成像的有希望的PDE4B首选放射性配体。
• Synthesis and SAR Studies of 1<i>H</i>-Pyrrolo[2,3-<i>b</i>]pyridine-2-carboxamides as Phosphodiesterase 4B (PDE4B) Inhibitors
  作者：Anish K. Vadukoot、Swagat Sharma、Christopher D. Aretz、Sushil Kumar、Nagsen Gautam、Yazen Alnouti、Amy L. Aldrich、Cortney E. Heim、Tammy Kielian、Corey R. Hopkins

  DOI：10.1021/acsmedchemlett.9b00369

  日期：2020.10.8

  Herein we report the synthesis, SAR, and biological evaluation of a series of 1H-pyrrolo[2,3-b]pyridine-2-carboxamide derivatives as selective and potent PDE4B inhibitors. Compound 11h is a PDE4B preferring inhibitor and exhibited acceptable in vitro ADME and significantly inhibited TNF-α release from macrophages exposed to pro-inflammatory stimuli (i.e., lipopolysaccharide and the synthetic bacterial

  在此，我们报告了一系列 1 H-吡咯并[2,3 - b ]吡啶-2-甲酰胺衍生物作为选择性和有效的 PDE4B 抑制剂的合成、SAR 和生物学评价。化合物11h是 PDE4B 首选抑制剂，表现出可接受的体外ADME，并显着抑制了巨噬细胞暴露于促炎刺激物（即脂多糖和合成细菌脂肽 Pam3Cys）的 TNF-α 释放。此外，11h对一组 CNS 受体具有选择性，并且代表了在 CNS 疾病环境中进一步优化和临床前测试的极好先导。
• 17β-Hydroxysteroid Dehydrogenase Type 1 Inhibition: A Potential Treatment Option for Non-Small Cell Lung Cancer
  作者：Emanuele M. Gargano、Abdelrahman Mohamed、Ahmed S. Abdelsamie、Giuseppe F. Mangiatordi、Hanna Drzewiecka、Paweł P. Jagodziński、Arcangela Mazzini、Chris J. van Koppen、Matthias W. Laschke、Orazio Nicolotti、Angelo Carotti、Sandrine Marchais-Oberwinkler、Rolf W. Hartmann、Martin Frotscher

  DOI：10.1021/acsmedchemlett.1c00462

  日期：2021.12.9

  by non-small cell lung cancer (NSCLC), the present need for new therapeutic approaches is genuine. Up to now, no proof existed that 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) is a viable target for treating this disease. Synthesis of a rationally designed library of 2,5-disubstituted furan derivatives followed by biological screening led to the discovery of 17β-HSD1 inhibitor 1, capable of fully

  面对非小细胞肺癌 (NSCLC) 带来的临床挑战，目前确实需要新的治疗方法。到目前为止，尚无证据表明 1 型 17β-羟基类固醇脱氢酶 (17β-HSD1) 是治疗该病的可行靶点。合成一个合理设计的 2,5-二取代呋喃衍生物库，然后进行生物筛选，发现了 17β-HSD1 抑制剂1，它能够完全抑制人 NSCLC Calu-1 细胞增殖。其药理学特性使其有资格进行进一步的体内研究。研究了1对 17β-HSD2的非常高的选择性，揭示了设计选择性抑制剂的合理方法。17β-HSD1 和1在抗击非小细胞肺癌方面抱有希望。
• GLUCOPYRANOSYL-SUBSTITUTED DIFLUOROBENZYL-BENZENE DERIVATES, MEDICAMENTS CONTAINING SUCH COMPOUNDS, THEIR USE AND PROCESS FOR THEIR MANUFACTURE
  申请人：Eckhardt Matthias

  公开号：US20090318547A1

  公开（公告）日：2009-12-24

  Glucopyranosyl-substituted difluorobenzyl-benzene derivatives of general formula (I) as defined according to claim 1, including the tautomers, the stereoisomers thereof, the mixtures thereof and the salts thereof. The compounds according to the invention are suitable for the treatment of metabolic disorders.

  通式（I）的葡萄糖吡喃基取代的二氟苯基苯衍生物，根据权利要求1所定义，包括其互变异构体、立体异构体、混合物和盐。本发明的化合物适用于治疗代谢紊乱。