3-氟吡啶-4-硼酸 | 458532-97-3

• 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 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 3-氟吡啶-4-硼酸
• 中文别名: 3-氟-4-吡啶硼酸
• 英文名称: 3-fluoro-4-pyridylboronic acid
• 英文别名: (3-fluoropyridin-4-yl)boronic acid；3-fluoropyridine-4-boronic acid
• CAS: 458532-97-3
• 化学式: C₅H₅BFNO₂
• 分子量: 140.91
• InChiKey: QUHSESYLMZVXCN-UHFFFAOYSA-N

物化性质

• 熔点：
  237-239
• 沸点：
  289.0±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  10
• 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：
  53.4
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25,S26,S39
• 危险类别码：
  R37/38,R41
• 海关编码：
  2933399090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请保持冷静。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Fluoropyridine-4-boronic acid
Synonyms: 3-Fluoro-4-pyridineboronic acid; 3-Fluoropyridin-4-ylboronic acid

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H318: Causes serious eye damage
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 3-Fluoropyridine-4-boronic acid
CAS number: 458532-97-3

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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, under −20◦C.
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
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C5H5BFNO2
Molecular weight: 140.9

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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, nitrogen oxides, 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-氟吡啶-4-硼酸 在 copper(ll) sulfate pentahydrate 、 鞣花酸 作用下， 以 甲醇 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 以75%的产率得到3-氟吡啶-4-醇
  参考文献：
  名称：

  Oxidative hydroxylation of arylboronic acids to phenols catalyzed by copper nanoparticles ellagic acid composite

  摘要：

  Copper nanoparticles (Cu NPs) were prepared by in situ reduction of CuSO4 center dot 5H(2)O using ellagic acid (EA) as the reducing agent as well as stabilizer and its catalytic activity is tested in the oxidative hydroxylation of phenylboronic acids to phenol without any added base or ligand. The synthesized Cu NPs-EA composite was characterized by UV-Vis., FT-IR, powder XRD and HRTEM analyses. The average particle size of Cu NPs is found to be in the range of 20-25 nm as evident from HRTEM and copper content is estimated to be 3.18 wt%. EA acts both as a reducing agent as well as a stabilizer for the in situ formation of Cu NPs. A small portion of Cu NPs is also found to undergo aerobic oxidation to give Cu2O NPs which does not take part in the reactions. A series of arylboronic acids are converted to the corresponding phenols in high yields at short reaction time under milder reaction conditions. It is also observed that Cu NPs-EA composite can be reused at least four times with a significant decrease in the yield. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2014.09.016
• 作为产物：
  描述：

  3-氟吡啶 在 正丁基锂 、 二异丙胺 、 硼酸三异丙酯 、 sodium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 反应 0.75h， 以46%的产率得到3-氟吡啶-4-硼酸
  参考文献：
  名称：

  新型卤代吡啶基硼酸和酯的合成。第3部分：2或3-卤代吡啶-4-基硼酸和酯

  摘要：

  本文描述了用于合成和一般的方法的新的2-，或3-卤代吡啶-4-基硼酸和酯隔离12 - 14，18 - 20。考虑到使用n BuLi进行区域选择性的卤素金属交换或使用LDA进行定向原金属化并随后从适当的单或二卤代吡啶开始用三异丙基硼酸酯淬灭，制备这些化合物。迄今为止研究的所有底物均提供单一的区域异构硼酸或酯产物。另外，已经发现这些化合物与一系列的芳基卤化物进行了Pd催化的偶联，并授权了一种制备新吡啶库的策略。

  DOI：

  10.1016/s0040-4020(02)00416-7

文献信息

• CYCLIC ETHER PYRAZOL-4-YL-HETEROCYCLYL-CARBOXAMIDE COMPOUNDS AND METHODS OF USE
  申请人：Genentech, Inc.

  公开号：US20140088117A1

  公开（公告）日：2014-03-27

  Cyclic ether pyrazol-4-yl-heterocyclyl-carboxamide compounds of Formula I, including stereoisomers, geometric isomers, tautomers, and pharmaceutically acceptable salts thereof, wherein R 2 is a cyclic ether and X is thiazolyl, pyrazinyl, pyridinyl, or pyrimidinyl, are useful for inhibiting Pim kinase, and for treating disorders such as cancer mediated by Pim kinase. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

  公式I的环醚吡唑-4-基-杂环基-羧酰胺化合物，包括立体异构体、几何异构体、互变异构体和其药学上可接受的盐，其中R2为环醚，X为噻唑基、吡啶基、吡啶基或嘧啶基，可用于抑制Pim激酶，并用于治疗由Pim激酶介导的癌症等疾病。公开了使用公式I化合物进行体外、体内和体内诊断、预防或治疗哺乳动物细胞中的这类疾病或相关病理条件的方法。
• Phenoxypiperidines and analogs thereof useful as histamine H3 antagonists
  申请人：Mutahi W. Mwangi

  公开号：US20070167435A1

  公开（公告）日：2007-07-19

  Disclosed are compounds of the formula or a pharmaceutically acceptable salt or solvate thereof, wherein: M is CH or N; U and W are each CH, or one of U and W is CH and the other is N; X is a bond, alkylene, —C(O)—, —C(N—OR 5 )—, —C(N—OR 5 )—CH(R 6 )—, —CH(R 6 )—C(N—OR 5 )—, —O—, —OCH 2 —, —CH 2 O— or —S(O) 0-2 —; Y is —O—, —(CH 2 ) 2 —, —C(═O)—, —C(═NOR 7 )— or —SO 0-2 —; Z is a bond, optionally substituted alkylene or alkylene interrupted by a heteroatom or heterocyclic group; R 1 is optionally substituted alkyl, cycloalkyl, aryl, arylalkyl, heteroaryl, heterocycloalkyl, or benzimidazolyl or a derivative thereof; R 2 is optionally substituted alkyl, alkenyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl or heterocycloalkyl; and the remaining variables are as defined in the specification; compositions and methods for treating an allergy-induced airway response, congestion, diabetes, obesity, an obesity-related disorder, metabolic syndrome and a cognition deficit disorder using said compounds, alone or in combination with other agents.

  揭示了以下化合物的结构式或其药学上可接受的盐或溶剂，其中：M为CH或N；U和W分别为CH，或者U和W中的一个为CH，另一个为N；X为键，烷基，—C(O)—，—C(N—OR5)—，—C(N—OR5)—CH(R6)—，—CH(R6)—C(N—OR5)—，—O—，—OCH2—，—CH2O—或—S(O)0-2—；Y为—O—，—(CH2)2—，—C(═O)—，—C(═NOR7)—或—SO0-2—；Z为键，可选择地取代的烷基或被杂原子或杂环基中断的烷基；R1为可选择地取代的烷基，环烷基，芳基，芳基烷基，杂芳基，杂环烷基或苯并咪唑基或其衍生物；R2为可选择地取代的烷基，烯基，芳基，芳基烷基，杂芳基，杂芳基烷基，环烷基或杂环烷基；其余变量如规范中所定义；使用这些化合物，单独或与其他药剂联合使用，治疗由过敏引起的气道反应、充血、糖尿病、肥胖症、与肥胖有关的疾病、代谢综合征和认知缺陷障碍的组合物和方法。
• Trisubstituted Pyrimidines as Efficacious and Fast-Acting Antimalarials
  作者：Neil R. Norcross、Beatriz Baragaña、Caroline Wilson、Irene Hallyburton、Maria Osuna-Cabello、Suzanne Norval、Jennifer Riley、Laste Stojanovski、Frederick R. C. Simeons、Achim Porzelle、Raffaella Grimaldi、Sergio Wittlin、Sandra Duffy、Vicky M. Avery、Stephan Meister、Laura Sanz、Belén Jiménez-Díaz、Iñigo Angulo-Barturen、Santiago Ferrer、María Santos Martínez、Francisco Javier Gamo、Julie A. Frearson、David W. Gray、Alan H. Fairlamb、Elizabeth A. Winzeler、David Waterson、Simon F. Campbell、Paul Willis、Kevin D. Read、Ian H. Gilbert

  DOI：10.1021/acs.jmedchem.6b00028

  日期：2016.7.14

  dosed orally. Unfortunately, the compound is a potent inhibitor of cytochrome P450 enzymes, probably due to a 4-pyridyl substituent. Nevertheless, this is a lead molecule with a potentially useful antimalarial profile, which could either be further optimized or be used for target hunting.

  在本文中，我们描述了基于三取代嘧啶支架的恶性疟原虫表型命中的优化。这导致在疟疾的伯氏疟原虫小鼠模型中具有良好药代动力学和口服活性的化合物。在疟疾的伯氏疟原虫小鼠模型中，当每天口服30 mg / kg连续4天时，最有希望的化合物（13）表现出96％的寄生虫病降低。它也证明了在口服SCID小鼠模型中，ED90为11.7 mg / kg时，恶性疟原虫红细胞阶段的清除率较快。不幸的是，该化合物可能是4-吡啶基取代基，是细胞色素P450酶的有效抑制剂。然而，这是具有潜在有用的抗疟谱的先导分子，可以进一步优化或用于靶标狩猎。
• [EN] NOVEL SUBSTITUTED N-(3-FLUOROPROPYL)-PYRROLIDINE COMPOUNDS, PROCESSES FOR THEIR PREPARATION AND THERAPEUTIC USES THEREOF<br/>[FR] NOUVEAUX COMPOSÉS N-(3-FLUOROPROPYL)-PYRROLIDINE SUBSTITUÉS, LEURS PROCÉDÉS DE PRÉPARATION ET LEURS UTILISATIONS THÉRAPEUTIQUES
  申请人：SANOFI SA

  公开号：WO2018091153A1

  公开（公告）日：2018-05-24

  The present invention relates to novel substituted N-(3-fluoropropyl)-pyrrolidine compounds of formula (l-A): wherein R1 and R2 represent independently a hydrogen atom or a deuterium atom; A represents an oxygen or nitrogen atom; and SERM-F represents a selective estrogen receptor modulator fragment comprising an aryl or heteroaryl group linked to the adjacent "A" group. The invention also relates to the preparation and to the therapeutic uses of the compounds of formula (l-A) as inhibitors and degraders of estrogen receptors.

  本发明涉及新型的取代的N-(3-氟丙基)吡咯烷化合物，其化学式为(l-A)：其中R1和R2分别独立代表一个氢原子或一个氘原子；A代表一个氧原子或氮原子；SERM-F代表一个选择性雌激素受体调节剂片段，该片段包含与邻近的“A”基团相连的芳基或杂芳基。本发明还涉及化合物(l-A)的制备方法以及作为雌激素受体的抑制剂和降解剂的医疗用途。
• Discovery of Soticlestat, a Potent and Selective Inhibitor for Cholesterol 24-Hydroxylase (CH24H)
  作者：Tatsuki Koike、Masato Yoshikawa、Haruhi Kamisaki Ando、William Farnaby、Toshiya Nishi、Etsurou Watanabe、Jason Yano、Maki Miyamoto、Shigeru Kondo、Tsuyoshi Ishii、Takanobu Kuroita

  DOI：10.1021/acs.jmedchem.1c00864

  日期：2021.8.26

  to 24S-hydroxycholesterol (24HC). Despite a wide range of potential of CH24H as a drug target, no potent and selective inhibitors have been identified. Here, we report on the structure-based drug design (SBDD) of novel 4-arylpyridine derivatives based on the X-ray co-crystal structure of hit derivative 1b. Optimization of 4-arylpyridine derivatives led us to identify 3v ((4-benzyl-4-hydroxypiperidin-1-yl)(2

  胆固醇24-羟化酶（CH24H，CYP46A1）是一种大脑特异性细胞色素P450（CYP）家族酶，通过将胆固醇转化为24S-羟基胆固醇（24HC），在脑胆固醇稳态中发挥作用。尽管 CH24H 作为药物靶点具有广泛的潜力，但尚未发现有效的选择性抑制剂。在这里，我们报告了基于hit衍生物1b的X射线共晶结构的新型4-芳基吡啶衍生物的基于结构的药物设计（SBDD）。 4-芳基吡啶衍生物的优化使我们确定3v ((4-benzyl-4-羟基哌啶-1-基)(2,4'-联吡啶-3-基)甲酮，IC 50 = 7.4 nM) 是一种高效、选择性、脑渗透性 CH24H 抑制剂。小鼠口服3v后，大脑中 24HC 水平呈剂量依赖性降低（1、3 和 10 mg/kg）。化合物3v （soticlestat，也称为 TAK-935）目前正在临床研究中，作为治疗癫痫的新型药物类别，用于治疗 Dravet 综合征和 Lennox-Gastaut