6-氟喹喔啉 | 1644-14-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 6-氟喹喔啉
• 中文别名: 6-氟喹噁啉
• 英文名称: 6-fluoroquinoxaline
• CAS: 1644-14-0
• 化学式: C₈H₅FN₂
• mdl: MFCD03094247
• 分子量: 148.14
• InChiKey: JIXCXZJOGOGGIU-UHFFFAOYSA-N

物化性质

• 熔点：
  33-35 °C
• 沸点：
  241.9±20.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 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: 6-Fluoroquinoxaline
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: 6-Fluoroquinoxaline
CAS number: 1644-14-0

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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.
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: C8H5FN2
Molecular weight: 148.1

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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：

  6-氟喹喔啉 在 重水 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以88%的产率得到C₈H₅⁽²⁾H₄FN₂
  参考文献：
  名称：

  双功能MoNi4电极上N-杂环的涉及水的转移氢化和脱氢

  摘要：

  开发了一种在双功能 MoNi 4电极上对N-杂环进行加氢（氘化）和反向脱氢的室温电化学策略，其中包括使用 H 2 O 作为氢源的喹喔啉加氢（法拉第效率为 80%）和反向脱氢富氢 1,2,3,4-四氢喹喔啉的产率和选择性高达 99%。该原位生成的活性氢原子（H *）的振振有词涉及喹喔啉，其中提出了一种连续氢自由基偶联的电子传递路径的氢化。值得注意的是，MoNi 4合金在仅 50 mV 的过电位下表现出有效的喹喔啉氢化，因为它具有在碱性介质中提供 H* 的优异水离解能力。原位拉曼测试表明，Ni II / Ni III氧化还原对可以促进脱氢过程，是低值析氧的有前途的阳极替代品。令人印象深刻的是，使用 D 2 O可以轻松实现高达 99% 的氘化率的电催化氘化。该方法能够生产一系列功能化的氢化和氘化喹喔啉。

  DOI：

  10.1016/s1872-2067(21)63834-2
• 作为产物：
  描述：

  4-氟-2-硝基苯胺 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 6-氟喹喔啉
  参考文献：
  名称：

  Preparation of 6-Substituted Quinoxaline JSP-1 Inhibitors by Microwave Accelerated Nucleophilic Substitution

  摘要：

  已通过在计算机控制的微波辐射下，将6-fluoroquinoxaline与胺类和含氮杂环化合物进行亲核取代，制备了一小型6-氨基喹喔啉库。某些化合物在体外生物测定中被发现是JNK刺激酶-1 (JSP-1) 的强力抑制剂。

  DOI：

  10.3390/11120988

文献信息

• Derisking the Cu-Mediated ¹⁸F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands
  作者：Nicholas J. Taylor、Enrico Emer、Sean Preshlock、Michael Schedler、Matthew Tredwell、Stefan Verhoog、Joel Mercier、Christophe Genicot、Véronique Gouverneur

  DOI：10.1021/jacs.7b03131

  日期：2017.6.21

  Molecules labeled with fluorine-18 (18F) are used in positron emission tomography to visualize, characterize and measure biological processes in the body. Despite recent advances in the incorporation of 18F onto arenes, the development of general and efficient approaches to label radioligands necessary for drug discovery programs remains a significant task. This full account describes a derisking approach

  用氟 18 (18F) 标记的分子用于正电子发射断层扫描，以可视化、表征和测量体内的生物过程。尽管最近在将 18F 掺入芳烃方面取得了进展，但开发通用且有效的方法来标记药物发现计划所需的放射性配体仍然是一项重大任务。这个完整的描述描述了杂环正电子发射断层扫描 (PET) 放射性配体的放射合成方法，使用铜介导的 18F 氟化芳基硼试剂与 18F 氟化物作为模型反应。该方法基于一项研究，该研究检查了药物开发中常用的杂环的存在如何影响代表性芳基硼试剂的 18F-氟化效率，以及超过 50 种（杂）芳基硼酸酯的标记。这组数据允许将这种去风险策略应用于七种结构复杂的药物相关含杂环分子的成功放射合成。
• Aqueous Hydrofluoric Acid Catalyzed Facile Synthesis of 2,3,6-Substituted Quinoxalines
  作者：A. Chandra Shekhar、A. Ravi Kumar、G. Sathaiah、K. Raju、P. V. S. S. Srinivas、P. Shanthan Rao、B. Narsaiah

  DOI：10.1002/jhet.1753

  日期：2014.9

  A versatile synthetic route for the preparation of 2,3,6‐trisubstituted quinoxalines in excellent yield is developed from θ‐diamines and 1,2‐dicarbonyl compounds in which aqueous hydrofluoric acid was employed as the medium and catalyst. Other salient features of this protocol include milder conditions, absence of coupling agents, and easy workup procedures.

  从θ-二胺和1,2-二羰基化合物（使用含水氢氟酸作为介质和催化剂）开发出了一种通用的合成路线，该路线以优异的产率制备2,3,6-三取代的喹喔啉。该协议的其他显着特征包括条件较温和，不存在偶联剂以及易于处理的程序。
• Versatile (Pentamethylcyclopentadienyl)rhodium-2,2′-Bipyridine (Cp*Rh-bpy) Catalyst for Transfer Hydrogenation of N-Heterocycles in Water
  作者：Lingjuan Zhang、Ruiying Qiu、Xiao Xue、Yixiao Pan、Conghui Xu、Huanrong Li、Lijin Xu

  DOI：10.1002/adsc.201500491

  日期：2015.11.16

  An investigation employing the catalytic system consisting of (pentamethylcyclopentadienyl)rhodium dichloride dimer [Cp*RhCl2]2 and 2,2′-bipyridine (bpy) for transfer hydrogenation of a variety of quinoxalines, quinoxalinones, quinolines and indoles under aqueous conditions with formate as the hydrogen source is reported. This approach provides various tetrahydroquinoxalines, dihydroquinoxalinones

  采用由（五甲基环戊二烯基）二氯化铑二聚体[Cp * RhCl 2 ] 2组成的催化体系的研究报道了在水溶液中以甲酸为氢源，将2,2'-联吡啶（bpy）用于转移各种喹喔啉，喹喔啉酮，喹啉和吲哚的氢化反应。该方法以良好或优异的产率提供了各种四氢喹喔啉，二氢喹喔啉，四氢喹啉和二氢吲哚。催化剂对喹喔啉和喹喔啉酮的活性极好，底物与催化剂之比（S / C）为10000是可行的。配体的选择对于催化至关重要，并且水相还原显示出高度的pH依赖性，而酸性pH值则需要最佳还原。催化剂易于获得，并且反应在不需要惰性气氛的情况下操作简单。
• Tetrabutylammonium Bromide-Catalyzed Transfer Hydrogenation of Quinoxaline with HBpin as a Hydrogen Source
  作者：Qi Guo、Jingchao Chen、Guoli Shen、Guangfu Lu、Xuemei Yang、Yan Tang、Yuanbin Zhu、Shiyuan Wu、Baomin Fan

  DOI：10.1021/acs.joc.1c02537

  日期：2022.1.7

  A metal-free environmentally benign, simple, and efficient transfer hydrogenation process of quinoxaline has been developed using the HBpin reagent as a hydrogen source. This reaction is compatible with a variety of quinoxalines offering the desired tetrahydroquinoxalines in moderate-to-excellent yields with Bu4NBr as a noncorrosive and low-cost catalyst.

  以HBpin试剂为氢源，开发了一种环境友好、简单、高效的喹喔啉转移加氢工艺。该反应与多种喹喔啉相容，以中等至优异的收率提供所需的四氢喹喔啉，Bu 4 NBr 作为非腐蚀性和低成本的催化剂。
• Rhodium-catalyzed transfer hydrogenation of quinoxalines with water as a hydrogen source
  作者：Xia Zhang、Jingchao Chen、Ruhima Khan、Guoli Shen、Zhenxiu He、Yongyun Zhou、Baomin Fan

  DOI：10.1039/c9ob02095k

  日期：——

  Rhodium-catalyzed transfer hydrogenation of quinoxalines with water as a hydrogen source was reported. The reaction allowed the simple preparation of tetrahydroquinoxalines under mild conditions. The deuterium-labelling experiment confirmed that water is the sole hydrogen source in the transfer hydrogenation reaction.

  据报道铑以水为氢源催化喹喔啉的转移加氢。该反应允许在温和的条件下简单地制备四氢喹喔啉。氘标记实验证实水是转移氢化反应中唯一的氢源。