6-溴-1,2,3,4-四氢喹喔啉 | 89980-70-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 6-溴-1,2,3,4-四氢喹喔啉
• 英文名称: 6-bromo-1,2,3,4-tetrahydroquinoxaline
• CAS: 89980-70-1
• 化学式: C₈H₉BrN₂
• 分子量: 213.077
• InChiKey: YWRDQVNEWKPADI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Bromo-1,2,3,4-tetrahydroquinoxaline
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-Bromo-1,2,3,4-tetrahydroquinoxaline
CAS number: 89980-70-1

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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: C8H9BrN2
Molecular weight: 213.1

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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 bromide.

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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-溴-1,2,3,4-四氢喹喔啉 在 氧气 、 C₄₀H₄₂Cu₂N₁₀⁽²⁺⁾*2F₆P^(1-) 作用下， 以 邻二氯苯 为溶剂， 以68 %的产率得到6-溴喹喔啉
  参考文献：
  名称：

  Cu(I)配合物催化N-杂环脱氢

  摘要：

  开发了一种用于各种含氮杂环脱氢以提供喹啉和吲哚的铜催化方法。使用 2 mol% 的铜配合物Cat 3作为催化剂并使用 O 2作为氧化剂，在 1,2-二氯苯中于 120 °C 下对一系列 1,2,3,4-四氢喹啉进行脱氢，得到所需的喹啉。该方法以10 mol%的TEMPO为添加剂，O 2为氧化剂，在2 mol%的铜络合物Cat 2存在下，在室温下四氢呋喃中对多种二氢吲哚进行脱氢，高收率地得到吲哚。机理研究表明，脱氢活性归因于铜(I)配合物被O 2氧化形成铜(II)活性物质，这一点已被高分辨率质谱(HRMS)证实。电子顺磁共振（EPR）光谱法证明，铜催化的脱氢反应通过超氧自由基阴离子（·O 2 - ）进行。原位红外光谱表明二氢喹啉中间体是在1,2,3,4-四氢喹啉脱氢过程中形成的。

  DOI：

  10.1021/acs.joc.3c02768
• 作为产物：
  描述：

  6-溴喹喔啉 在 ammonia borane 、 [Co(2,2':6',2''-terpyridine)Br₂] 作用下， 以 甲醇 为溶剂， 以86 %的产率得到6-溴-1,2,3,4-四氢喹喔啉
  参考文献：
  名称：

  Co(II) 催化 N-杂芳烃室温无添加剂转移氢化

  摘要：

  传统的催化剂开发依赖于配体和预催化剂的多步合成和分离。设计一种可以用易于获得的起始材料原位组装的催化系统可以降低反应复杂性并提高合成效用。在此，我们报道了一种廉价且市售的CoBr 2 ·H 2 O/三联吡啶催化的有效且直接的N-杂芳烃转移氢化(TH)方案，在环境条件下利用NH 3 ·BH 3 (AB)。多种底物和生物活性分子的合成证明了其实际适用性。对照实验和 DFT 研究阐明了其机制。

  DOI：

  10.1021/acs.orglett.4c02090

文献信息

• [EN] BENZOPIPERAZINE COMPOSITIONS AS BET BROMODOMAIN INHIBITORS<br/>[FR] COMPOSITIONS DE BENZOPIPÉRAZINE EN TANT QU'INHIBITEURS DE BROMODOMAINES BET
  申请人：BAIR KENNETH W

  公开号：WO2015074081A1

  公开（公告）日：2015-05-21

  The present invention relates to inhibitors of bromo and extra terminal (BET) bromodomains that are useful for the treatment of cancer, inflammatory diseases, diabetes, and obesity, having Formula (I): wherein X, Y, Z, R1, R2, R4 and R7 are defined herein.

  本发明涉及用于治疗癌症、炎症性疾病、糖尿病和肥胖的溴和末端（BET）溴结构域抑制剂，具有公式（I）：其中X、Y、Z、R1、R2、R4和R7的定义如下。
• Acceptorless Dehydrogenation of <i>N</i>-Heterocycles and Secondary Alcohols by Ru(II)-NNC Complexes Bearing a Pyrazoyl-indolyl-pyridine Ligand
  作者：Qingfu Wang、Huining Chai、Zhengkun Yu

  DOI：10.1021/acs.organomet.7b00902

  日期：2018.2.26

  Ruthenium(II) hydride complexes bearing a pyrazolyl-(2-indol-1-yl)-pyridine ligand were synthesized and structurally characterized by NMR analysis and X-ray single crystal crystallographic determinations. These complexes efficiently catalyzed acceptorless dehydrogenation of N-heterocycles and secondary alcohols, respectively, exhibiting highly catalytic activity with a broad substrate scope. The present

  合成了带有吡唑基-（2-吲哚-1-基）-吡啶配体的氢化钌（II）配合物，并通过NMR分析和X射线单晶晶体学测定对其结构进行了表征。这些配合物分别有效地催化了N-杂环和仲醇的无受体脱氢，表现出高催化活性，具有广泛的底物范围。本工作已经建立了构造高活性过渡金属配合物催化剂的策略，并为合成芳族N-杂环化合物和酮提供了原子经济和环境友好的方案。
• Water-involving transfer hydrogenation and dehydrogenation of N-heterocycles over a bifunctional MoNi4 electrode
  作者：Mengyang Li、Cuibo Liu、Yi Huang、Shuyan Han、Bin Zhang

  DOI：10.1016/s1872-2067(21)63834-2

  日期：2021.11

  A room-temperature electrochemical strategy for hydrogenation (deuteration) and reverse dehydrogenation of N-heterocycles over a bifunctional MoNi4 electrode is developed, which includes the hydrogenation of quinoxaline using H2O as the hydrogen source with 80% Faradaic efficiency and the reverse dehydrogenation of hydrogen-rich 1,2,3,4-tetrahydroquinoxaline with up to 99% yield and selectivity. The

  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。
• MOF-Derived Subnanometer Cobalt Catalyst for Selective C–H Oxidative Sulfonylation of Tetrahydroquinoxalines with Sodium Sulfinates
  作者：Feng Xie、Guang-Peng Lu、Rong Xie、Qing-Hua Chen、Huan-Feng Jiang、Min Zhang

  DOI：10.1021/acscatal.9b00037

  日期：2019.4.5

  The development and utilization of reusable base-metal catalysts is a central topic in catalysis. Herein, via a catalyst design strategy, we present the preparation of a highly dispersed and acid-resistant subnanometer cobalt catalyst (<1 nm) by a MOF-templated method, which has been utilized for selective C–H oxidative sulfonylation of tetrahydroquinoxalines with odorless sodium sulfinates. The transformation

  可重复使用的贱金属催化剂的开发和利用是催化的中心课题。在此，通过催化剂设计策略，我们介绍了通过MOF模板方法制备高度分散且耐酸的亚纳米钴催化剂（<1 nm）的方法，该催化剂已用于四氢喹喔啉的选择性C–H氧化磺酰化，且无味。亚硫酸钠。该转化使得能够产生具有良好的底物和官能团相容性，高的区域选择性和化学选择性以及使用天然丰富且可重复使用的金属催化剂的优点的各种磺酰基喹喔啉。提出的工作为进一步设计多相纳米催化剂和制造难以通过均相催化制备或难以获得的功能产品提供了潜力。
• 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。