2-苄基氨基-6-溴吡啶 | 427900-17-2

• 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: 2-苄基氨基-6-溴吡啶
• 英文名称: 2-N-benzylamino-6-bromopyridine
• 英文别名: N-benzyl-6-bromopyridin-2-amine；2-benzylamino-6-bromopyridine
• CAS: 427900-17-2
• 化学式: C₁₂H₁₁BrN₂
• 分子量: 263.137
• InChiKey: VCWLITVACKPQRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Benzylamino-6-bromopyridine
Synonyms: N-Benzyl-6-bromopyridin-2-amine

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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: 2-Benzylamino-6-bromopyridine
CAS number: 427900-17-2

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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: C12H11BrN2
Molecular weight: 263.1

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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：

  2-苄基氨基-6-溴吡啶 在 18-冠醚-6 tris(dibenzylideneacetone)dipalladium (0) 、 potassium tert-butylate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 苯 为溶剂， 反应 12.0h， 生成 bis{6-[6'-((benzylamino)pyrid-2'-yl)amino]pyrid-2-yl}amine
  参考文献：
  名称：

  Self-Complementarity of Oligo-2-aminopyridines:  A New Class of Hydrogen-Bonded Ladders

  摘要：

  A new class of hydrogen-bonded ladders based on hydrogen-bonded dimerization of oligo-alpha-aminopryidines has been demonstrated. Jorgensen's model can be successfully applied to this hydrogen-bonding system in nonpolar solvents. The results show the competitive enthalpy/entropy compensation relationship upon dimerization, Although increasing the number of hydrogen-bonding interactions would enhance the hydrogen-bonding stabilization enthalpy, this stabilization enthalpy per unit would be partially sacrificed to compensate for the entropy loss due to dimerization. These results clearly support the importance of preorganization in designing hydrogen-bonding guest-host molecules.

  DOI：

  10.1021/ja011679p
• 作为产物：
  描述：

  2,6-二溴吡啶 、 苄胺 反应 0.5h， 以100%的产率得到2-苄基氨基-6-溴吡啶
  参考文献：
  名称：

  VX-509（Decernotinib）的发现：一种有效的选择性Janus Kinase 3抑制剂，用于治疗自身免疫性疾病

  摘要：

  尽管存在几种治疗选择，但是仍然需要针对多种自身免疫疾病的更有效，安全和方便的治疗方法。靶向Janus酪氨酸激酶（JAKs）在细胞信号传导反应中起着重要作用，并且可以促进与疾病相关的异常免疫功能，它已成为开发新型自身免疫性疾病疗法的一种新颖且有吸引力的方法。我们针对免疫细胞中的关键信号激酶JAK3筛选了我们的化合物文库，并鉴定了多个支架对该支架表现出良好的抑制活性。选择了特定的目标支架1 H-吡咯并[2,3- b ]吡啶系列（7-氮杂吲哚），部分基于结合亲和力（K i）以及细胞效能的基础上。该化学系列的优化导致鉴定出一种新型，有效和选择性的JAK3抑制剂VX-509（地加罗非尼），与大鼠移植模型（HvG）相比，它在大鼠宿主体内显示出良好的疗效。基于这些发现，看来VX-509为治疗多种自身免疫性疾病提供了潜力。

  DOI：

  10.1021/acs.jmedchem.5b00301

文献信息

• Iron/Amino Acid Catalyzed Direct N-Alkylation of Amines with Alcohols
  作者：Yingsheng Zhao、Siong Wan Foo、Susumu Saito

  DOI：10.1002/anie.201006660

  日期：2011.3.21

  Ironing it out: The straightforward N‐alkylation using alcohols and iron/amino acid catalysis is described (see scheme). The reaction does not proceed by the conventional “borrowing hydrogen” mechanism, but appears to involve a substitution pathway (SN) at the sp3 carbon atom bearing the hydroxy group of the alcohol. Developing a catalyst that is effective at a near neutral pH was key to the successful

  解决：描述了使用醇和铁/氨基酸催化的简单N-烷基化反应（参见方案）。该反应不是通过常规的“借入氢”机理进行的，而是似乎在带有醇羟基的sp 3碳原子上涉及一个取代途径（S N）。开发一种在接近中性pH值时有效的催化剂是成功进行N烷基化的关键。
• Rational Optimization of Lewis-Acid Catalysts for Direct Alcohol Amination, Part 2 - Titanium Triflimide as New Active Catalyst
  作者：Pierre-Adrien Payard、Céline Finidori、Laurélia Guichard、Damien Cartigny、Matthieu Corbet、Lhoussain Khrouz、Laurent Bonneviot、Raphael Wischert、Laurence Grimaud、Marc Pera-Titus

  DOI：10.1002/ejoc.202000413

  日期：2020.6.16

  reactivity of a new, previously undescribed (see part I), titanium triflimide catalyst was further investigated for the direct amination of alcohols. Addition of pyridine‐based ligands allows to increase the activity. The scope of the reaction has been significantly increased compared to other Lewis‐acid‐based protocols. Finally, some mechanistic insights based on EPR spectroscopy and DFT are provided.

  进一步研究了一种新的，以前未描述的（见第一部分）三氟化钛催化剂的反应性，用于直接胺化醇。添加吡啶基配体可以增加活性。与其他基于路易斯酸的方案相比，该反应的范围已大大增加。最后，提供了一些基于EPR光谱和DFT的力学见解。
• Synthesis, Structure, and Fullerene-Complexing Property of Azacalix[6]aromatics
  作者：Shi-Xin Fa、Li-Xia Wang、De-Xian Wang、Liang Zhao、Mei-Xiang Wang

  DOI：10.1021/jo5003714

  日期：2014.4.18

  Synthesis, structure, and fullerene-binding property of azacalix[6]aromatics were systematically studied. By means of [3 + 3] and [2 + 2 + 2] fragment coupling protocols, a number of azacalix[6]aromatics containing different combinations of benzene, pyridine, and pyrimidine rings and various substituents on the bridging nitrogen atoms were synthesized conveniently in moderate to good yields. The resulting

  系统研究了氮杂杯[6]芳烃的合成，结构和富勒烯结合性能。通过[3 + 3]和[2 + 2 + 2]片段偶联方案，可以方便地合成许多含有苯，吡啶和嘧啶环的不同组合以及桥接氮原子上各种取代基的氮杂杯[6]芳族化合物中等至良好的产量。生成的大环化合物根据芳香族结构单元采用固态对称且畸变严重的1,3,5-交替构象，而在溶液中，它们以相对于NMR时间尺度快速互换的构象异构体的混合物形式存在。所有大环化合物都能与C 60和C 70形成1：1的配合物在甲苯中的缔合常数最高为7.28×10 4 M –1。在结晶状态下，氮杂杯[6]芳烃与C 60和C 70形成配合物，客体和客体之间的化学计量比为2：1、1：1和1：2。Azacalix [6]芳烃主要通过形成夹心结构与富勒烯相互作用，其中C 60或C 70被两个大环夹在中间。X射线分子结构显示，凹的azacalix [6]芳烃与凸的富勒烯C 60和C 70之
• Discovery of VX-509 (Decernotinib): A Potent and Selective Janus Kinase 3 Inhibitor for the Treatment of Autoimmune Diseases
  作者：Luc J. Farmer、Mark W. Ledeboer、Thomas Hoock、Michael J. Arnost、Randy S. Bethiel、Youssef L. Bennani、James J. Black、Christopher L. Brummel、Ananthsrinivas Chakilam、Warren A. Dorsch、Bin Fan、John E. Cochran、Summer Halas、Edmund M. Harrington、James K. Hogan、David Howe、Hui Huang、Dylan H. Jacobs、Leena M. Laitinen、Shengkai Liao、Sudipta Mahajan、Valerie Marone、Gabriel Martinez-Botella、Pamela McCarthy、David Messersmith、Mark Namchuk、Luke Oh、Marina S. Penney、Albert C. Pierce、Scott A. Raybuck、Arthur Rugg、Francesco G. Salituro、Kumkum Saxena、Dean Shannon、Dina Shlyakter、Lora Swenson、Shi-Kai Tian、Christopher Town、Jian Wang、Tiansheng Wang、M. Woods Wannamaker、Raymond J. Winquist、Harmon J. Zuccola

  DOI：10.1021/acs.jmedchem.5b00301

  日期：2015.9.24

  signaling kinase in immune cells, and identified multiple scaffolds showing good inhibitory activity for this kinase. A particular scaffold of interest, the 1H-pyrrolo[2,3-b]pyridine series (7-azaindoles), was selected for further optimization in part on the basis of binding affinity (Ki) as well as on the basis of cellular potency. Optimization of this chemical series led to the identification of VX-509

  尽管存在几种治疗选择，但是仍然需要针对多种自身免疫疾病的更有效，安全和方便的治疗方法。靶向Janus酪氨酸激酶（JAKs）在细胞信号传导反应中起着重要作用，并且可以促进与疾病相关的异常免疫功能，它已成为开发新型自身免疫性疾病疗法的一种新颖且有吸引力的方法。我们针对免疫细胞中的关键信号激酶JAK3筛选了我们的化合物文库，并鉴定了多个支架对该支架表现出良好的抑制活性。选择了特定的目标支架1 H-吡咯并[2,3- b ]吡啶系列（7-氮杂吲哚），部分基于结合亲和力（K i）以及细胞效能的基础上。该化学系列的优化导致鉴定出一种新型，有效和选择性的JAK3抑制剂VX-509（地加罗非尼），与大鼠移植模型（HvG）相比，它在大鼠宿主体内显示出良好的疗效。基于这些发现，看来VX-509为治疗多种自身免疫性疾病提供了潜力。
• Self-Complementarity of Oligo-2-aminopyridines:  A New Class of Hydrogen-Bonded Ladders
  作者：Man-kit Leung、Ashis B. Mandal、Chih-Chieh Wang、Gene-Hsiang Lee、Shie-Ming Peng、Hsing-Ling Cheng、Guor-Rong Her、Ito Chao、Hsiu-Feng Lu、Ying-Chieh Sun、Mei-Ying Shiao、Pi-Tai Chou

  DOI：10.1021/ja011679p

  日期：2002.4.1

  A new class of hydrogen-bonded ladders based on hydrogen-bonded dimerization of oligo-alpha-aminopryidines has been demonstrated. Jorgensen's model can be successfully applied to this hydrogen-bonding system in nonpolar solvents. The results show the competitive enthalpy/entropy compensation relationship upon dimerization, Although increasing the number of hydrogen-bonding interactions would enhance the hydrogen-bonding stabilization enthalpy, this stabilization enthalpy per unit would be partially sacrificed to compensate for the entropy loss due to dimerization. These results clearly support the importance of preorganization in designing hydrogen-bonding guest-host molecules.