3-硝基-2-(1-吡咯烷基)吡啶 | 26820-73-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 3-硝基-2-(1-吡咯烷基)吡啶
• 英文名称: 3-nitro-2-(pyrrolidin-1-yl)pyridine
• 英文别名: 3-Nitro-2-(1-pyrrolidinyl)pyridine；3-nitro-2-pyrrolidin-1-ylpyridine
• CAS: 26820-73-5
• 化学式: C₉H₁₁N₃O₂
• mdl: MFCD03001300
• 分子量: 193.205
• InChiKey: SMRXLVBZPIVHDZ-UHFFFAOYSA-N

物化性质

• 熔点：
  42 °C
• 沸点：
  102°C 0,3mm
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  62
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Nitro-2-(pyrrolidin-1-yl)pyridine
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-Nitro-2-(pyrrolidin-1-yl)pyridine
CAS number: 26820-73-5

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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: C9H11N3O2
Molecular weight: 193.2

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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.

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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-硝基-2-(1-吡咯烷基)吡啶 在 铁粉 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 生成 2-(pyrrolidin-1-yl)pyridin-3-amine
  参考文献：
  名称：

  叔氨基效应促进异硫氰酸芳基酯的重排：苯并咪唑并硫氮杂ze和苯并咪唑硫代醚的通用方法。

  摘要：

  已经开发了通过由叔氨基效应促进的芳基异硫氰酸酯的分子内亲核加成/环扩展重排来制备苯并咪唑并噻唑啉酮和苯并咪唑硫醚衍生物的通用方法。该反应由低成本樟脑磺酸催化，可耐受广泛的底物范围，并具有完全的原子经济性。通过简单的操作就可以容易地获得结构上令人着迷的苯并咪唑并硫氮杂pine和苯并咪唑硫醚产物（高达98％）。

  DOI：

  10.1021/acs.joc.0c01806
• 作为产物：
  描述：

  2-氯-3-硝基吡啶 在 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 28.08h， 生成 3-硝基-2-(1-吡咯烷基)吡啶
  参考文献：
  名称：

  2,2,2-三氟乙氧基芳族杂环：杂芳基氯化物的水解稳定替代品

  摘要：

  在本文中，我们描述了2,2,2-三氟乙氧基作为水解不稳定的杂芳基氯化物的替代离去基团。该组在保持S N Ar反应中对亲核试剂的反应性的同时，提供了提高的货架稳定性。高亮度显示的三氟乙基醚被证明是耐受含水Suzuki条件，从而允许连续的铃木/ S Ñ的Ar处理难以接近杂环氯化物。三氟乙基醚的策略性使用可以储存原本不稳定的杂环氯化物，并限制了昂贵的分解过程。

  DOI：

  10.1021/acs.joc.8b02453

文献信息

• A palladium nanoparticle-catalyzed aryl–amine coupling reaction: high performance of aryl and pyridyl chlorides as the coupling partner
  作者：Debkumar Nandi、Rafique Ul Islam、Nishu Devi、Samarjeet Siwal、Kaushik Mallick

  DOI：10.1039/c7nj03447d

  日期：——

  Carbon nitride (CN)-supported nanosized palladium particles, Pd–CN, have been found to be an active catalyst system for the amination of aryl and pyridyl chloride moieties in the presence of dialkyl amine under mild reaction conditions. The recyclability study of the reaction shows the stable performance of the catalyst without a significant loss of catalytic activity for a couple of cycles.

  已经发现，在温和的反应条件下，在二烷基胺存在下，氮化碳（CN）负载的纳米钯颗粒Pd-CN是一种用于芳基和吡啶氯部分胺化的活性催化剂体系。反应的可循环性研究表明，在几个循环中，催化剂的性能稳定，而催化活性没有明显损失。
• Room-Temperature Amination of Chloroheteroarenes in Water by a Recyclable Copper(II)-Phosphaadamantanium Sulfonate System
  作者：Udaysinh Parmar、Dipesh Somvanshi、Santosh Kori、Aman A. Desai、Rambabu Dandela、Dilip K. Maity、Anant R. Kapdi

  DOI：10.1021/acs.joc.1c00845

  日期：2021.7.2

  Buchwald–Hartwig amination of chloroheteroarenes has been a challenging synthetic process, with very few protocols promoting this important transformation at ambient temperature. The current report discusses about an efficient copper-based catalytic system (Cu/PTABS) for the amination of chloroheteroarenes at ambient temperature in water as the sole reaction solvent, a combination that is first to

  氯杂芳烃的 Buchwald-Hartwig 胺化一直是一个具有挑战性的合成过程，很少有方案在环境温度下促进这种重要的转化。目前的报告讨论了一种高效的铜基催化系统 (Cu/PTABS)，用于在环境温度下在作为唯一反应溶剂的水中胺化氯杂芳烃，这是首次报道的组合。多种氯杂芳烃可以在温和的反应条件下与伯胺和仲胺以及选定的氨基酸酯有效偶联。所开发协议的催化效率还促进了抗生素（氟沙星）和抗癌药物等活性药物成分 (API) 的后期功能化。催化系统在 0 的极低浓度下也能高效运行。0001 mol % (TON = 980,000) 并且可以循环使用 12 次而没有任何明显的活性损失。理论计算表明，配体 PTABS 的 π 受体能力是催化体系显着高反应性的主要原因。使用 UV-VIS 和 ESR 光谱对反应中的催化物质进行了初步表征，为 Cu(II) 氧化态提供了证据。
• Three-component reaction between amines, carbon disulfide and electron-deficient derivatives of chloropyridine or chlorobenzene: synthesis of 3,6-diazaspiro[4.5]deca-2,7,9-trien-6-ium chloride and dithioylcarbamates derivatives
  作者：Reza Ranjbar-Karimi、Aliyeh Khajeh-Khezri、Mohammad Anary-Abbasinejad

  DOI：10.1007/s13738-013-0300-y

  日期：2014.4

  In this study, three-component reaction of some primary and secondary amines with carbon disulfide in the presence of electron-deficient derivatives of chloropyridine or chlorobenzene in the CH3CN as a solvent is reported. The reaction of primary amines with carbon disulfide and electron-deficient compounds of chloropyridine or chlorobenzene after 6–8 h afforded the three-component addition product. The reaction of secondary amines with carbon disulfide and electron-deficient compounds of chloropyridine or chlorobenzene after 3–4 h afforded the two-component addition product. The product(s) of reactions were purified by recrystallization or column chromatography and their structures were identified by spectroscopy techniques such as 1H-NMR, 13C-NMR, IR, UV and elemental analysis. The reactions were carried out under mild conditions and without using a catalyst.

  在这项研究中，报道了在氯吡啶或氯苯的缺电子衍生物存在下，在CH3CN作为溶剂中，一些伯胺和仲胺与二硫化碳的三组分反应。伯胺与二硫化碳以及氯吡啶或氯苯的缺电子化合物反应 6-8 小时后得到三组分加成产物。仲胺与二硫化碳以及氯吡啶或氯苯的缺电子化合物反应 3-4 小时后得到双组分加成产物。反应产物通过重结晶或柱色谱纯化，并通过1H-NMR、13C-NMR、IR、UV和元素分析等光谱技术鉴定其结构。反应在温和条件下进行且不使用催化剂。
• The Effects of Ring Substituents and Leaving Groups on the Kinetics of SNAr Reactions of 1-Halogeno- and 1-Phenoxy-nitrobenzenes with Aliphatic Amines in Acetonitrile
  作者：Michael R. Crampton、Thomas A. Emokpae、Chukwuemeka Isanbor

  DOI：10.1002/ejoc.200600968

  日期：2007.3

  attack although this may be mediated by reduced steric congestion around the reaction centre. Specific steric effects, leading to rate-retardation, is noted for the ortho-CF3 group. The 1-phenoxy compounds are subject to base catalysis and values of kAm/k–1 are reduced relative to more strongly activated compounds. This is likely to reflect increases in values of k–1 coupled with decreases in values of

  报告了一系列 1-氯-、1-氟-和 1-苯氧基-硝基苯的反应速率常数，这些苯由 CF3 或 CN 基团或环氮与正丁胺、吡咯烷或哌啶在乙腈中活化。将结果与先前报告的更强环活化化合物的结果进行比较。环活化的减少导致亲核攻击的 k1 值降低，尽管这可能是通过减少反应中心周围的空间拥挤来介导的。注意到邻位 组的特定空间效应导致速率延迟。1-苯氧基化合物受碱催化作用，相对于活性更强的化合物，kAm/k–1 值降低。这可能反映了 k-1 值的增加以及 kAm 值的降低，因为从两性离子中间体到催化胺的质子转移在热力学上变得不太有利。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Nucleophilic heteroaromatic substitution: Kinetics of the reactions of nitropyridines with aliphatic amines in dipolar aprotic solvents
  作者：Chukwuemeka Isanbor、Thomas A. Emokpae

  DOI：10.1002/kin.20297

  日期：2008.3

  reported for the reactions of 2-chloro-5-nitropyridine 2a, 2-chloro-3-nitropyridine 2b, and the corresponding 2-phenoxy derivatives 2c with n-butylamine, pyrrolidine and piperidine and 2d with n-butylamine and pyrrolidine in dimethyl sulfoxide (DMSO) as solvent. The same reactions in acetonitrile had been reported earlier (Crampton et al., Eur J Org Chem 2007, 1378–1383). Values in these solvents are compared

  报告了 2-氯-5-硝基吡啶 2a、2-氯-3-硝基吡啶 2b 和相应的 2-苯氧基衍生物 2c 与正丁胺、吡咯烷和哌啶以及 2d 与正丁胺和吡咯烷的反应速率数据以二甲亚砜 (DMSO) 为溶剂。早先已经报道了乙腈中的相同反应（Crampton 等人，Eur J Org Chem 2007，1378–1383）。这些溶剂中的值与 2,4-二硝基氯苯 3a、2,6-二硝基氯苯 3b 和相应的硝基活化二苯醚 3c 和 3d 的值进行比较。在两种溶剂中与正丁胺的反应给出了 kobs 值，该值随胺浓度线性增加，表明亲核攻击是速率限制的。唯一的例外是观察到碱催化的乙腈与 2c 的反应。k1 的值，亲核攻击的速率常数，按吡咯烷 > 哌啶 > 正丁胺的顺序递减。在乙腈中，动力学数据显示 k/k 比值大于 1，而在 DMSO 中则相反。对于苯氧基衍生物，取代是观察到的唯一过程。在 1-苯氧基衍生物的反应中