2-(4-硝基苯基)咪唑并[1,2-a]吡啶 | 3323-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(4-硝基苯基)咪唑并[1,2-a]吡啶
• 中文别名: 2-(4-硝基苯基)咪唑并[1,2-A]吡啶
• 英文名称: 2-(4-nitrophenyl)imidazo[1,2-a]pyridine
• 英文别名: 2-<4-Nitro-phenyl>-imidazo<1,2-a>pyridin
• CAS: 3323-26-0
• 化学式: C₁₃H₉N₃O₂
• mdl: MFCD00276341
• 分子量: 239.233
• InChiKey: SNBCSKCONKUZBA-UHFFFAOYSA-N

物化性质

• 熔点：
  263-264 °C
• 密度：
  1.34±0.1 g/cm3(Predicted)
• 溶解度：
  1.7 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.1
• 氢给体数：
  0
• 氢受体数：
  3

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: 2-(4-Nitrophenyl)imidazo[1,2-a]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: 2-(4-Nitrophenyl)imidazo[1,2-a]pyridine
CAS number: 3323-26-0

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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: C13H9N3O2
Molecular weight: 239.2

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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：

  2-(4-硝基苯基)咪唑并[1,2-a]吡啶 在 盐酸 、 水 、 tin(ll) chloride 作用下， 生成 N-acetyl-sulfanilic acid-(4-imidazo[1,2-a]pyridin-2-yl-anilide)
  参考文献：
  名称：

  Buu-Hoi; Khoi, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1950, vol. 230, p. 967

  摘要：

  DOI：
• 作为产物：
  描述：

  4-nitrophenacylpyridinium bromide 在 尿素 作用下， 生成 2-(4-硝基苯基)咪唑并[1,2-a]吡啶
  参考文献：
  名称：

  Microwave-Assisted, One-Pot Three Component Synthesis of 2-PhenylH-imidazo[1,2-α]pyridine

  摘要：

  描述了一种新颖的合成方法，通过在微波辐射和无溶剂条件下，将吡啶、胍嘧啶（尿素或硫脲）和α-溴酮进行一锅法三组分反应，得到了优异的产率的2-苯基H-咪唑[1,2-α]吡啶。

  DOI：

  10.1155/2012/198615

文献信息

• One pot synthesis of substituted imidazopyridines and thiazoles from styrenes in water assisted by NBS
  作者：Mahesh H. Shinde、Umesh A. Kshirsagar

  DOI：10.1039/c5gc02771c

  日期：——

  Heating of commercially available styrenes with NBS in water followed by reaction with 2-aminopyridines and thioamides afforded important heterocyclic scaffolds in a one pot procedure.

  将商业可获得的苯乙烯与NBS在水中加热，然后与2-氨基吡啶和硫代酰胺反应，在一锅法中得到重要的杂环骨架。
• Iodine-catalyzed regioselective sulfenylation of imidazoheterocycles in PEG₄₀₀
  作者：Marie-Aude Hiebel、Sabine Berteina-Raboin

  DOI：10.1039/c4gc01462f

  日期：——

  An iodine-catalyzed sulfenylation of imidazo[1,2-a]-pyridines, -pyrimidines, and [1,2-b]pyridazines is herein described with various thiophenols using hydrogen peroxide as an oxidizing agent in PEG400. The method enabled the formation of 3-arylthioimidazoheterocycles in moderate to excellent yields under metal-free conditions. Several functional groups were well tolerated under our optimized conditions

  本文描述了咪唑并[1,2- a ]-吡啶，-嘧啶和[1,2- b ]哒嗪的碘催化的亚磺酰基化，其中使用过氧化氢作为氧化剂在PEG 400中与各种硫酚一起使用。该方法能够在无金属条件下以中等至优异的产率形成3-芳基硫代咪唑并杂环。在我们优化的条件下，几个官能团的耐受性良好。
• Mechanism of the reaction of 2-haloketones with 2-aminopyridine
  作者：E. Smakula Hand、W.W. Paudler

  DOI：10.1016/0040-4020(82)85044-8

  日期：1982.1

  group enhances the rate of formation of C and D by a factor of only 2.6. The same rate enhancement is observed in the reaction of pyridine with phenacyl bromides. Rates of reaction of a given phenacyl halide with pyridine and 2-aminopyridine are similar. It is concluded that the initial reaction is alkylation of the pyridine nitrogen atom to give C and that the other possible initial condensation product

  对位取代的苯甲酰溴和2-氨基吡啶的DMSO-d 6溶液的时间依赖性1 H NMR光谱表明，咪唑并[1,2- a ]吡啶的形成是通过两种相对长寿的中间体C和D进行的，它们彼此平衡。指定的结构都与化学位移一致，PK一个的估计，以及取代基效应（-OMeCH 3，-H，和-NO 2在两个平衡常数（）Ç ⇌ d）和反应速度。与苯甲酰甲基溴反应最慢的步骤是将中间体转化d产品È。使用苯甲酰氯时，未观察到中间体，C的初始形成决定了总速率。即使通过中间体D已被质子化，其向E的转化也要经历酸催化作用。与p -OMe取代基相比，p -NO 2基团提高了C和D的形成速率仅为2.6。在吡啶与苯甲酰溴的反应中观察到相同的速率增加。给定的苯甲酰卤与吡啶和2-氨基吡啶的反应速率相似。可以得出结论，初始反应是吡啶氮原子的烷基化以生成C，而另一种可能的初始缩合产物甲醇胺F并不是动力学上重要的中间体。提出了优选的N-烷基化的原因。提出了改善咪唑并[1
• K2S2O8-Mediated halogenation of 2-arylimidazo[1,2-a]pyridines using sodium halides as the halogen sources
  作者：Praewpan Katrun、Chutima Kuhakarn

  DOI：10.1016/j.tetlet.2019.03.008

  日期：2019.4

  halogenation of 2-arylimidazo[1,2-a]pyridines using sodium chloride/bromide/iodide as the halogen sources in the presence of K2S2O8 as an easy-to-handle oxidizing agent was developed. The present work offers an efficient and rapid access to 3-chloro-, 3-bromo- and 3-iodo-2-arylimidazo[1,2-a]pyridines which can be readily converted to C3-substituted imidazo[1,2-a]pyridines by cross-coupling reactions.

  开发了在K 2 S 2 O 8作为易于处理的氧化剂存在下，使用氯化钠/溴化物/碘化物作为卤素源，方便地卤化2-芳基咪唑并[1,2- a ]吡啶的方法。本工作提供了一种快速有效地获得3-氯-，3-溴-和3-碘-2-芳基咪唑并[1,2- a ]吡啶的方法，这些吡啶基很容易转化为C 3取代的咪唑并[1,2] -一个]吡啶通过交叉偶联反应。
• Tandem [8 + 2] Cycloaddition−[2 + 6 + 2] Dehydrogenation Reactions Involving Imidazo[1,2-<i>a</i>]pyridines and Imidazo[1,2-<i>a</i>]pyrimidines
  作者：Maialen Aginagalde、Yosu Vara、Ana Arrieta、Ronen Zangi、Vicente L. Cebolla、Arantzazu Delgado-Camón、Fernando P. Cossío

  DOI：10.1021/jo9022815

  日期：2010.5.7

  The reaction between benzynes and imidazo[1,2-a]pyridines (pyrimidines) to form benzo[a]imidazo[5,1,2-cd]indolizines and 2,3,9c-triazocyclopenta[j,k]fluorenes has been studied computationally and experimentally. It is found that these reactions take place via tandem [π8s + π2s] and [σ2s + π6s + σ2s] processes. The [8 + 2] cycloaddition steps are essentially barrierless, and the aromatization steps

  苯并炔与咪唑并[1,2- a ]吡啶（嘧啶）之间形成苯并[ a ]咪唑并[5,1,2- cd ]吲哚并2,3,9c-三偶氮环戊[ j，k ]芴的反应通过计算和实验研究。据发现，这些反应通过串联发生[ π 8个小号+ π 2小号]和[ σ 2小号+ π 6小号+ σ 2个小号]流程。[8 + 2]环加成步骤基本无障碍，芳构化步骤通过高度同步的芳族过渡结构进行。从实验的角度来看，该反应在微波辐射下并且使用2-（三甲基甲硅烷基）苯基三氟甲磺酸酯作为苯炔前体是可行的。根据起始三氟甲磺酸酯的取代方式，可以实现反应的完全区域控制。如此制备的四环化合物在365 nm激发时发出蓝光，并表现出令人感兴趣的光物理性质。