5-硝基-N-苯基吡啶-2-胺 | 6825-25-8

• 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: 5-硝基-N-苯基吡啶-2-胺
• 英文名称: 5-nitro-N-phenylpyridin-2-amine
• 英文别名: 2-Anilino-5-nitro-pyridin；2-anilino-5-nitropyridine；5-Nitro-2-anilino-pyridin
• CAS: 6825-25-8
• 化学式: C₁₁H₉N₃O₂
• 分子量: 215.211
• InChiKey: NIPKIXLTWQXXEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.7
• 氢给体数：
  1
• 氢受体数：
  4

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: 5-Nitro-N-phenylpyridin-2-amine
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: 5-Nitro-N-phenylpyridin-2-amine
CAS number: 6825-25-8

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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: C11H9N3O2
Molecular weight: 215.2

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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：

  5-硝基-N-苯基吡啶-2-胺 在 溶剂黄146 、 sodium nitrite 作用下， 生成 (5-nitro-[2]pyridyl)-nitroso-phenyl-amine
  参考文献：
  名称：

  Bremer, Justus Liebigs Annalen der Chemie, 1935, vol. 518, p. 274,287

  摘要：

  DOI：
• 作为产物：
  描述：

  3-硝基吡啶 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 0.75h， 生成 5-硝基-N-苯基吡啶-2-胺
  参考文献：
  名称：

  3-Nitroyridine的SNH Arylamination：2-Arylamino-5-nitropyridines和2-Arylamino-5-nitrosopyridines的竞争形成

  摘要：

  摘要 通过氢的亲核取代对3-硝基吡啶进行的腺苷化反应产生了2-芳基氨基-5-硝基吡啶和新型的2-芳基氨基-5-亚硝基吡啶的混合物，后者是主要产物。所提出的机制包括σ的形成ħ -adducts或者通过氧化途径或分子内的S的红/牛途径和其进一步的芳构化程序Ñ ħ反应。此外，我们已经表明，亚硝基化合物可以与被选择性氧化米氯过苯甲酸，得到相应的硝基衍生物或它们的Ñ -oxides，这取决于反应温度和氧化剂的量。 通过氢的亲核取代对3-硝基吡啶进行的腺苷化反应产生了2-芳基氨基-5-硝基吡啶和新型的2-芳基氨基-5-亚硝基吡啶的混合物，后者是主要产物。所提出的机制包括σ的形成ħ -adducts或者通过氧化途径或分子内的S的红/牛途径和其进一步的芳构化程序Ñ ħ反应。此外，我们已经表明，亚硝基化合物可以与被选择性氧化米氯过苯甲酸，得到相应的硝基衍生物或它们的Ñ -oxides，这取决于反应温度和氧化剂的量。

  DOI：

  10.1055/s-0037-1610173

文献信息

• Copper anchored on phosphorus g-C₃N₄ as a highly efficient photocatalyst for the synthesis of <i>N</i>-arylpyridin-2-amines
  作者：Jia-Qi Di、Mo Zhang、Yu-Xuan Chen、Jin-Xin Wang、Shan-Shan Geng、Jia-Qi Tang、Zhan-Hui Zhang

  DOI：10.1039/d0gc03400b

  日期：——

  A copper modified phosphorus doped g-C₃N₄ (Cu/P-CN) has been prepared and identified as an efficient catalyst for the synthesis of N-arylpyridin-2-amine derivatives by the reaction of 2-aminopyridine and aryl boronic acid under the irradiation of blue light.

  一种经过铜改性的磷掺杂的g-C3N4（Cu/P-CN）已经制备并确定为一种高效催化剂，可用于在蓝光照射下通过2-氨基吡啶和芳基硼酸的反应合成N-芳基吡啶-2-胺衍生物。
• [EN] N- (6-AMINOPYRIDIN-3-YL) -3- (SULFONAMIDO) BENZAMIDE DERIVATIVES AS B-RAF INHIBITORS FOR THE TREATMENT OF CANCER<br/>[FR] DÉRIVÉS DE N-(6-AMINOPYRIDIN-3-YL)-3-(SULFONAMIDO) BENZAMIDE COMME INHIBITEURS DE B-RAF POUR LE TRAITEMENT DU CANCER
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2009111280A1

  公开（公告）日：2009-09-11

  Compounds of Formula (I) are useful for inhibition of Raf kinases. Methods of using compounds of Formula I and stereoisomers and pharmaceutically acceptable salts thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions are disclosed.

  式(I)的化合物对于抑制Raf激酶是有用的。本文揭示了利用式(I)的化合物及其立体异构体和药学上可接受的盐，在哺乳动物细胞中进行体外、体内和体内诊断、预防或治疗这些疾病，或相关病理条件的方法。
• Diarylamine Synthesis via Desulfinylative Smiles Rearrangement
  作者：Thomas Sephton、Jonathan M. Large、Sam Butterworth、Michael F. Greaney

  DOI：10.1021/acs.orglett.1c04122

  日期：2022.2.11

  Diarylamines are obtained directly from sulfinamides through a novel rearrangement sequence. The transformation is transition metal-free and proceeds under mild conditions, providing facile access to highly sterically hindered diarylamines that are otherwise inaccessible by traditional SNAr chemistry. The reaction highlights the distinct reactivity of the sulfinamide group in Smiles rearrangements

  二芳基胺是通过一种新的重排序列直接从亚磺酰胺中获得的。该转化不含过渡金属，在温和条件下进行，可轻松获得传统 S N Ar 化学无法获得的高度空间位阻二芳基胺。该反应突出了 Smiles 重排中的亚磺酰胺基团与更常见的磺酰胺的不同反应性。
• Solvent hydrogen bonding and structural effects on the reaction of 2-halo-5-nitropyridines with parasubstituted anilines in dimethylsulfoxide/acetonitrile mixtures
  作者：N. Kalaimani、S. Rathinam、D. S. Bhuvaneshwari

  DOI：10.1002/kin.20558

  日期：2011.8

  both the substrates. The solvation model proposed is well supported by the solvatochromism exhibited by aniline in the solvent mixture under investigation. The molar extinction coefficient (εmax ) of aniline varies appreciably up to ∼25% with the change in composition of the mixture. The multivariate correlation analysis of εmax  (with α, β, π*) suggests that the solvation around NH2 moiety of aniline

  一些对位取代的苯胺与2-氯-5-硝基吡啶和2-溴-5-硝基吡啶的取代反应在二甲基亚砜/乙腈混合物中进行电导测定。二阶速率常数与Hammett取代基常数的相关性产生具有负斜率的相当线性的直线。在两种底物中，速率数据与Kamlet-Taft的溶剂变色参数之间的相关性极佳（100R 2 = 97％）。所提出的溶剂化模型得到了苯胺在所研究的溶剂混合物中表现出的溶剂化显色性的充分支持。苯胺的摩尔消光系数（εmax ）随混合物组成的变化而变化约25％。εmax 的多元相关分析（具有α，β，π*）表明，通过氢键供体（HBD）性质在苯胺的NH 2部分周围的溶剂化在溶剂化过程中占主导地位，并因此改变了速率。观察结果是，通过溶剂混合物中苯胺的循环伏安氧化进一步证实了HBD在溶剂化中的优势。©2011 Wiley Peiodicals，Inc. Int J Chem Kinet 43：409-417，2011年
• Oxidative arylamination of 1,3-dinitrobenzene and 3-nitropyridine under anaerobic conditions: the dual role of the nitroarenes
  作者：Anna V. Gulevskaya、Inna N. Tyaglivaya、Stefan Verbeeck、Bert U. W. Maes、Anna V. Tkachuk

  DOI：10.3998/ark.5550190.0012.917

  日期：——

  Dinitrobenzene and 3-nitropyridine react with lithium arylamides under anaerobic conditions to produce N-aryl-2,4-dinitroanilines and N-aryl-5-nitropyridin-2-amines, respectively, in 8-42% yields.

  二硝基苯和 3-硝基吡啶在厌氧条件下与芳基酰胺锂反应，分别以 8-42% 的产率生成 N-芳基-2,4-二硝基苯胺和 N-芳基-5-硝基吡啶-2-胺。