3-(1H-吡唑-1-基)苯甲腈 | 25699-82-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(1H-吡唑-1-基)苯甲腈
• 英文名称: 3-pyrazolylbenzonitrile
• 英文别名: 3-(pyrazol-1-yl)benzonitrile；1-(3-cyanophenyl)pyrazole；N-(3-cyanophenyl)pyrazole；3-(1H-pyrazol-1-yl)benzonitrile；1-m-Cyanophenyl-pyrazol；3-pyrazol-1-ylbenzonitrile
• CAS: 25699-82-5
• 化学式: C₁₀H₇N₃
• mdl: MFCD07772807
• 分子量: 169.186
• InChiKey: KLZKYUMVLIQOFX-UHFFFAOYSA-N

物化性质

• 沸点：
  309.8±25.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933199090
• 储存条件：
  | 室温 |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-(1H-Pyrazol-1-yl)benzonitrile
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-(1H-Pyrazol-1-yl)benzonitrile
CAS number: 25699-82-5

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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, 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: C10H7N3
Molecular weight: 169.2

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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-(1H-吡唑-1-基)苯甲腈 在 盐酸 、 [(1,2,3,4,5-pentamethylcyclopentadienyl)*Co(CH₃CN)₃](SbF₆)₂ 作用下， 以 1,2-二氯乙烷 为溶剂， 23.0~100.0 ℃ 、101.33 kPa 条件下， 反应 25.5h， 生成 4-ethoxy-2-phenyl-6-(1H-pyrazol-1-yl)quinazoline
  参考文献：
  名称：

  通过钴催化克服CH-活化与强配位N-杂环的局限性

  摘要：

  在钴催化的CHH酰胺化反应中，通过亚氨酸盐的辅助作用，可以完全耐受包括嘧啶，恶唑啉，吡唑和吡啶在内的强配位氮杂环。因此，结构经济的喹唑啉可以逐步经济地获得。我们的发现还首次确定了钴（II​​I）催化的CH官能团中的导向基团的相对能力。

  DOI：

  10.1002/anie.201603260
• 作为产物：
  描述：

  1-(3-硝基苯基)-1H-吡唑 在 palladium on activated charcoal 盐酸 、 一水合肼 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 1.33h， 生成 3-(1H-吡唑-1-基)苯甲腈
  参考文献：
  名称：

  Solvent-free preparation of tris-pyrazolyl-1,3,5-triazines

  摘要：

  Tris-pyrazolyl-1,3,5-triazines have been prepared by cyclotrimerization of aromatic nitriles in solvent-free conditions. The interesting structures of these compounds make them candidates for application in coordination chemistry and crystal engineering. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00340-4

文献信息

• <scp>l</scp><i>-</i>(<i>−</i>)<i>-</i>Quebrachitol as a Ligand for Selective Copper(0)-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles
  作者：Qifan Zhou、Fangyu Du、Yuanguang Chen、Yang Fu、Wenjiao Sun、Ying Wu、Guoliang Chen

  DOI：10.1021/acs.joc.9b00997

  日期：2019.6.21

  l-(−)-Quebrachitol (QCT) has been found as a ligand of copper powder for selective N-arylation of nitrogen-containing heterocycles with aryl halides. Furthermore, another potential catalytic system (copper powder/QCT/t-BuOK) was successfully adapted to unactivated aryl chlorides.

  已经发现1 -（-）-木糖醇（QCT）作为铜粉的配体，用于含氮杂环与芳基卤化物的选择性N-芳基化。此外，另一种潜在的催化体系（铜粉/ QCT / t- BuOK）已成功地用于未活化的芳基氯化物。
• Copper-Catalyzed Arylation of Nitrogen Heterocycles from Anilines under Ligand-Free Conditions
  作者：Dounia Toummini、Anis Tlili、Julien Bergès、Fouad Ouazzani、Marc Taillefer

  DOI：10.1002/chem.201404982

  日期：2014.11.3

  The arylation of pyrazole and derivatives can be achieved by coupling arenediazonium species (formed in situ from anilines) by using a catalytic system that employs low‐toxicity and inexpensive copper metal under very mild and ligand‐free conditions (T=20 °C). From other nitrogen heterocycles, the presence of an additive (NBu4I) significantly improves the efficiency of the catalytic system. These results

  吡唑和衍生物的芳基化反应可以通过使用催化系统偶联槟榔重氮物种（由苯胺原位形成）来实现，该催化系统在非常温和且无配体的条件下（T = 20°C）使用低毒性和廉价的铜金属。与其他氮杂环相比，添加剂（NBu 4 I）的存在可显着提高催化体系的效率。这些结果代表C的第一实施例从芳基重氮物种N键的形成。
• An Ullmann Coupling of Aryl Iodides and Amines Using an Air-Stable Diazaphospholane Ligand
  作者：Minghua Yang、Fei Liu

  DOI：10.1021/jo0712291

  日期：2007.11.1

  A copper-based catalytic system, using an air-stable diazaphospholane as the ligand, was developed for an efficient Ullmann reaction between aryl iodides and alkyl or heterocyclic amines.

  为了使芳基碘化物与烷基或杂环胺发生有效的乌尔曼反应，开发了一种使用空气稳定的二氮杂膦烷作为配体的铜基催化体系。
• Green synthesis and self-association of 2,4-diamino-1,3,5-triazine derivatives
  作者：Ángel Díaz-Ortiz、José Elguero、Concepción Foces-Foces、Antonio de la Hoz、Andrés Moreno、María del Carmen Mateo、Ana Sánchez-Migallón、Gema Valiente

  DOI：10.1039/b315956f

  日期：——

  2,4-Diamino-1,3,5-triazines have been prepared by reaction of dicyandiamide with nitriles under microwave irradiation, a method that can be considered as a green procedure due to the reduction in the use of solvents during synthesis and purification, the short reaction time and the simplicity of the procedure. The structures have been confirmed in solution by NMR spectroscopy. Variable temperature experiments have been used to calculate the free energy of activation for rotation about the amino–triazine bond. The crystal structures of three 2,4-diamino-6-R-1,3,5-triazine derivatives (3a: R = phenyl, 3i: R = 1-piperidino and 3g: R = 1-phenylpyrazol-3-yl) have been determined by X-ray analysis. The N–H⋯N interactions change from structure to structure, resulting in a variation from pseudo-honeycomb networks to corrugated rosette layers.

  2,4-二氨基-1,3,5-三嗪是通过在微波照射下将二氰胺与腈类反应制备的，这种方法可以被视为一种绿色程序，因为在合成和纯化过程中减少了溶剂的使用，反应时间短且过程简单。通过NMR光谱在溶液中确认了其结构。可变温度实验用于计算关于氨基-三嗪键旋转的活化自由能。三种2,4-二氨基-6-R-1,3,5-三嗪衍生物（3a: R=苯基, 3i: R=1-哌啶基和3g: R=1-苯基吡唑-3-基）的晶体结构已通过X射线分析确定。N–H⋯N相互作用因结构的不同而变化，导致从伪蜂窝网络到波纹玫瑰层的变化。
• Microwave assisted synthesis and crystal structures of 2-imidazolines and imidazoles
  作者：Antonio de la Hoz、Ángel Díaz-Ortiz、María del Carmen Mateo、Mónica Moral、Andrés Moreno、José Elguero、Concepción Foces-Foces、Matías L. Rodríguez、Ana Sánchez-Migallón

  DOI：10.1016/j.tet.2006.04.020

  日期：2006.6

  A series of 2-imidazolines and imidazoles has been synthesized using green synthetic methodologies. The preparation of 2-imidazolines was performed by cyclization of nitriles with ethylenediamine. The use of microwave irradiation in solvent-free conditions enabled 2-imidazolines to be obtained in high yields within short reaction times. Aromatization of imidazoles was performed under microwave irradiation

  已经使用绿色合成方法合成了一系列的2-咪唑啉和咪唑。2-咪唑啉的制备是通过用乙二胺环化腈而进行的。在无溶剂的条件下使用微波辐照使得能够在短的反应时间内以高收率获得2-咪唑啉。咪唑的芳香化反应是在甲苯中微波辐射下并使用Magtrieve™作为氧化剂进行的。提供了这些衍生物中的五个的X射线结构。在所有情况下，分子都通过N–H⋯N氢键组装成链。