9-(4-硝基苯基)-9H-咔唑 | 16982-76-6

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 9-(4-硝基苯基)-9H-咔唑
• 中文别名: 9-(4-硝基苯)-9H-咔唑
• 英文名称: 9-(4-nitrophenyl)-9H-carbazole
• 英文别名: N-(4-nitrophenyl)carbazole；9-(p-Nitrophenyl)-carbazol；9-(4-nitrophenyl)carbazole
• CAS: 16982-76-6
• 化学式: C₁₈H₁₂N₂O₂
• mdl: MFCD00159886
• 分子量: 288.305
• InChiKey: CDGXAOCJQUZBID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 9-(4-Nitrophenyl)carbazole
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: 9-(4-Nitrophenyl)carbazole
CAS number: 16982-76-6

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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: C18H12N2O2
Molecular weight: 288.3

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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：

  9-(4-硝基苯基)-9H-咔唑 在 palladium on activated charcoal 、 溶剂黄146 、 肼 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 42.0h， 生成
  参考文献：
  名称：

  包含未取代的芳基氨基部分和偶氮苯单元的有机染料，用于染料敏化太阳能电池

  摘要：

  利用偶氮苯作为D–π–A结构的π键单元成功合成了一系列新型敏化剂。当将噻吩基基团引入受体部分（A）时，可以观察到敏化剂的吸收光谱和λ起始出现轻微的红移。此外，将咔唑的供体部分（D）替换为二芳基氨基可能导致第一氧化电位发生负移（约0.3 V）。还进行了DFT计算，计算出的HOMO-LUMO缺口趋势与从CV结果获得的实验数据一致（DT1  <  DT2  <  DT3  <  DT4）。然后将这些敏化剂用于染料敏化太阳能电池中，以研究其光伏性能。基于DT1的DSSC的最大红移吸收光谱，其最高功率转换效率（PCE）为0.84％。

  DOI：

  10.1002/jccs.201900204
• 作为产物：
  描述：

  4-硝基苯胺 在 溶剂黄146 作用下， 反应 28.0h， 生成 9-(4-硝基苯基)-9H-咔唑
  参考文献：
  名称：

  Synthesis of Heteroaromatic Derivatives with Nitrogen Atoms: Tripyrrolyl Pyrimidine and Tripyrrolyl[1,3,5]triazine

  摘要：

  作为药理学和光电导有趣的吡咯衍生物合成研究计划的一部分，我们合成了 1-芳基吡咯（3a-e）、9-芳基咔唑（4a-e）、氨基苯基吡咯（6a,b）、二吡咯基苯（7a-c）、2,4,6-三吡咯-1-基嘧啶（8）和 2,4,6-三吡咯-1-基[1,3,5]三嗪（9）。我们提出了 9-芳基咔唑的合理生成机制。

  DOI：

  10.14233/ajchem.2013.13307

文献信息

• The Suzuki–Miyaura Coupling of Nitroarenes
  作者：M. Ramu Yadav、Masahiro Nagaoka、Myuto Kashihara、Rong-Lin Zhong、Takanori Miyazaki、Shigeyoshi Sakaki、Yoshiaki Nakao

  DOI：10.1021/jacs.7b03159

  日期：2017.7.19

  Synthesis of biaryls via the Suzuki-Miyaura coupling (SMC) reaction using nitroarenes as an electrophilic coupling partners is described. Mechanistic studies have revealed that the catalytic cycle of this reaction is initiated by the cleavage of the aryl-nitro (Ar-NO2) bond by palladium, which represents an unprecedented elemental reaction.

  描述了通过 Suzuki-Miyaura 偶联 (SMC) 反应使用硝基芳烃作为亲电偶联伙伴合成联芳基化合物。机理研究表明，该反应的催化循环是由钯对芳基-硝基 (Ar-NO2) 键的裂解引发的，这是一种前所未有的元素反应。
• Manganese-Mediated Reductive Transamidation of Tertiary Amides with Nitroarenes
  作者：Chi Wai Cheung、Jun-An Ma、Xile Hu

  DOI：10.1021/jacs.8b03739

  日期：2018.6.6

  an important class of organic compounds, which have widespread industrial applications. Transamidation of amides is a convenient method to generate new amides from existing ones. Tertiary amides, however, are challenging substrates for transamidation. Here we describe an unconventional approach to the transamidation of tertiary amides using nitroarenes as the nitrogen source under reductive conditions

  酰胺是一类重要的有机化合物，具有广泛的工业应用。酰胺的转酰胺是一种从现有酰胺生成新酰胺的便捷方法。然而，叔酰胺对于转酰胺基作用是具有挑战性的底物。在这里，我们描述了一种在还原条件下使用硝基芳烃作为氮源的叔酰胺转酰胺的非常规方法。金属锰单独介导反应，不需要额外的催化剂。该方法表现出广泛的范围和高官能团耐受性。
• Amide synthesis <i>via</i> nickel-catalysed reductive aminocarbonylation of aryl halides with nitroarenes
  作者：Chi Wai Cheung、Marten Leendert Ploeger、Xile Hu

  DOI：10.1039/c7sc03950f

  日期：——

  Aminocarbonylation of aryl halides is one of the most useful methods in amide synthesis, but nitroarenes have not been used as a nitrogen source in this method even though they are more economical and accessible than anilines. Reported here is the development of nickel catalysis for the first three-component reactions of aryl halides, Co2(CO)8, and nitroarenes under reductive conditions to produce aryl amides. A

  芳基卤化物的氨基羰基化是酰胺合成中最有用的方法之一，但是硝基芳烃虽然比苯胺更经济，更易获得，但在该方法中并未用作氮源。此处报道的是在还原条件下，芳基卤化物，Co 2（CO）8和硝基芳烃在头三组分反应中生成镍酰胺的镍催化的进展。广泛的（杂）芳基碘化物和溴化物以及硝基（杂）芳烃是合适的反应伙伴，并且已经实现了高官能团相容性。该方法可用于芳基酰胺的流线型合成。
• Copper-coordination polymer-controlled Cu@N-rGO and CuO@C nanoparticle formation: reusable green catalyst for A³-coupling and nitroarene-reduction reactions
  作者：Vadivel Vinod Kumar、Rajamani Rajmohan、Pothiappan Vairaprakash、Mariappan Mariappan、Savarimuthu Philip Anthony

  DOI：10.1039/c7dt02119d

  日期：——

  structural properties of coordination polymers (COPs), together with the huge variety of metal ions and organic linkers to choose from, make COPs potential precursors for fabricating carbon-encapsulated metal and metal oxide nanoparticles (NPs). Herein, we have studied the role of the COP structural assembly, prepared through making subtle changes to the ligand structure, on the formation of NPs in

  配位聚合物（COP）令人着迷的结构特性，以及可供选择的多种金属离子和有机连接剂，使COPs成为制造碳封装的金属和金属氧化物纳米颗粒（NP）的潜在前体。本文中，我们研究了通过对配体结构进行细微变化而制备的COP结构组装对碳基质中NP形成的作用。使用不同的基于氨基酸的还原席夫碱酚类螯合配体生成的铜-COP（Cu-COP-1–Cu-COP-7）在固态下显示出具有不同结构组织的晶体结构。有趣的是，在330°C下煅烧Cu-COP-1和Cu-COP-5可产生纯CuNP，而Cu-COP-2，Cu-COP-3，Cu-COP-4和Cu-COP-7生成了被碳基质包裹的CuONP。Cu-COP-6的煅烧在碳基质中同时产生了CuNPs和CuONPs。通过PXRD和XPS研究明确证实了碳基质中CuNP和CuONP的形成。使用HR-TEM和FE-SEM分析了Cu / CuONP的大小和形态。BET研究表明，碳包裹的C
• 축합환 화합물, 및 이를 포함한 유기 발광 소자
  申请人：SAMSUNG SDI CO., LTD. 삼성에스디아이 주식회사(119980018058) Corp. No ▼ 110111-0394174BRN ▼124-81-31282

  公开号：KR20150084657A

  公开（公告）日：2015-07-22

  축합환 화합물 및 상기 축합환 화합물을 포함한 유기 발광 소자가 제시된다.

  有机发光器件包括聚合环化合物和上述聚合环化合物。