3'-硝基-[1,1'-联苯基]-2-羧酸 | 37174-74-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3'-硝基-[1,1'-联苯基]-2-羧酸
• 中文别名: 2-(3-硝基苯基)苯甲酸
• 英文名称: 3'-nitro-[1,1'-biphenyl]-2-carboxylic acid
• 英文别名: 2-(3-Nitrophenyl)benzoic acid
• CAS: 37174-74-6
• 化学式: C₁₃H₉NO₄
• mdl: MFCD06803019
• 分子量: 243.219
• InChiKey: LGZSDFBCFHDCKP-UHFFFAOYSA-N

物化性质

• 熔点：
  260 °C (approx)
• 沸点：
  419.4±28.0 °C(Predicted)
• 密度：
  1.358±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 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：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2916399090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(3-Nitrophenyl)benzoic acid
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-(3-Nitrophenyl)benzoic acid
CAS number: 37174-74-6

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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: C13H9NO4
Molecular weight: 243.2

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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-[1,1'-联苯基]-2-羧酸 在 乙醇 、 铂 作用下， 生成 2-联苯-3-氨基-羧酸
  参考文献：
  名称：

  二苯基-2羧酸的氧化环化

  摘要：

  通过用铬酸或过氧化氢及其衍生物氧化，分解由该酸衍生的二酰基过氧化物并对其钠进行电解，可以完成二苯基-2羧酸脱氢成内酯（II； R = H）的反应。盐。从几种3'取代基（R = OMe，NHCOCH 3，CH，NO 2）对这些反应的影响，可以得出结论，铬酸和过氧化氢等的氧化是通过氧化剂与羧酸的连接而进行的。基团和相邻环中随后的阳离子类化合物取代。自由基（III）被认为是另外两个环化中的中间体。

  DOI：

  10.1016/0040-4020(57)88048-x
• 作为产物：
  描述：

  2-碘苯甲酸乙酯, 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 3'-硝基-[1,1'-联苯基]-2-羧酸
  参考文献：
  名称：

  Facile Preparation of 3,4-Benzocoumarins from 2-Arylbenzoic Acids with NCS and Nai

  摘要：

  Treatment of 2-arylbenzoic acids with N-chlorosuccinimide (NCS) and NaI at 70 degrees C under fluorescent lighting condition gave the corresponding 3,4-benzocoumarins in good yields under transition-metal-free condition. It was found that the reactivity of NCS with NaI for the formation of 3,4-benzocoumarins from 2-arylbenzoic acids was as high as that with NIS. Thus, the formation of carboxyl radicals and their cyclization onto an aromatic ring from 2-arylbenzoic acids with much less expensive NCS and NaI, than NIS could be successfully carried out to form 3,4-benzocoumarins.

  DOI：

  10.3987/com-20-14292

文献信息

• Cerium photocatalyzed dehydrogenative lactonization of 2-arylbenzoic acids
  作者：Ketan Wadekar、Suraj Aswale、Veera Reddy Yatham

  DOI：10.1039/c9ob02676b

  日期：——

  The first cerium photocatalyzed dehydrogenative lactonization of 2-arylbenzoic acids has been developed. This operationally simple protocol allows rapid access to synthetically useful coumarins on gram scale by employing CeCl3 as a photocatalyst and O2 as a terminal oxidant. Overall, this delivers an economical and environmentally amiable entry to diversely substituted coumarins, important structural

  已经开发出第一铈对2-芳基苯甲酸的光催化的脱氢内酯化。通过使用CeCl3作为光催化剂和O2作为末端氧化剂，这种操作简单的方案可以以克为单位快速获得合成有用的香豆素。总体而言，这为各种取代的香豆素提供了经济和环境友好的入口，香豆素是生物活性分子中的重要结构图案。
• A Practical Preparation of 2-Carboxyphenylboronic Acid and its Application for the Preparation of Biaryl-2-carboxylic Acids using Suzuki Coupling Reactions
  作者：Bin Tao、Subhash C. Goel、Jagvir Singh、David W. Boykin

  DOI：10.1055/s-2002-31954

  日期：——

  A practical synthesis of 2-carboxyphenylboronic from 2-tolylboronic acid and aqueous potassium permanganate under mild conditions is reported. The title compound couples with aryl bromides containing electron-withdrawing groups to give biaryl-2-carboxylic acids.

  报道了在温和条件下由 2-甲苯基硼酸和高锰酸钾水溶液合成 2-羧基苯基硼酸的方法。标题化合物与含有吸电子基团的芳基溴化物偶联生成联芳基-2-羧酸。
• Mechanochemical-Cascaded C–N Cross-Coupling and Halogenation Using <i>N</i>-Bromo- and <i>N</i>-Chlorosuccinimide as Bifunctional Reagents
  作者：Shyamal Kanti Bera、Prasenjit Mal

  DOI：10.1021/acs.joc.1c01742

  日期：2021.10.15

  gained significant interest from chemists, and mechanochemistry is one of those sources. Herein, we report the use of N-bromosuccinimides (NBS) and N-chlorosuccinimides (NCS) as bifunctional reagents for a cascaded C–N bond formation and subsequent halogenation reactions. Under the solvent-free mechanochemical (ball-milling) conditions, the synthesis of a wide range of phenanthridinone derivatives from

  化学转化替代能源的探索引起了化学家的极大兴趣，机械化学就是其中之一。在此，我们报告了使用N-溴代琥珀酰亚胺 (NBS) 和N-氯代琥珀酰亚胺 (NCS) 作为双功能试剂用于级联 C-N 键形成和随后的卤化反应。在无溶剂机械化学（球磨）条件下，从N合成多种菲啶酮衍生物-甲氧基-[1,1'-联苯]-2-甲酰胺完成。在反应过程中，NBS 和 NCS 首先辅助氧化 C-N 偶联反应，随后促进卤化反应。因此，NBS 和 NCS 的作用被确立为双功能。总体而言，实现了各种溴代和氯代菲啶酮衍生物的温和、无溶剂、方便、一锅法和直接合成。
• General and Practical Carboxyl-Group-Directed Remote CH Oxygenation Reactions of Arenes
  作者：Yang Wang、Anton V. Gulevich、Vladimir Gevorgyan

  DOI：10.1002/chem.201303511

  日期：2013.11.18

  Two methods for remote aromatic CH oxygenation reactions, have been developed. Method 1, the Cu‐catalyzed oxygenation reaction, is highly efficient for cyclization of electron‐neutral and electron‐rich biaryl carboxylic acids into 3,4‐benzocoumarins. Method 2, the K2S2O8‐mediated oxygenation reaction, is more general and practical for cyclization of substrates with electron‐donating and ‐withdrawing

  已经开发了两种用于远程芳族 C  H 氧化反应的方法。方法 1，即 Cu 催化的氧化反应，对于将电子中性和富电子的联芳基羧酸环化为 3,4-苯香豆素非常有效。方法 2，K 2 S 2 O 8介导的氧化反应，对于具有给电子和吸电子基团的底物的环化更为通用和实用（见方案）。
• Makarowa et al., Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1958, p. 1452,1457; engl. Ausg. S. 1399, 1404
  作者：Makarowa et al.

  DOI：——

  日期：——