4-硝基[1,1-联苯]-2-羧酸 | 18211-41-1

• 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: 4-硝基[1,1-联苯]-2-羧酸
• 中文别名: 2-(4-硝基苯基)苯甲酸
• 英文名称: 4'-nitro-[1,1'-biphenyl]-2-carboxylic acid
• 英文别名: 2-(4-Nitrophenyl)benzoic acid
• CAS: 18211-41-1
• 化学式: C₁₃H₉NO₄
• 分子量: 243.219
• InChiKey: IVKKQTQLZURECG-UHFFFAOYSA-N

物化性质

• 熔点：
  228-230°C
• 沸点：
  420.4±20.0 °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

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2916399090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(4-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-(4-Nitrophenyl)benzoic acid
CAS number: 18211-41-1

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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：

  4-硝基[1,1-联苯]-2-羧酸 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 4'-氨基-2-联苯基羧酸
  参考文献：
  名称：

  V1A和V2受体的非肽精氨酸加压素拮抗剂：2-苯基-4'-[（2,3,4,5-四氢-1H-1-苯并ze庚-1-基）羰基]苯甲腈衍生物的合成和药理特性。

  摘要：

  合成了一系列在结构上与4'-[（2,3,4,5-四氢-1H-1-苯并ze庚因-1-基）羰基]苯并ili啶有关的化合物，并证明它们具有精氨酸加压素（AVP）拮抗剂活性V1A和V2受体。将苯基或4-取代的苯基引入苯甲酰基部分的邻位导致结合亲和力和拮抗活性均增加。与2-甲基铅化合物相比，2-（4-甲基苯基）衍生物（1g）对V1A（8.6倍）和V2（38倍）受体均具有高拮抗活性，并且对口服活性（8.6倍）也较高（ 1a）。介绍了该系列的合成细节和药理特性。

  DOI：

  10.1248/cpb.45.1870
• 作为产物：
  描述：

  1-甲基-2-(4-硝基苯基)苯 在 potassium permanganate 作用下， 以 吡啶 、 水 为溶剂， 生成 4-硝基[1,1-联苯]-2-羧酸
  参考文献：
  名称：

  设计和合成非肽Ras CAAX模拟物作为有效的法呢基转移酶抑制剂。

  摘要：

  ras癌基因产物Ras的半胱氨酸法呢基化对于其转化活性是必需的，并且被法呢基转移酶（FTase）催化。Ras羧基末端四肽CAAX（C是半胱氨酸，A是任何脂肪族氨基酸，X是蛋氨酸或丝氨酸）是FTase识别的最小序列。我们在这里报告Ras CAAX非肽模拟物的设计，合成和生物学特性，其中半胱氨酸通过还原的伪肽键与4-氨基-3'-羧基联苯相连。这些非肽模拟物是FTase的有效抑制剂（IC50 = 40 nM，是最有效的抑制剂），对FTase的选择性高于GGTase I（香叶基香叶基转移酶I）。它们不是法呢基化的底物，没有肽特征，也没有可水解键。结构活性研究揭示了芳基环上羧酸位置以及半胱氨酸酰胺键还原的重要性。在4-氨基-3'-羧基联苯的2-位取代可提高抑制能力，而羧酸的去除则会导致抑制活性降低10倍。

  DOI：

  10.1021/jm950414g
• 作为试剂：
  描述：

  (2S,4S)-1,5-dichloro-2,4-pentanediol 在 正丁基锂 、 4-硝基[1,1-联苯]-2-羧酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (1R,4S)-(-)-4-triisopropylsilyloxy-1-hydroxycyclopent-2-ene
  参考文献：
  名称：

  Synthesis of cyclic 1,3-diols as scaffolds for spatially directed libraries

  摘要：

  一系列1,3-二醇已经合成并用于创建一个空间多样化化合物的试验库。

  DOI：

  10.1039/c6ob00598e

文献信息

• CATALYTIC ESTER DECARBONYLATION
  申请人：Tolman William Baker

  公开号：US20160194276A1

  公开（公告）日：2016-07-07

  A process of preparing olefins of the formula (I) is described herein: with R 1 being a substituted or unsubstituted (C 1 -C 30 )hydrocarbyl, and R 2 being a substituted or unsubstituted (C 1 -C 20 )hydrocarbyl. The process includes reacting a compound of formula (II) wherein Ar is chosen from in the presence of a palladium-based catalyst and an organic solvent. A process of preparing olefins of the formula (III) is also described: with R 3 being a substituted or unsubstituted (C 1 -C 30 )hydrocarbyl, R 4 being a substituted or unsubstituted (C 1 -C 20 )hydrocarbyl, and R 5 being a substituted or unsubstituted (C 1 -C 30 ) hydrocarbyl. The process includes reacting a compound of formula (IV) wherein Ar is chosen from with a compound of formula (V) wherein Ar is chosen from in the presence of a palladium-based catalyst and an organic solvent.

  本文描述了一种制备具有化学式（I）的烯烃的过程： 其中R1是取代或未取代的（C1-C30）烃基，R2是取代或未取代的（C1-C20）烃基。该过程包括在钯基催化剂和有机溶剂的存在下，反应具有化学式（II）的化合物 其中Ar选择自 。还描述了一种制备具有化学式（III）的烯烃的过程： 其中R3是取代或未取代的（C1-C30）烃基，R4是取代或未取代的（C1-C20）烃基，R5是取代或未取代的（C1-C30）烃基。该过程包括在钯基催化剂和有机溶剂的存在下，反应具有化学式（IV）的化合物 其中Ar选择自 与具有化学式（V）的化合物 其中Ar选择自 。
• Electrochemical C−O Bond Formation: Facile Access to Aromatic Lactones
  作者：Xiang-Zhang Tao、Jian-Jun Dai、Jie Zhou、Jun Xu、Hua-Jian Xu

  DOI：10.1002/chem.201801108

  日期：2018.5.11

  An efficient and robust methodology based on electrochemical techniques for the direct synthesis of aromatic lactones through dehydrogenative C−O cyclization is described. This new and useful electrochemical reaction can tolerate a variety of functional groups, and is scalable to 100 g under mild conditions. Remarkably, heterocycle‐containing substrates can be employed, thus expanding the scope of

  描述了一种基于电化学技术的有效且稳健的方法，用于通过脱氢C-O环化反应直接合成芳族内酯。这种新的有用的电化学反应可以耐受各种官能团，在温和条件下可扩展至100 g。值得注意的是，可以使用含杂环的底物，从而扩大了自由基C-O环化反应的范围。
• 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。
• 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）。
• Nonpeptide Arginine Vasopressin Antagonists for Both V1A and V2 Receptors: Synthesis and Pharmacological Properties of 2-Phenyl-4'-((2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl)benzanilide Derivatives.
  作者：Akira MATSUHISA、Akihiro TANAKA、Kazumi KIKUCHI、Yoshiaki SHIMADA、Takeyuki YATSU、Isao YANAGISAWA

  DOI：10.1248/cpb.45.1870

  日期：——

  A series of compounds structurally related to 4'-[(2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl]benzanili de was synthesized and demonstrated to have arginine vasopressin (AVP) antagonist activity for both V1A and V2 receptors. The introduction of a phenyl or a 4-substituted phenyl group into the ortho position of the benzoyl moiety resulted in an increase in both binding affinity and antagonistic

  合成了一系列在结构上与4'-[（2,3,4,5-四氢-1H-1-苯并ze庚因-1-基）羰基]苯并ili啶有关的化合物，并证明它们具有精氨酸加压素（AVP）拮抗剂活性V1A和V2受体。将苯基或4-取代的苯基引入苯甲酰基部分的邻位导致结合亲和力和拮抗活性均增加。与2-甲基铅化合物相比，2-（4-甲基苯基）衍生物（1g）对V1A（8.6倍）和V2（38倍）受体均具有高拮抗活性，并且对口服活性（8.6倍）也较高（ 1a）。介绍了该系列的合成细节和药理特性。