4’-硝基联苯-4-羧酸 | 92-89-7

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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’-硝基联苯-4-羧酸
• 中文别名: 4-(4'-硝基苯基)苯甲酸；4-硝基-4-羧基联苯；4-(4"-硝基苯基)苯甲酸；4'-硝基联苯-4-羧酸
• 英文名称: 4'-nitro-biphenyl-4-carboxylic acid
• 英文别名: 4'-Nitrobiphenyl-4-carboxylic acid；4’-nitro[1,1’-biphenyl]-4-carboxylic acid；4′-nitro[1,1′-biphenyl]-4-carboxylic acid；4'-nitro-(1,1'-biphenyl)-4-carboxylic acid；4’-nitrobiphenyl-4-carboxylic acid；4'-nitro[1,1'-biphenyl]-4-carboxylic acid；[1,1'-Biphenyl]-4-carboxylic acid, 4'-nitro-；4-(4-nitrophenyl)benzoic acid
• CAS: 92-89-7
• 化学式: C₁₃H₉NO₄
• 分子量: 243.219
• InChiKey: LYINHPAEAYJDIR-UHFFFAOYSA-N

物化性质

• 熔点：
  350°
• 沸点：
  450.2±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)：
  3.5
• 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
• 海关编码：
  2916399090
• 储存条件：
  存储条件：室温、干燥且密封。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(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: 4-(4-Nitrophenyl)benzoic acid
CAS number: 92-89-7

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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’-硝基联苯-4-羧酸 在 盐酸 、 氢氧化钾 、 铁粉 作用下， 以 甲醇 为溶剂， 生成 4’-氨基-4-联苯基羧酸
  参考文献：
  名称：

  一些取代的联苯-4-羧酸，4-联苯基乙酸和4-氨基联苯的合成

  摘要：

  描述了一系列取代的联苯-4-羧酸和4-氨基联苯的合成。包括母体联苯-4-羧酸，4-联苯基乙酸和三种取代的4-联苯基乙酸的制剂。

  DOI：

  10.1039/j39660000840
• 作为产物：
  描述：

  4-甲基-4'-硝基联苯 在 potassium permanganate 作用下， 以 吡啶 、 水 为溶剂， 生成 4’-硝基联苯-4-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

文献信息

• Copper catalyzed cross-coupling reactions of carboxylic acids: an expedient route to amides, 5-substituted γ-lactams and α-acyloxy esters
  作者：S. Priyadarshini、P. J. Amal Joseph、M. Lakshmi Kantam

  DOI：10.1039/c3ra41000e

  日期：——

  A convenient and recyclable catalytic protocol for the synthesis of N,N-dimethyl substituted amides, 5-substituted γ-lactams and α-acyloxy ethers from carboxylic acids using CuO nanoparticles and TBHP is described.

  描述了使用CuO纳米颗粒和TBHP从羧酸合成N，N-二甲基取代的酰胺，5-取代的γ-内酰胺和α-酰氧基醚的方便且可回收的催化方案。
• Design, Synthesis, and Evaluation of Novel Immunomodulatory Small Molecules Targeting the CD40–CD154 Costimulatory Protein-Protein Interaction
  作者：Damir Bojadzic、Jinshui Chen、Oscar Alcazar、Peter Buchwald

  DOI：10.3390/molecules23051153

  日期：——

  We report the design, synthesis, and testing of novel small-molecule compounds targeting the CD40⁻CD154 (CD40L) costimulatory interaction for immunomodulatory purposes. This protein-protein interaction (PPI) is a TNF-superfamily (TNFSF) costimulatory interaction that is an important therapeutic target since it plays crucial roles in the activation of T cell responses, and there is resurgent interest

  我们报告针对免疫调节目的针对CD40CDCD154（CD40L）共刺激相互作用的新型小分子化合物的设计，合成和测试。这种蛋白质-蛋白质相互作用（PPI）是TNF超家族（TNFSF）的共刺激相互作用，是重要的治疗靶标，因为它在T细胞反应的激活中起着关键作用，并且人们对它在多种生物制剂的调控中的兴起兴趣不断。但是，与所有其他PPI一样，这种相互作用很难被小分子靶向。继我们之前的工作之后，我们现已鉴定出新的化合物，例如DRI-C21091或DRI-C21095，它们在结合抑制测定中的高纳摩尔至低微摩尔范围内显示活性（IC50），选择性是其他化合物的三十倍以上TNFSF PPI，包括OX40⁻OX40L，BAFFR-BAFF，和TNF-R1-TNFα。蛋白质热位移（差示扫描荧光法）分析表明CD154而非CD40为结合伴侣。在细胞测定法和小鼠模型中也证实了活性（在引流淋巴结中由抗原诱导的T细胞扩增）
• Small-Molecule Inhibitors of the CD40–CD40L Costimulatory Protein–Protein Interaction
  作者：Jinshui Chen、Yun Song、Damir Bojadzic、Alejandro Tamayo-Garcia、Ana Marie Landin、Bonnie B. Blomberg、Peter Buchwald

  DOI：10.1021/acs.jmedchem.7b01154

  日期：2017.11.9

  Costimulatory interactions are required for T cell activation and development of an effective immune response; hence, they are valuable therapeutic targets for immunomodulation. However, they, as all other protein–protein interactions, are difficult to target by small molecules. Here, we report the identification of novel small-molecule inhibitors of the CD40–CD40L interaction designed starting from

  共刺激相互作用是T细胞活化和发展有效免疫反应所必需的；因此，它们是免疫调节的有价值的治疗靶标。但是，它们与所有其他蛋白质-蛋白质相互作用一样，很难被小分子靶向。在这里，我们报告了从有机染料的化学空间出发设计的新型CD40–CD40L相互作用小分子抑制剂的鉴定。对于最有前途的化合物（例如DRI-C21045），活性（IC 50）已在细胞试验中证实了在低微摩尔范围内的抑制作用，包括在NF-κB传感器细胞，THP-1髓样细胞和原代人B细胞以及小鼠同种异体皮肤移植和同种异体抗原诱导的T中抑制CD40L诱导的活化引流淋巴结实验中的细胞扩增。在这些浓度下，也证实了特异性相对于其他TNF超家族相互作用（TNF-R1-TNF-α）的缺乏细胞毒性。这些新颖的化合物提供了小分子抑制共刺激蛋白-蛋白相互作用的可能性的原理证据，确立了有效抑制CD40-CD40L所需的结构要求，并指导寻找此类免疫疗法。
• Organic Solvent-Free, Pd(II)-Salan Complex-Catalyzed Synthesis of Biaryls via Suzuki–Miyaura Cross-Coupling in Water and Air
  作者：Szilvia Bunda、Antal Udvardy、Krisztina Voronova、Ferenc Joó

  DOI：10.1021/acs.joc.8b02340

  日期：2018.12.21

  Pd(II)-sulfosalan complex as a water-soluble catalyst, we have developed an efficient synthesis of biaryls via Suzuki–Miyaura cross-coupling in water under aerobic conditions. The water-insoluble target molecules were isolated by simple filtration in analytical purity after washing with 0.01 M aqueous HCl (20 examples). In most cases, palladium contamination was below 5 ppm considered acceptable for active pharmaceutical

  通过使用Pd（II）-磺基磺酸盐络合物作为水溶性催化剂，我们在有氧条件下通过Suzuki-Miyaura交叉偶联开发了一种有效的联芳基合成方法。用0.01M HCl水溶液洗涤后，通过简单过滤以分析纯度分离水不溶性目标分子（20个实施例）。在大多数情况下，活性药物成分可接受的钯污染低于5 ppm。既定的方法是可扩展的，可重现的，并提供高达91％的分离产率的联芳基产品。
• Copper chelators
  申请人：Farma-Derma S.R.L.

  公开号：EP2927215A1

  公开（公告）日：2015-10-07

  The present invention relates to a new class of chemical compounds of structure 6,7-dimethoxy-1,2,3,4-tetra-hydro-isoquinoline having therapeutic action, processes for the synthesis thereof and formulations containing said derivatives. More particularly, the present invention relates to ligand compounds adapted for chelating the free cupric ion in the serum of patients suffering from Alzheimer's and Wilson's diseases.

  这项发明涉及一类新的化合物，其结构为6,7-二甲氧基-1,2,3,4-四氢异喹啉，具有治疗作用，以及用于合成这些化合物和含有这些衍生物的配方的方法。更具体地，这项发明涉及适用于螯合患有阿尔茨海默病和威尔逊病患者血清中游离铜离子的配体化合物。