3'-硝基-4-联苯醇 | 53059-30-6

• 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-4-联苯醇
• 中文别名: 4-(3-硝基苯基)苯酚
• 英文名称: 4-(3'-nitrophenyl)phenol
• 英文别名: 3'-Nitro-[1,1'-biphenyl]-4-ol；4-(3-nitrophenyl)phenol
• CAS: 53059-30-6
• 化学式: C₁₂H₉NO₃
• 分子量: 215.208
• InChiKey: UNJAJDWFIYUSJV-UHFFFAOYSA-N

物化性质

• 熔点：
  108-108.5 °C(Solv: benzene (71-43-2))
• 沸点：
  386.3±25.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 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：
  66
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2907199090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(3-Nitrophenyl)phenol
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-(3-Nitrophenyl)phenol
CAS number: 53059-30-6

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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: C12H9NO3
Molecular weight: 215.2

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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-4-联苯醇 以 二氯甲烷 、 乙酸乙酯 为溶剂， 以23%的产率得到(2R,3'S,4'S,5'R,6'R)-3',4',5'-tribenzyloxy-6'-(benzyloxymethyl)-6-(3-nitrophenyl)spiro[chromane-2,2'-tetrahydropyran]
  参考文献：
  名称：

  US2014/274930

  摘要：

  公开号：
• 作为产物：
  描述：

  4-碘苯甲醚 在 copper bronze 、 氢溴酸 、 溶剂黄146 作用下， 生成 3'-硝基-4-联苯醇
  参考文献：
  名称：

  Conjugation in the Biphenyl System

  摘要：

  DOI：

  10.1021/ja01651a042

文献信息

• Selective mono-N-methylation of nitroarenes with methanol catalyzed by atomically dispersed NHC-Ir solid assemblies
  作者：Jiaquan Wang、Jiajie Wu、Zhe-Ning Chen、Daheng Wen、Jiangbo Chen、Qingshu Zheng、Xin Xu、Tao Tu

  DOI：10.1016/j.jcat.2020.06.004

  日期：2020.9

  dispersed active Ir(I) centers and the large π-conjugation rings endow the solid catalysts with an exceptionally high activity and selectivity for a broad substrate scope. Such solid NHC-Ir coordination assemblies are robust, which can be easily recovered and reused more than 10 runs without significant loss of their catalytic activity and selectivity. When combined with a subsequent formylation using the same

  制备了一系列基于双-吡咯并咪唑鎓盐的N-杂环卡宾-铱（NHC-Ir）配位组件，并显示出在选择性单N中有效的固体分子催化剂的作用在温和条件下用甲醇对硝基芳烃进行甲基化。原子分散的活性Ir（I）中心和大的π共轭环使固体催化剂在广泛的底物范围内具有异常高的活性和选择性。此类固体NHC-Ir配位组件坚固耐用，可以轻松回收并重复使用10多次以上，而不会显着降低其催化活性和选择性。当与随后在环境条件下使用相同固体催化剂的甲酰化反应相结合时，这种新颖的方法可以以优异的收率提供各种甲酰胺，进一步突显了本发明的固体催化剂对于硝基芳烃有效地多样化为多种功能胺的适用性。
• A General Approach to N-Heterocyclic Carbenes with a Fused Tetracyclic Core: Ligands for Suzuki-Miyaura Cross-Coupling Reaction
  作者：Revannath L. Sutar、Vinod Kumar、Rahul D. Shingare、Shridhar Thorat、Rajesh Gonnade、D. Srinivasa Reddy

  DOI：10.1002/ejoc.201402378

  日期：2014.7

  The synthesis of an N-heterocyclic carbene (NHC) based on a tetracyclic scaffold by using simple, general, and scalable chemistry is disclosed. The developed route is suitable for introducing multiple substitutions on the tetracyclic scaffold. The utility of the present NHC as a ligand in the Suzuki–Miyaura cross-coupling reaction is demonstrated with a low catalyst loading.

  公开了通过使用简单、通用和可扩展的化学合成基于四环支架的 N-杂环卡宾 (NHC)。开发的路线适用于在四环支架上引入多重取代。本发明的 NHC 作为 Suzuki-Miyaura 交叉偶联反应中的配体的实用性在低催化剂负载下得到了证明。
• Pd nanoparticle-silica nanotubes (Pd@SNTs) as an efficient catalyst for Suzuki–Miyaura coupling and sp2 C–H arylation in water
  作者：Ginam Park、Sanghee Lee、Sang Jun Son、Seunghoon Shin

  DOI：10.1039/c3gc41672k

  日期：——

  Silica nanotubes (SNTs) functionalized with Pd-NPs on the inner surface performed as efficient nano-reactors for C–C coupling in water; the nano-confinement offers minimized leaching of Pd and yet efficient mass transfer for Suzuki–Miyaura coupling and C–H arylation of thiazoles in water with very high TON.

  内表面功能化有Pd-NPs的二氧化硅纳米管(SNTs)作为高效的水中C–C耦合纳米反应器；纳米限制提供了最小的Pd浸出现象，同时保证了铃木–宫浦耦合反应和水相中噻唑C–H芳基化反应的高效质量传递,具有非常高的转换数(TON)。
• Design, Synthesis, and Anti-Proliferative Evaluation of [1,1′-biphenyl]-4-ols as Inhibitor of HUVEC Migration and Tube Formation
  作者：Yan Ran、Liang Ma、Xuewei Wang、Jinying Chen、Guangcheng Wang、Aihua Peng、Lijuan Chen

  DOI：10.3390/molecules17078091

  日期：——

  Allylated biphenol neolignans contain a variety of chemopreventive entities that have been used as anti-tumor drug leads. Herein, 37 allylated biphenols were evaluated for anti-proliferative activity by the MTT assay and inhibitory effect on the migration and tube formation of HUVECs featuring anti-angiogenic properties. 3-(2-Methylbut-3-en-2-yl)-3′,5′-bis(trifluoromethyl)-[1,1′-biphenyl]-4-ol (5c) exerted an inhibitory effect on HUVECs compared to honokiol (IC50 = 47.0 vs. 52.6 μM) and showed significant blocking effects on the proliferation of C26, Hela, K562, A549, and HepG2 (IC50 = 15.0, 25.0, 21.2, 29.5, and 13.0 μM, respectively), superior to those of honokiol (IC50 = 65.1, 62.0, 42.0, 75.0, and 55.4 μM, respectively). Importantly, compound 5c inhibited the migration and capillary-like tube formation of HUVECs in vitro.

  烯丙基化联苯新木脂素包含多种化学预防实体，这些实体已被用作抗肿瘤药物的先导化合物。在此，我们评估了37种烯丙基化联苯对细胞增殖活性的抑制作用，以及它们对HUVEC迁移和管形成的抑制效应，这些效应具有抗血管生成特性。3-(2-甲基-3-丁烯-2-基)-3',5'-双(三氟甲基)-[1,1'-联苯]-4-醇（5c）对HUVEC的抑制作用强于细辛醇（IC50 = 47.0 vs. 52.6 μM），并且对C26、Hela、K562、A549和HepG2的增殖有显著阻断作用（IC50分别为15.0、25.0、21.2、29.5和13.0 μM），优于细辛醇的抑制作用（IC50分别为65.1、62.0、42.0、75.0和55.4 μM）。重要的是，化合物5c在体外抑制了HUVEC的迁移和类似毛细血管管的形成。
• Oxidation of 4-arylphenol trimethylsilyl ethers to p-arylquinols using hypervalent iodine(III) reagents
  作者：François-Xavier Felpin

  DOI：10.1016/j.tetlet.2006.11.073

  日期：2007.1

  An efficient synthesis of p-arylquinols by the oxidation of 4-arylphenol trimethylsilyl ethers with phenyliodine(III) diacetate (PIDA) is reported. This protocol greatly improved the yield of p-quinol by minimizing oligomer side products compared to the oxidation of free phenol with hypervalent iodine(III) reagents. The innocuity of phenyliodine(III) diacetate associated with the mild conditions make

  的高效合成p通过4-芳基酚三甲基甲硅烷醚与phenyliodine（III）二乙酸酯（PIDA）报道氧化-arylquinols。与使用高价碘（III）试剂氧化游离苯酚相比，该协议通过最大限度地减少了低聚物副产物，大大提高了对苯二酚的收率。与温和条件相关的苯基乙酸二碘（III）的纯净性使该方法比金属介导的氧化反应更具竞争性。对提出的反应机理进行了讨论，并将其与4-取代苯酚的普遍接受机理进行了比较，以说明产率的提高。