4-(4-硝基苯氧基)苯甲腈 | 17076-68-5

• 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-(4-硝基苯氧基)苯甲腈
• 英文名称: 4-(4-nitrophenoxy)benzonitrile
• 英文别名: 4-(3'-nitrophenoxy)benzonitrile；4-cyano-4'-nitro-diphenyl ether；4'-cyano-4-nitrodiphenyl ether；4-cyano-4'-nitro-diphenylether；4-cyanophenoxy-4-nitrobenzene；4-(4-nitro-phenoxy)-benzonitrile
• CAS: 17076-68-5
• 化学式: C₁₃H₈N₂O₃
• mdl: MFCD00443712
• 分子量: 240.218
• InChiKey: YUNRKJHCHMIMLS-UHFFFAOYSA-N

物化性质

• 熔点：
  160 °C
• 沸点：
  391.6±22.0 °C(Predicted)
• 密度：
  1.34±0.1 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：
  78.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2926909090
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(4-Nitrophenoxy)benzonitrile
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-Nitrophenoxy)benzonitrile
CAS number: 17076-68-5

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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: C13H8N2O3
Molecular weight: 240.2

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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-(4-硝基苯氧基)苯甲腈 在 盐酸 、 氢氧化钾 、 铁粉 、 氯化铵 、 sodium nitrite 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.5h， 生成 4-(4-mercapto-phenoxy)-benzonitrile
  参考文献：
  名称：

  Phenoxyphenyl Sulfone N-Formylhydroxylamines (Retrohydroxamates) as Potent, Selective, Orally Bioavailable Matrix Metalloproteinase Inhibitors

  摘要：

  A novel series of sulfone N-formylhydroxylamines (retrohydroxamates) have been investigated as matrix metalloproteinases (MMP) inhibitors. The substitution of the ether linkage of ABT-770 (5) with a sulfone group 13a led to a substantial increase in activity against MMP-9 but was accompanied by a loss of selectivity for inhibition of MMP-2 and -9 over MMP-1 and diminished oral exposure. Replacement of the biphenyl P1' substituent with a phenoxyphenyl group provided compounds that are highly selective for inhibition of MMP-2 and -9 over MMP-1. Optimization of the substituent adjacent to the retrohydroxamate center in this series led to the clinical candidate ABT-518 (6), a highly potent, selective, orally bioavailable MMP inhibitor that has been shown to significantly inhibit tumor growth in animal cancer models.

  DOI：

  10.1021/jm0103920
• 作为产物：
  描述：

  4-乙酰氨基苯酚钾盐 在 铜 盐酸 作用下， 以 乙醇 为溶剂， 生成 4-(4-硝基苯氧基)苯甲腈
  参考文献：
  名称：

  Photoinduced substitution. VIII. Effects of distant substituents on photoinduced aromatic substitution reactions

  摘要：

  DOI：

  10.1021/jo00827a004

文献信息

• Process for manufacturing aryl ethers having different substituents on
  申请人：Institut Francais du Petrole

  公开号：US04596680A1

  公开（公告）日：1986-06-24

  A asymmetrical aryl ether of the formula X--Ar--O--Ar'--Y, wherein Ar and Ar' are each a divalent aromatic radical, X and Y are electron attracting atoms or groups which differ from each other or have different positions on the corresponding aromatic radicals, is produced by heating together, in the presence of a basic catalyst, equimolecular amounts of two aryl carbonates of the formulas: X--Ar--O--CO--O--Ar--X, and Y--Ar'--O--CO--O--Ar'--Y

  一个不对称的芳基醚的化学式为X--Ar--O--Ar'--Y，其中Ar和Ar'各自是二价芳香基团，X和Y是吸电子原子或基团，它们彼此不同或在相应的芳香基团上有不同位置。通过在碱性催化剂存在下加热两个芳基碳酸酯的等摩尔量，即X--Ar--O--CO--O--Ar--X和Y--Ar'--O--CO--O--Ar'--Y的化学式，可以制备这种醚。
• Synthesis of Diaryl Ethers, Diaryl Sulfides, Heteroaryl Ethers and Heteroaryl Sulfides under Microwave Dielectric Heating
  作者：Quanrui Wang、Feng Li、Qingqing Meng、Huansheng Chen、Zhiming Li、Fenggang Tao

  DOI：10.1055/s-2005-865321

  日期：——

  This paper describes the synthesis of diaryl ethers and sulfides by utilizing microwave heating methodology. The methodology is shown to be rapid and efficient for the coupling of phenols or thiophenol with electron-deficient aryl halides through a SNAr reaction. The scope of the protocol can be expanded to six-membered heterocycles bearing a hydroxyl group as well as to the reaction of 2-pyrimidinethiol with mildly activated aryl halides, providing heteroaryl ethers and sulfides, respectively. The advantages of the present method include the wide substrate scope, the obviation of metal catalysts, ease of product isolation, and high purity of products.

  本文描述了利用微波加热技术合成二芳基醚和硫化物的方法。该方法在芳基卤与缺电子酚或苯硫酚的SNAr反应中表现出快速、高效的特点。该方法的应用范围可扩展到含有羟基的六元杂环化合物，以及2-嘧啶硫醇与适度活化的芳基卤的反应，分别得到杂芳基醚和硫化物。目前方法的优势包括广泛的底物适用性、无需金属催化剂、产品分离简便以及高纯度。
• A PEG₁₀₀₀-DAIL[CdCl₃]–toluene temperature-dependent biphasic system that regulates homogeneously catalyzed C–O coupling of organic halides with phenols and alcohols under ligand-free conditions
  作者：Yu Lin Hu、Xiao Yun Ma、Ming Lu

  DOI：10.1139/v10-170

  日期：2011.4

  An efficient, experimentally simple, and convenient procedure for the C–O coupling of organic halides with phenols and alcohols in a PEG₁₀₀₀-DAIL[CdCl₃]–toluene temperature-dependent biphasic system has been developed. The product can be easily isolated by a simple decantation, and the catalytic system can be recycled and reused without loss of catalytic activity.

  在 PEG1000-DAIL[CdCl3]-甲苯温度依赖性双相体系中，开发了一种高效、实验简单且方便的有机卤化物与酚类和醇类的 C-O 偶联过程。通过简单的倾析就可以轻松分离出产物，而且催化系统可以循环和重复使用，不会丧失催化活性。
• Ullmann reaction through ecocatalysis: insights from bioresource and synthetic potential
  作者：Guillaume Clavé、Claire Garel、Cyril Poullain、Brice-Loïc Renard、Tomasz K. Olszewski、Bastien Lange、Mylor Shutcha、Michel-Pierre Faucon、Claude Grison

  DOI：10.1039/c6ra08664k

  日期：——

  We report the elaboration of novel bio-sourced ecocatalysts for the Ullmann coupling reaction. Ecocatalysis is based on the recycling of metals issued from phytoremediation or rehabilitation, and an innovative chemical valorization of the subsequent biomass in the field of catalysis. Here, we describe efficient copper accumulation by plants via phytoextraction and rhizofiltration. These phytotechnologies

  我们报告了新型生物来源的生态催化剂的厄尔曼偶联反应的阐述。生态催化是基于对植物修复或修复过程中释放出的金属的回收利用，以及催化领域后续生物质的创新化学增值。在这里，我们描述了植物通过植物提取和根际过滤的有效铜积累。对这些植物技术进行了重新研究，以证明这些自然资源在绿色化学中具有新的潜力。以所选择的植物中积累的Cu（显着的能力优点II）物种到他们的根或叶，后者可直接用于制备ecocatalysts，称为生态铜®。成型的Eco- Cu®通过ICP-MS，吡啶吸附/解吸的IR研究，TEM，XRD，SM和模型反应对催化剂进行了全面表征，以阐明这些新材料的化学组成和催化活性。生态铜之间观察到特性和活性的显著差异®和常规Cu催化剂。生态铜®是在Ullmann高活性催化剂偶联以较低的Cu量的反应相比于已知的铜催化剂。
• Equilibrium shift in the rhodium-catalyzed acyl transfer reactions
  作者：Mieko Arisawa、Yui Igarashi、Haruki Kobayashi、Toru Yamada、Kentaro Bando、Takuya Ichikawa、Masahiko Yamaguchi

  DOI：10.1016/j.tet.2011.07.031

  日期：2011.10

  enzene. Acid fluorides were converted into acylphosphine sulfides and thioesters using diphosphine disulfides and disulfides/triphenylphosphine, respectively. Aryl esters were obtained from acid fluorides and phenols in the presence of triphenylsilane. Aryl esters, acylphosphine sulfides, and thioesters were also interconverted in the presence of rhodium complexes. These rhodium-catalyzed acyl transfer

  铑/膦配合物催化酰基氟，芳基酯，酰基膦硫化物和硫代酯之间的平衡酰基转移反应。使用合适的共底物来接受杂原子基团将平衡转移到所需的产物上。使用苯甲酰基五氟苯作为氟化物供体，将酰基膦硫化物和芳基酯转化为酰基氟，并使用（4-甲苯基硫代）五氟苯进行硫酯的氟化反应。分别使用二膦二硫化物和二硫化物/三苯基膦将酰氟转化为酰基膦硫化物和硫酯。在三苯基硅烷的存在下，由酰基氟和苯酚获得芳基酯。在铑配合物的存在下，芳基酯，酰基膦硫化物和硫代酯也可以相互转化。这些铑催化的酰基转移反应在中性条件下进行，无需使用酸或碱。羰基铑中间体参与这些反应是由硫代酯和炔烃的羰基硫化反应提示的。