4-乙酰基-[1,1-联苯]-4-羧酸乙酯 | 119838-61-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-乙酰基-[1,1-联苯]-4-羧酸乙酯
• 英文名称: ethyl 4'-acetyl-1,1'-biphenyl-4-carboxylate
• 英文别名: ethyl 4'-acetyl-4-biphenylcarboxylate；Ethyl 4-(4-acetylphenyl)benzoate
• CAS: 119838-61-8
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: JPRXSVQGASWWQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2918300090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 4-(4-acetylphenyl)benzoate
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: Ethyl 4-(4-acetylphenyl)benzoate
CAS number: 119838-61-8

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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: C17H16O3
Molecular weight: 268.3

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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.

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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-乙酰基-[1,1-联苯]-4-羧酸乙酯 在 (R)-(3,4,5-trimethoxyphenyl)-MeOBIPHEP 、 TPGS-750-M 、 copper(II) acetate monohydrate 作用下， 以 水 、 甲苯 为溶剂， 反应 1.5h， 以97%的产率得到
  参考文献：
  名称：

  轻质胶束条件下铜催化的芳基/杂芳基酮的不对称还原

  摘要：

  非消旋仲醇的对映选择性合成已通过铜催化的（Cu（OAc）2 ·H 2 O /（R）-3,4,5-MeO-MeO-MePH-BIPHEP）还原芳基/杂芳基在胶束水溶液中实现酮。这种方法学是一种绿色的方案，可使用贱金属催化剂以及廉价，无害且方便的化学计量氢化物源（PMHS）在温和的条件下（0-22°C）获取对映体富集的醇。形成的仲醇产品的收率好至极好，ee值大于90％。

  DOI：

  10.1021/acs.orglett.1c00746
• 作为产物：
  描述：

  4-溴苯甲酸乙酯 在 palladium diacetate 、 cesium fluoride 、 三环己基膦 作用下， 以 neat (no solvent) 为溶剂， 110.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 生成 4-乙酰基-[1,1-联苯]-4-羧酸乙酯
  参考文献：
  名称：

  在无溶剂条件下芳基卤化物的甲氨酰化、Stille 交叉偶联和一锅两步甲氨酰化/Stille 交叉偶联反应

  摘要：

  首次报道了钯催化芳基卤化物、Stille 交叉偶联和一锅两步 stannylation/Stille 交叉偶联 (SSC) 的无溶剂协议。带有受体、供体以及空间要求的取代基的（杂）芳基卤化物以高产率被甲锡烷基化和/或偶联。该反应在空气中由常规的乙酸钯 (II)/PCy3 (Pd(OAc)2/PCy3) 催化，使用可用的碱 CsF，并且不使用高纯度试剂。开发的合成程序用途广泛、稳健且易于扩展。没有溶剂，并消除了芳基锡烷的分离程序，使 SSC 协议简单、步骤经济且高效，用于通过一锅两步程序合成联芳。

  DOI：

  10.1002/ejoc.201701463

文献信息

• Development of a Unique Heterogeneous Palladium Catalyst for the Suzuki-Miyaura Reaction using (Hetero)aryl Chlorides and Chemoselective Hydrogenation
  作者：Tomohiro Ichikawa、Moeko Netsu、Masahiro Mizuno、Tomoteru Mizusaki、Yukio Takagi、Yoshinari Sawama、Yasunari Monguchi、Hironao Sajiki

  DOI：10.1002/adsc.201700156

  日期：2017.7.3

  species. It was also applicable as a chemoselective hydrogenation catalyst, showing inactivity for the hydrogenolysis of tert‐butyldimethylsilyl (TBS) ethers, alkyl benzyl ethers, and benzyl alcohols. The tert‐amines on WA30 acted as moderate catalyst poisons for Pd, resulting in chemoselective hydrogenation. 7% Pd/WA30 was reused for at least five times without any loss of the hydrogenation catalytic

  开发了负载在阴离子交换树脂上的独特多相钯催化剂（7％Pd / WA30），该树脂在聚合物主链上包含N，N-二甲基氨基烷基官能团。7％的Pd / WA30可以顺利催化甚至较低反应性的杂芳基氯化物和的杂酸的铃木-宫浦反应，得到各种（杂）的联芳基因的供电子效应叔上WA30至钯物种-胺。它也可用作化学选择性加氢催化剂，显示出对叔丁基二甲基甲硅烷基（TBS）醚，烷基苄基醚和苄醇的氢解反应的惰性。该叔-WA30上的胺充当Pd的中度催化剂毒物，导致化学选择性氢化。7％Pd / WA30可重复使用至少五次，而不会损失任何氢化催化活性。
• [Pd(Cl)2{P(NC5H10)(C6H11)2}2]-A Highly Effective and Extremely Versatile Palladium-Based Negishi Catalyst that Efficiently and Reliably Operates at Low Catalyst Loadings
  作者：Jeanne L. Bolliger、Christian M. Frech

  DOI：10.1002/chem.201001201

  日期：——

  electronically activated, non‐activated, deactivated, sterically hindered, heterocyclic, and functionalized aryl bromides with various (also heterocyclic) arylzinc reagents, typically within a few minutes at 100 °C in the presence of just 0.01 mol % of catalyst. Aryl bromides containing nitro, nitrile, ether, ester, hydroxy, carbonyl, and carboxyl groups, as well as acetals, lactones, amides, anilines,

  [Pd（Cl）2 P（NC 5 H 10）（C 6 H 11）2 } 2 ]（1）已通过使市售的[Pd（cod）（Cl）2 ]反应定量制备。室温下在几分钟内在N 2中与易于制备的1-（二环己基膦酰基）哌啶在甲苯中的环辛二烯）。综合大楼1已被证明是极佳的Negishi催化剂，能够将各种电子活化，非活化，失活，空间受阻，杂环和官能化的芳基溴化物与各种（也是杂环的）芳基锌试剂定量偶联，通常在几分钟内即可完成。 100°C，仅存在0.01 mol％的催化剂。含有硝基，腈，醚，酯，羟基，羰基和羧基的芳基溴化物，以及缩醛，内酯，酰胺，苯胺，烯烃，羧酸，乙酸，吡啶和嘧啶已被成功用作偶联伙伴。此外，在两个反应伙伴中都可以容忍电子和空间变化。实验观察强烈表明分子机制是有效的。
• Efficient PdCl2-catalyzed Suzuki reactions using simple dicationic imidazolium salts as ligands in aqueous DMF
  作者：Qing Huang、Jiabin Qiu、Limei Li、Guohai Xu、Zhonggao Zhou

  DOI：10.1007/s11243-014-9847-4

  日期：2014.9

  Three new palladium catalysts, prepared via reactions of PdCl2 with readily obtained and inexpensive dicationic imidazolium salts, have been developed for the Suzuki reaction. The pre-catalyst was formed in situ using the imidazolium ligand, base and Pd metal precursor in 1,4-dioxane. This palladium catalyst provides a convenient and general method for the synthesis of biaryls from aryl bromides, activated

  通过 PdCl2 与容易获得且廉价的双阳离子咪唑鎓盐反应制备的三种新型钯催化剂已被开发用于 Suzuki 反应。使用咪唑鎓配体、碱和 Pd 金属前体在 1,4-二恶烷中原位形成预催化剂。这种钯催化剂提供了一种方便和通用的方法，用于在有氧条件下在含水 DMF 中从芳基溴化物、活化的芳基氯化物和含有吸电子取代基和给电子基团的芳基硼酸（19 个实例）合成联芳基化合物（所有 26 个实例）。图形摘要 三种由 PdCl2 制成的新型钯催化剂和容易获得的廉价双阳离子咪唑鎓盐已被开发用于 Suzuki 反应。
• Nanosized Bispyrazole-Based Cryptand-Stabilized Palladium(0) Nanoparticles: A Reusable Heterogeneous Catalyst for the Suzuki–Miyaura Coupling Reaction in Water
  作者：Ashish Verma、Kapil Tomar、Parimal K. Bharadwaj

  DOI：10.1021/acs.inorgchem.8b03015

  日期：2019.1.22

  controlled synthesis and stabilization of ultrafine palladium nanoparticles (Pd NPs) of nearly ∼2 nm size. The as-synthesized Pd NPs were characterized by X-ray photoelectron spectroscopy, transmission electron microscopy, and powder X-ray diffraction. The well-dispersed cryptand-stabilized nanoparticles are found to catalyze the C–C bond-forming Suzuki–Miyaura reaction heterogeneously using water as a green

  合成了具有长刚性腔的大双环穴状配体，其在三个桥的每一个中均包含螯合的双吡唑部分。多个螯合金属结合位点可用于受控合成和稳定近2 nm尺寸的超细钯纳米颗粒（Pd NPs）。通过X射线光电子能谱，透射电子显微镜和粉末X射线衍射对合成后的Pd NP进行表征。发现分散良好的隐链稳定的纳米粒子可使用水作为绿色溶剂，以非均相的方式催化形成C–C键的Suzuki–Miyaura反应。
• Liquid-Assisted Grinding Accelerating: Suzuki–Miyaura Reaction of Aryl Chlorides under High-Speed Ball-Milling Conditions
  作者：Zhi-Jiang Jiang、Zhen-Hua Li、Jing-Bo Yu、Wei-Ke Su

  DOI：10.1021/acs.joc.6b01938

  日期：2016.10.21

  studied using mechanical Suzuki–Miyaura reaction of aryl chlorides as the model reaction. Catalytic systems of Davephos and PCy3 are tested respectively showing strong influences from different liquids. Unexpected improvement of yield over 55% is observed using alcohols as additives, which is explained by in situ formed alkoxides and their participation in oxidative addition. Further expansion of substrates

  使用芳基氯化物的Suzuki-Miyaura机械反应作为模型反应，研究了液体辅助研磨的效果。分别测试了Davephos和PCy 3的催化体系，显示出不同液体的强烈影响。使用醇作为添加剂时，收率意外提高了55％以上，这可通过原位形成的醇盐及其参与氧化加成反应来解释。使用Pd（OAc）2 / PCy 3 / MeOH系统进一步扩展底物，可以以高到高收率获得所需的产物。