4’-氰基-1,1’-联苯-4-羧酸乙酯 | 89409-89-2

• 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’-氰基-1,1’-联苯-4-羧酸乙酯
• 英文名称: ethyl 4'-cyano-[1,1'-biphenyl]-4-carboxylate
• 英文别名: 4'-cyano-biphenyl-4-carboxylic acid ethyl ester；ethyl 4-(4-cyanophenyl)benzoate
• CAS: 89409-89-2
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: MOBULWWIIMBNQE-UHFFFAOYSA-N

物化性质

• 熔点：
  123-124.5℃
• 沸点：
  414.3±38.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Ethyl 4-(4-cyanophenyl)benzoate
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: Ethyl 4-(4-cyanophenyl)benzoate
CAS number: 89409-89-2

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C16H13NO2
Molecular weight: 251.3

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4’-氰基-1,1’-联苯-4-羧酸乙酯 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 25.0h， 生成
  参考文献：
  名称：

  具有最高互穿度的sql拓扑新发光协调网络的设计与合成

  摘要：

  一种新的纳米长度 ( HL )的 β-二酮配体，其晶体结构显示两个外围腈基之间的距离为 23 Å，已与银 (I) 一起用于组装 2D sql配位网络 (CN)，显示出最高程度的到目前为止，相互渗透（Z ）报告了 7 倍和 8 倍。HL与三氟甲磺酸银和硝酸盐反应可以分离和表征新化合物 [Ag(HL) 2 ](CF 3 SO 3 ) ( 1 ) 和 [Ag(HL) 2 ](NO 3 )·3H 2 O ( 2) 其中只有腈基与四面体银原子配位。X 射线衍射分析表明，两种化合物都存在相似的sql网络，其大菱形窗口（Ag⋯Ag 边缘长度超过 26 Å）允许1和2的Z值分别为 7 和 8。在这两种物质中，不同程度的互穿与配体的构象空间位阻有关，而不是与菱形窗的大小有关，最终是抗衡离子性质的结果。ToposPro 软件的剑桥结构数据库 (CSD) 筛选显示，1和2是独一无二的，据我们所知，具有最高的Z在相互渗透的sql

  DOI：

  10.1039/d2ce00884j
• 作为产物：
  描述：

  对碘苯甲酸乙酯 在 potassium phosphate 、 四(三苯基膦)钯 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 4’-氰基-1,1’-联苯-4-羧酸乙酯
  参考文献：
  名称：

  三（三甲基甲硅烷基）甲硅烷基硼酸酯：用于硼烷基取代和硅烷化反应的新型大体积，空气和水分稳定的甲硅烷基硼酸酯试剂

  摘要：

  通过反应，分别制备了新的笨重的三（三甲基甲硅烷基）甲硅烷基硼酸酯频哪醇和己二醇酯（（TMS）3 Si–B（pin）和（TMS）3 Si–B（hg））。三（三甲基甲硅烷基）甲硅烷基钾与相应的硼亲电子试剂。值得注意的是，这些甲硅烷基硼酸酯在空气和硅胶中表现出很高的稳定性，可用于芳烃卤化物的无过渡金属硼取代，从而以高收率提供所需的硼化产物，并具有出色的B：Si比（高达96％的收率， B / Si = 99/1）。这些新的甲硅烷基硼酸酯还用于与各种芳基卤化物进行的顺序硼酸化/交叉偶联过程，以及用于苯乙烯的碱介导的硅烷化反应。

  DOI：

  10.1021/acs.organomet.7b00476

文献信息

• Gold(<scp>i</scp>)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes
  作者：Manjur O. Akram、Popat S. Shinde、Chetan C. Chintawar、Nitin T. Patil

  DOI：10.1039/c8ob00630j

  日期：——

  Gold(I)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes are described. This redox neutral strategy offers an efficient approach to diverse biaryls, vinyl arenes and arylacetylenes. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the in situ formation of Ph3PAuIR (R = aryl, vinyl and alkynyl) species which is crucial for the activation of aryldiazonium

  描述了金（I）催化的芳基重氮盐与有机锡烷的交叉偶联反应。这种氧化还原中性策略为各种联芳基，乙烯基芳烃和芳基乙炔提供了一种有效的方法。用NMR和ESI-MS监测反应为原位形成Ph 3 PAu I R（R =芳基，乙烯基和炔基）物种提供了有力证据，这对于激活芳基重氮盐至关重要。
• One-Pot Negishi Cross-Coupling Reactions of In Situ Generated Zinc Reagents with Aryl Chlorides, Bromides, and Triflates
  作者：Shohei Sase、Milica Jaric、Albrecht Metzger、Vladimir Malakhov、Paul Knochel

  DOI：10.1021/jo801063c

  日期：2008.9.19

  heteroaryl, alkyl, or benzylic polyfunctional zinc reagents obtained by the addition of zinc and LiCl to the corresponding organic iodides undergo smooth Pd(0)-catalyzed cross-coupling reactions with aryl bromides, chlorides, and triflates in the presence of PEPPSI as a catalyst. This procedure avoids the manipulation of water and air-sensitive organozinc reagents and produces cross-coupling products in high

  通过将锌和LiCl添加到相应的有机碘中获得的原位生成的芳基，杂芳基，烷基或苄基多官能锌试剂，在存在下与芳基溴化物，氯化物和三氟甲磺酸酯进行平滑的Pd（0）催化的交叉偶联反应。 PEPPSI作为催化剂。该程序避免了对水和空气敏感的有机锌试剂的操作，并以高收率生产了交叉偶联产物。
• [EN] ORGANOZINC COMPLEXES AND PROCESSES FOR MAKING AND USING THE SAME<br/>[FR] COMPLEXES D'ORGANOZINC ET PROCÉDÉS POUR LEUR FABRICATION ET LEUR UTILISATION
  申请人：UNIV MUENCHEN L MAXIMILIANS

  公开号：WO2012085168A1

  公开（公告）日：2012-06-28

  Processes for making an organozinc reagents are disclosed comprising reacting (A) organomagnesium or organozinc complexes with (B) at least one coordination compound comprising one or more carboxylate groups and/or alcoholate groups and/or tertiary amine groups, optionally in combination with zinc ions and/or lithium ions and/or halide ions, wherein the halide ions are selected from chloride, bromide and iodide, the organozinc complex comprises an aryl group, a heteroaryl group or a benzyl group when the coordinating compound is a chelating polyamine, and the reaction is conducted in the presence of zinc complexed with at least one coordinating compound when reactant (A) comprises at least one organomagnesium complex. The resulting organozinc reagents may optionally be isolated from solvents to obtain a solid reagent. The reagents may be used for making organic compounds via Negishi cross-coupling reactions or via aldehyde and/or ketone oxidative addition reactions. The organozinc reagents are stable and, due to their high selectivity, permit maintenance of sensitive functional groups such as aldehydes during cross-coupling.

  公开了制备有机锌试剂的方法，包括将（A）有机镁或有机锌配合物与（B）至少一种含有一个或多个羧酸基团和/或醇基团和/或三级胺基团的配位化合物反应，可选地与锌离子和/或锂离子和/或卤离子结合，其中卤离子选自氯离子、溴离子和碘离子，当配位化合物为螯合多胺时，有机锌配合物包括芳基、杂环芳基或苄基，当反应物（A）包含至少一种有机镁配合物时，在存在至少一种配位化合物与锌络合物的情况下进行反应。所得的有机锌试剂可以选择性地从溶剂中分离出来以获得固体试剂。这些试剂可用于通过Negishi交叉偶联反应或通过醛和/或酮氧化加成反应制备有机化合物。有机锌试剂稳定，并且由于其高选择性，允许在交叉偶联过程中保持敏感的官能团，如醛基。
• Nickel-Catalyzed Cross-Coupling of Aryltrimethylammonium Iodides with Organozinc Reagents
  作者：Lan-Gui Xie、Zhong-Xia Wang

  DOI：10.1002/anie.201100683

  日期：2011.5.16

  Broad scope and good tolerance: An efficient cross‐coupling of aryltrimethylammonium iodide salts with aryl‐, methyl‐, and benzylzinc chlorides catalyzed by [Ni(PCy3)2Cl2] has been achieved (see scheme). The reaction involves cleavage of the CN bond and displays broad substrate scope and good functional group tolerance. NMP=N‐methylpyrrolidine.

  广泛的范围和良好的耐受性：[Ni（PCy 3）2 Cl 2 ]催化实现了芳基三甲基碘化碘盐与芳基，甲基和苄基氯化物的有效交叉偶联（参见方案）。该反应涉及CN键的裂解，并显示出较宽的底物范围和良好的官能团耐受性。NMP = N-甲基吡咯烷
• Palladium-Catalyzed Three-Component Coupling of Ynamides
  作者：Hideaki Wakamatsu、Ayano Takahashi、Ayaka Ishii、Youhei Kikuchi、Madoka Sasaki、Yukako Saito、Yoshihiro Natori、Yuichi Yoshimura

  DOI：10.1021/acs.orglett.0c01426

  日期：2020.7.17

  A palladium-catalyzed regioselective three-component coupling of ynamides was developed. The reaction proceeded smoothly to furnish the desired products when carried out at 70 °C in acetonitrile/water with potassium carbonate in the presence of 2.5 mol % Pd2(dba)3·CHCl3 without a ligand. Various iodides and boronic acids were used in this reaction, and a carbon–carbon bond was formed with satisfactory

  开发了钯催化的乙酰胺的区域选择性三组分偶联。当在没有配体的2.5mol％Pd 2（dba）3 ·CHCl 3存在下于70℃在乙腈/水中与碳酸钾一起进行时，反应平稳进行以提供所需的产物。该反应中使用了各种碘化物和硼酸，并且从酰胺中形成了具有令人满意的区域选择性的碳-碳键。