ethyl 2'-cyano-[1,1'-biphenyl]-4-carboxylate | 501427-88-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2'-cyano-[1,1'-biphenyl]-4-carboxylate
• 英文别名: Ethyl 4-(2-cyanophenyl)benzoate；ethyl 4-(2-cyanophenyl)benzoate
• CAS: 501427-88-9
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: TVVQJLZUDQSXEA-UHFFFAOYSA-N

物化性质

• 熔点：
  115.0-117.3 °C
• 沸点：
  426.4±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-(2-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-(2-cyanophenyl)benzoate
CAS number: 501427-88-9

---

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：

  ethyl 2'-cyano-[1,1'-biphenyl]-4-carboxylate 在 N-甲基吡咯烷酮 、 sodium azide 、 三乙胺盐酸盐 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 20.0h， 生成 2'-(2H-四唑-5-基)-4-羧酸
  参考文献：
  名称：

  基于片段的cN-II抑制剂的铅优化和生物学评估

  摘要：

  胞质5'-核苷酸酶II（cN-II）抑制剂的开发对于验证cN-II作为逆转对细胞毒性核苷类似物的耐药性的潜在靶点至关重要。我们之前曾报道过基于片段的方法与分子建模相结合，在此，所选的命中片段再次用于基于Ilib-diverse（可通过基于片段的从头设计构建虚拟分子库的软件）的另一种计算方法中生成潜在抑制剂的重点文库。选择了与先前鉴定的化合物有关的分子支架，并产生了一系列新的化合物。19种衍生物中有10种对200μM纯化的重组蛋白表现出50-75％的抑制作用，其中3种衍生物（12、13和18）的K i处于亚毫摩尔范围内（分别为0.84、2.4和0.58 mM）。尽管仅适度的效力，但cN-II抑制剂与细胞毒性嘌呤核苷类似物联合使用对癌细胞具有协同作用。因此，这些衍生物代表一类非核（t）idic cN-II抑制剂，具有克服癌症耐药性的潜在效用，特别是在血液恶性肿瘤中，其中cN-II活性已被描述为重要参数。

  DOI：

  10.1016/j.ejmech.2019.02.040
• 作为产物：
  描述：

  苯佐卡因 在 三苯基膦氯金 作用下， 以 水 、 乙腈 为溶剂， 反应 16.28h， 生成 ethyl 2'-cyano-[1,1'-biphenyl]-4-carboxylate
  参考文献：
  名称：

  金（i）催化的芳基重氮盐与有机锡的交叉偶联反应†

  摘要：

  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。

  DOI：

  10.1039/c8ob00630j

文献信息

• Preparation of Polyfunctional Arylzinc Organometallics in Toluene by Halogen/Zinc Exchange Reactions
  作者：Moritz Balkenhohl、Dorothée S. Ziegler、Alexandre Desaintjean、Leonie J. Bole、Alan R. Kennedy、Eva Hevia、Paul Knochel

  DOI：10.1002/anie.201906898

  日期：2019.9.9

  toluene within 10 min to 5 h through an I/Zn or Br/Zn exchange reaction using bimetallic reagents of the general formula R'2 Zn⋅2 LiOR (R'=sBu, tBu, pTol). Highly sensitive functional groups, such as a triazine, a ketone, an aldehyde, or a nitro group, were tolerated in these exchange reactions, enabling the synthesis of a plethora of functionalized (hetero)arenes after quenching with various electrophiles

  使用通式R'2Zn⋅2LiOR（R'= sBu）的双金属试剂，通过I / Zn或Br / Zn交换反应，在10分钟至5小时内，在甲苯中制备了多种多官能的二芳基和二杂芳基锌物质。 ，tBu，pTol）。在这些交换反应中可以耐受高度敏感的官能团，例如三嗪，酮，醛或硝基，从而可以在用各种亲电试剂淬灭后合成大量官能化的（杂）芳烃。对这些双金属混合物的组成和反应性的深入了解揭示了[R'2 Zn（OR）2 Li2]型高活性二有机二烷氧基锌酸锂的形成。
• Synthesis of unsymmetrical biaryls by electroreductive cobalt-catalyzed cross-coupling of aryl halides
  作者：Paulo Gomes、Hyacinthe Fillon、Corinne Gosmini、Eric Labbé、Jacques Périchon

  DOI：10.1016/s0040-4020(02)01030-x

  日期：2002.10

  consumable anode process allows the electrochemical cross-coupling reaction between various functionalized aromatic halides (iodides, bromides and chlorides) in the presence of cobalt halides as catalyst in a mixed solvent acetonitrile/pyridine (9:1). A great variety of unsymmetrical biaryls are obtained in moderate to excellent yields.

  消耗性阳极工艺允许在混合的乙腈/吡啶（9：1）溶液中，在作为催化剂的卤化钴存在下，各种功能化的芳族卤化物（碘化物，溴化物和氯化物）之间发生电化学交叉偶联反应。以中等至极好的收率获得了许多不对称的联芳基。
• Room-Temperature Palladium-Catalyzed Negishi-Type Coupling: A Combined Experimental and Theoretical Study
  作者：Philippe Ribagnac、Matthias Blug、Jose Villa-Uribe、Xavier-Frédéric Le Goff、Corinne Gosmini、Nicolas Mézailles

  DOI：10.1002/chem.201102369

  日期：2011.12.16

  An air‐stable, bulky electron‐accepting phosphine ligand (phosphabarrelene) allows the easy reduction of a PdII precursor to a Pd0 complex, highly active in room‐temperature Negishi‐type cross‐coupling. DFT calculations show that the use of the electron‐accepting ligand favors both transmetalation (TM) and reductive‐elimination (RE) processes (see scheme; OA=oxidative addition).

  空气稳定，体积大的电子接受膦配体（磷杂环戊烯）可以轻松地将Pd II前体还原为Pd 0复合物，该复合物在室温Negishi型交叉偶联中具有很高的活性。DFT计算表明，使用电子接受配体有利于金属转移（TM）和还原消除（RE）过程（参见方案；OA =氧化加成）。
• Direct Magnesiation of Polyfunctionalized Arenes and Heteroarenes Using (tmp)2Mg⋅2 LiCl
  作者：Giuliano C. Clososki、Christoph J. Rohbogner、Paul Knochel

  DOI：10.1002/anie.200701487

  日期：2007.10.8
• WO2008/87057
  申请人：——

  公开号：——

  公开（公告）日：——