4-甲氧基-4’-氰基联苯 | 58743-77-4

• 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-甲氧基-4’-氰基联苯
• 中文别名: 4-甲氧基-4'-氰基联苯；4-甲氧基[1,1-联苯]-4-甲腈；4-甲氧基-4"-氰基联苯
• 英文名称: 4'-methoxybiphenyl-4-carbonitrile
• 英文别名: 4'-methoxy-1,1'-biphenyl-4-carbonitrile；4′-methoxy[1,1′-biphenyl]-4-carbonitrile；4-cyano-4'-methoxybiphenyl；4'-Methoxy-[1,1'-biphenyl]-4-carbonitrile；4-(4-methoxyphenyl)benzonitrile
• CAS: 58743-77-4
• 化学式: C₁₄H₁₁NO
• mdl: MFCD01003080
• 分子量: 209.247
• InChiKey: RINYLKSNGRLNCU-UHFFFAOYSA-N

物化性质

• 熔点：
  101.5-102.5 °C
• 沸点：
  368.8±35.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 4-(4-Methoxyphenyl)benzonitrile
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 4-(4-Methoxyphenyl)benzonitrile
CAS number: 58743-77-4

---

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: C14H11NO
Molecular weight: 209.2

---

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-甲氧基-4’-氰基联苯 在 二异丁基氢化铝 、 盐酸 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 以82%的产率得到4’-甲氧基联苯-4-甲醛
  参考文献：
  名称：

  [EN] BIPHENYLOXY-ACIDS
  [FR] ACIDES BIPHENYLOXY

  摘要：

  本发明一般涉及取代联苯氧基酸（例如4'-芳基酰胺基联苯基-4(3)-氧基酸和4’-芳基酰胺基甲基联苯基-4(3)-氧基酸）及其使用方法。

  公开号：

  WO2005030702A1
• 作为产物：
  描述：

  4-氰基-4-硝基二苯 在 盐酸 、 硫酸 、 sodium isopropylate 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 溶剂黄146 、 异丙醇 为溶剂， 反应 1.17h， 生成 4-甲氧基-4’-氰基联苯
  参考文献：
  名称：

  Ruolene, Yu. I.; Adomenas, P. V.; Adomenene, O. K., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1192 - 1195

  摘要：

  DOI：

文献信息

• Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation
  作者：L. Reginald Mills、Joshua M. Graham、Purvish Patel、Sophie A. L. Rousseaux

  DOI：10.1021/jacs.9b11208

  日期：2019.12.11

  reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for

  在此，我们报告了一种 Ni 催化的还原偶联，用于从芳基（伪）卤化物和亲电氰化试剂 2-甲基-2-苯基丙二腈 (MPMN) 合成苯甲腈。MPMN 是一种工作台稳定的碳键合亲电子 CN 试剂，在反应条件下不会释放氰化物。可以以良好的收率制备多种与药用相关的苯甲腈。将 NaBr 添加到反应混合物中可以使用更具挑战性的芳基亲电试剂，例如芳基氯化物、甲苯磺酸盐和三氟甲磺酸盐。机理研究表明，溴化钠在促进这些底物的氧化加成方面发挥作用。
• A highly active catalytic system for Suzuki–Miyaura cross-coupling reactions of aryl and heteroaryl chlorides in water
  作者：Shu-Lan Mao、Yue Sun、Guang-Ao Yu、Cui Zhao、Zhi-Jun Han、Jia Yuan、Xiaolei Zhu、Qihua Yang、Sheng-Hua Liu

  DOI：10.1039/c2ob26463c

  日期：——

  An easily available Pd(OAc)2/(2-mesitylindenyl)dicyclohexylphosphine/Me(octyl)3N+Cl−/K3PO4·3H2O catalytic system was developed and it shows high catalytic activity in the Suzuki–Miyaura cross-coupling reaction of a diverse array of aryl and heteroaryl chlorides in water. Notably, this catalytic system also works with ultra-low loading of the catalyst with high turnover numbers.

  容易获得的Pd（OAc）2 /（2-异丁烯基）二环己基膦/ Me的（辛基）3 Ñ +氯- / K 3 PO 4 ·3H 2 ö催化体系被开发，它示出了在芳基和杂芳基氯化物的多样性阵列的Suzuki-Miyaura交叉偶联反应的高催化活性水。值得注意的是，该催化系统还可以在超低负荷下以高周转数运行。
• Air Stable, Sterically Hindered Ferrocenyl Dialkylphosphines for Palladium-Catalyzed C−C, C−N, and C−O Bond-Forming Cross-Couplings
  作者：Noriyasu Kataoka、Quinetta Shelby、James P. Stambuli、John F. Hartwig

  DOI：10.1021/jo025732j

  日期：2002.8.1

  aryl halides coupled with acyclic or cyclic secondary alkyl- and arylamines, with primary alkyl- and arylamines, and with aryl- and primary alkylboronic acids. These last couplings provide the first general procedure for reaction of terminal alkylboronic acids with aryl halides without toxic or expensive bases. The ligand not only generates highly active palladium catalysts, but it is air stable in

  已通过两步合成程序以高收率制备了五苯基二茂铁基二叔丁基膦，并且已研究了由带有该配体的配合物催化的各种交叉偶联过程的范围。该配体为芳基卤化物胺化和Suzuki偶联产生了非常普通的钯催化剂。对于未活化的芳基溴化物或氯化物的胺化，观察到的营业额约为1000。另外，该配体的络合物在温和条件下催化形成选定的芳基醚。反应包括富电子和贫电子的芳基溴化物和氯化物。在含有该配体的催化剂的存在下，这些芳基卤化物与无环或环状仲烷基和芳基胺，伯烷基和芳基胺，以及芳基和伯烷基硼酸偶联。这些最后的偶联为末端烷基硼酸与芳基卤化物的反应提供了第一个通用方法，而没有毒性或昂贵的碱。该配体不仅产生高活性的钯催化剂，而且在溶液和固态中都是空气稳定的。该配体的钯（0）配合物也具有空气稳定性，为固体，仅与溶液中的氧气缓慢反应。
• Catalyst for aromatic C—O, C—N, and C—C bond formation
  申请人：Yale University

  公开号：US06562989B2

  公开（公告）日：2003-05-13

  The present invention is directed to a transition metal catalyst, comprising a Group 8 metal and a ligand having the structure wherein R, R′ and R″ are organic groups having 1-15 carbon atoms, n=1-5, and m=0-4. The present invention is also directed to a method of forming a compound having an aromatic or vinylic carbon-oxygen, carbon-nitrogen, or carbon-carbon bond using the above catalyst. The catalyst and the method of using the catalyst are advantageous in preparation of compounds under mild conditions of approximately room temperature and pressure.

  本发明涉及一种过渡金属催化剂，包括一种第8族金属和具有结构的配体 其中R、R'和R"是具有1-15个碳原子的有机基团，n=1-5，m=0-4。本发明还涉及一种利用上述催化剂形成具有芳香性或乙烯基碳-氧、碳-氮或碳-碳键的化合物的方法。该催化剂和使用该催化剂的方法在大约室温和压力下的温和条件下制备化合物具有优势。
• Decarbonylative Cyanation of Amides by Palladium Catalysis
  作者：Shicheng Shi、Michal Szostak

  DOI：10.1021/acs.orglett.7b01199

  日期：2017.6.16

  Transition-metal-catalyzed cyanation of aryl halides is a process of significant importance in the preparation pharmaceuticals, organic materials and agrochemicals. Here, we demonstrate a palladium-catalyzed decarbonylative cyanation of amides by highly selective carbon–nitrogen bond cleavage for the synthesis of a wide range of aryl nitriles. The utility of this technology is demonstrated by the synthesis

  过渡金属催化的芳基卤化物氰化是制备药物，有机材料和农药的重要过程。在这里，我们通过高选择性的碳-氮键裂解展示了钯催化的酰胺的脱羰氰化氰化物，用于合成各种芳基腈。同位素标记的芳基腈的合成和稳固酰胺的正交交叉偶联反应可建立具有相反极性的交叉偶联合成子，从而证明了该技术的实用性。

表征谱图