4-甲氧基-[1,1-联苯]-3-羧酸甲酯 | 19617-68-6

• 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-[1,1-联苯]-3-羧酸甲酯
• 英文名称: methyl 4'-methoxy-[1,1'-biphenyl]-3-carboxylate
• 英文别名: Methyl 3-(4-methoxyphenyl)benzoate
• CAS: 19617-68-6
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: RZVVUWOQDFAFGW-UHFFFAOYSA-N

物化性质

• 熔点：
  71-73 °C
• 沸点：
  383.7±35.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2922299090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 3-(4-methoxyphenyl)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: Methyl 3-(4-methoxyphenyl)benzoate
CAS number: 19617-68-6

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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: C15H14O3
Molecular weight: 242.3

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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-甲氧基-[1,1-联苯]-3-羧酸甲酯 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以72.1%的产率得到4’-甲氧基联苯-3-羧酸
  参考文献：
  名称：

  Iridium(iii) complexes with enhanced film amorphism as guests for efficient orange solution-processed single-layer PhOLEDs with low efficiency roll-off

  摘要：

  通过在 2-苯基苯并噻唑配体苯基段的元位上引入苯基取代基，合成了两种新型橙色铱（III）配合物，即 (3Phbt)222Ir(acac) 和 (3OMePhbt)222Ir(acac)。与母体化合物 (bt)222Ir(acac) 相比，这两种化合物的热稳定性和薄膜非晶性都大大增强，因此适合作为高性能溶液处理磷光有机发光二极管（PhOLED）的客体。然而，与(bt)222Ir(acac)相比，含有对位苯基的(4Phbt)222Ir(acac)具有更差的可加工性，这是因为强烈的分子间相互作用会导致自发结晶。以 (3Phbt)222Ir(acac) 和 (3OMePhbt)222Ir(acac) 为客体的单层溶液加工 PhOLED 的峰值电流效率分别为 17.2 cd A-1 和 15.2 cd A-1，最大亮度分别为 28 270 cd m-2 和 27 900 cd m-2。与采用(bt)222Ir(acac)（10.2 cd A-1 和 14 350 cd m-2）和(4Phbt)222Ir(acac)（5.0 cd A-1 和 13 790 cd m-2）作为荧光粉的器件相比，这两种荧光粉的亮度都有很大提高。此外，这些设备在高亮度下的效率衰减非常低。这些目标配合物的电致发光性能之所以大大提高，主要是由于环金属配体的适当取代位点上存在一个刚性苯基，从而提高了热稳定性，减轻了分子间的相互作用，进而增强了薄膜的非结晶性。

  DOI：

  10.1039/c3dt50834j
• 作为产物：
  描述：

  3-[2-(m-iodobenzoyloxy)ethyl]-1-methylimidazolium tetrafluoroborate 在 palladium diacetate 、 氨 、 cesium fluoride 作用下， 以 水 为溶剂， 反应 22.0h， 生成 4-甲氧基-[1,1-联苯]-3-羧酸甲酯
  参考文献：
  名称：

  Exploration of Ionic Liquids as Soluble Supports for Organic Synthesis. Demonstration with a Suzuki Coupling Reaction

  摘要：

  [GRAPHICS]The efficiency of ionic liquid supported synthesis was demonstrated by the Suzuki reaction of ionic liquid supported iodobenzoate compounds with arylboronic acids in aqueous media to give, after cleavage with ammonia/methanol, biaryl products in good yields and high purities, without the need for chromatographic purification.

  DOI：

  10.1021/ol035977y

文献信息

• Decarbonylative Suzuki–Miyaura Cross-Coupling of Aroyl Chlorides
  作者：Tongliang Zhou、Pei-Pei Xie、Chong-Lei Ji、Xin Hong、Michal Szostak

  DOI：10.1021/acs.orglett.0c02250

  日期：2020.8.21

  Herein, we report a catalyst system for Pd-catalyzed decarbonylative Suzuki–Miyaura cross-coupling of aroyl chlorides with boronic acids to furnish biaryls. This strategy is suitable for a broad range of common aroyl chlorides and boronic acids. The synthetic utility is highlighted in the direct late-stage functionalization of pharmaceuticals and natural products capitalizing on the presence of carboxylic

  在此，我们报告了一种用于 Pd 催化的芳酰氯与硼酸脱羰 Suzuki-Miyaura 交叉偶联以提供联芳基化合物的催化剂体系。该策略适用于范围广泛的常见芳酰氯和硼酸。利用羧酸部分的存在，药物和天然产品的直接后期功能化突出了合成效用。广泛的机理和 DFT 研究提供了对反应机理和高脱羰交叉偶联选择性的关键见解。
• Negishi cross-coupling reaction catalyzed by an aliphatic, phosphine based pincer complex of palladium. biaryl formation via cationic pincer-type PdIV intermediates
  作者：Roman Gerber、Olivier Blacque、Christian M. Frech

  DOI：10.1039/c1dt10398a

  日期：——

  The aliphatic, phosphine-based pincer complex [(C10H13-1,3-(CH2P(Cy2)2)Pd(Cl)] (1) is a highly active Negishi catalyst, enable to quantitatively couple various electronically activated, non-activated, deactivated, sterically hindered and functionalized aryl bromides with various diarylzinc reagents within short reaction times and low catalyst loadings. Experimental observations strongly indicate that

  脂族，基于膦的钳形配合物[（C 10 H 13 -1,3-（CH 2 P（Cy 2）2）Pd（Cl）]]（1）是一种高活性Negishi催化剂，能够定量偶联各种电子在短反应时间和低催化剂负载下，用各种二芳基锌试剂活化，未活化，失活，位阻和官能化的芳基溴化物的实验结果强烈表明，分子机理在初始氯离解为1并形成阳离子T-时是有效的成形14E -配合物[（C 10 H ^ 13 -1,3-（CH 2 P（C6 H 11） 2） 2）Pd] +（ B），然后对其进行氧化加成芳基溴（Ar'Br），得到阳离子型五配位芳基溴钳形配合物[（C 10 H 13 -1） ，3-（CH 2 P（Cy 2） 2）Pd（Br）（芳基'）] +（ C），金属中心处于+ IV氧化态，芳基单元相对于脂肪族钳形核处于顺式位置。随后用Zn（芳基） 2进行金属转移，生成了[[C 10 H13 -1,3-（CH 2 P（Cy 2）
• New Nickel-Based Catalytic System with Pincer Pyrrole-Functionalized N-Heterocyclic Carbene as Ligand for Suzuki-Miyaura Cross-Coupling Reactions
  作者：Zhifo Guo、Xiangyang Lei

  DOI：10.1016/j.jorganchem.2021.122068

  日期：2021.11

  catalytic system with Ni(NO3)2·6H2O as the catalyst and a pincer pyrrole-functionalized N-heterocyclic carbene as the ligand was employed in the Suzuki-Miyaura cross-coupling reactions of aryl iodides with arylboronic acids. With 5 mol% catalyst, the catalytic reactions proceeded at 160 °C, giving coupling products in isolated yields of up to 94% in short reaction times (1-4 h). The system worked efficiently

  以Ni(NO 3 ) 2 ·6H 2 O为催化剂，以钳形吡咯官能化的N-杂环卡宾为配体的新型催化体系用于芳基碘与芳基硼酸的Suzuki-Miyaura交叉偶联反应。使用 5 mol% 的催化剂，催化反应在 160 °C 下进行，在短反应时间（1-4 小时）内以高达 94% 的分离产率得到偶联产物。该系统与带有给电子或吸电子基团的芳基碘化物和带有给电子基团的芳基硼酸一起有效地工作。对芳基碘化物和芳基硼​​酸均观察到空间效应。提出该反应经历了 Ni(I)/Ni(III) 催化循环。
• Cobalt-Catalyzed Cross-Coupling Reactions of Arylboronic Esters and Aryl Halides
  作者：Hung A. Duong、Wenqin Wu、Yu-Yuan Teo

  DOI：10.1021/acs.organomet.7b00726

  日期：2017.11.27

  An efficient cobalt catalyst system for the Suzuki–Miyaura cross-coupling reaction of arylboronic esters and aryl halides has been identified. In the presence of cobalt(II)/terpyridine catalyst and potassium methoxide, a diverse array of (hetero)biaryls have been prepared in moderate to excellent yields.

  已经确定了用于芳基硼酸酯和芳基卤化物的Suzuki-Miyaura交叉偶联反应的有效钴催化剂体系。在钴（II）/叔吡啶催化剂和甲醇钾的存在下，已经以中等至极好的收率制备了各种各样的（杂）联芳基。
• Palladium‐catalysed room‐temperature Suzuki–Miyaura coupling in water extract of pomegranate ash, a bio‐derived sustainable and renewable medium
  作者：Rama Moorhy Appa、S. Siva Prasad、Jangam Lakshmidevi、Bandameeda Ramesh Naidu、Manchala Narasimhulu、Katta Venkateswarlu

  DOI：10.1002/aoc.5126

  日期：2019.10

  the first time as a renewable medium for Pd(OAc)2‐catalysed Suzuki–Miyaura cross‐coupling at room temperature. This method offers a simple and sustainable synthesis of biaryls from aryl halides and arylboronic acids under ligand‐ and external base‐free aerobic and ambient conditions. This method has been found effective for both activated and unactivated aryl halides in the production of biaryls with

  源自农业废物的“石榴灰水提取物”（WEPA）首次用作Pd（OAc）2的可再生介质在室温下催化的Suzuki-Miyaura交叉偶联。该方法可在配体和无碱无氧和环境条件下，从芳基卤化物和芳基硼​​酸简单，可持续地合成联芳基。已经发现该方法对联芳烃的生产中活化和未活化的芳基卤化物均有效，产率中等至几乎定量。该方案显示出在芳基卤化物中相同/相似的反应位上具有较高的化学选择性（即，在芳基卤化物的相同卤素或不同卤素上具有选择性）。该方法表现出高的区域选择性，即卤素对芳族核上不同位置上的其他相同卤素的选择性反应性。因此，我们在此披露干净，良性，