4’-甲基[1,1’-联苯]-4-甲酸甲酯 | 49742-56-5

• 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’-甲基[1,1’-联苯]-4-甲酸甲酯
• 中文别名: 4'-甲基二苯基-4-羧酸甲酯；4'-甲基[1,1'-联苯]-4-甲酸甲酯
• 英文名称: methyl 4-(4-tolyl)benzoate
• 英文别名: methyl 4'-methyl-[1,1'-biphenyl]-4-carboxylate；methyl 4'-methylbiphenyl-4-carboxylate；[1,1'-Biphenyl]-4-carboxylic acid, 4'-methyl-, methyl ester；methyl 4-(4-methylphenyl)benzoate
• CAS: 49742-56-5
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: NSUWJKRQGXBISO-UHFFFAOYSA-N

物化性质

• 熔点：
  115-116 °C
• 沸点：
  350.1±21.0 °C(Predicted)
• 密度：
  1.083

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• TSCA：
  Yes
• 海关编码：
  2916399090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

Name:	Methyl 4 -methylbiphenyl-4-carboxylate Material Safety Data Sheet
Synonym:
CAS:	49742-56-5

Section 1 - Chemical Product MSDS Name:Methyl 4 -methylbiphenyl-4-carboxylate Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
49742-56-5	Methyl 4'-methylbiphenyl-4-carboxylate		256-454-7

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 49742-56-5: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 115 - 116 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C15H14O2
Molecular Weight: 226.27

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 49742-56-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl 4'-methylbiphenyl-4-carboxylate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 49742-56-5: No information available.
Canada
CAS# 49742-56-5 is listed on Canada's NDSL List.
CAS# 49742-56-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 49742-56-5 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4’-甲基[1,1’-联苯]-4-甲酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 生成 4-(溴甲基)-[1,1-联苯]-4-羧酸甲酯
  参考文献：
  名称：

  Correlation of Anti-HIV Activity with Anion Spacing in a Series of Cosalane Analogues with Extended Polycarboxylate Pharmacophores

  摘要：

  Cosalane and its synthetic derivatives inhibit the binding of gp120 to CD4 as well as the fusion of the viral envelope with the cell membrane. The binding of the cosalanes to CD4 is proposed to involve ionic interactions of the negatively charged carboxylates of the ligands with positively charged arginine and lysine amino acid side chains of the protein. To investigate the effect of anion spacing on anti-HIV activity in the cosalane system, a series of cosalane tetracarboxylates was synthesized in which the two proximal and two distal carboxylates are separated by 6-12 atoms. Maximum activity was observed when the proximal and distal carboxylates are separated by 8 atoms. In a series of cosalane amino acid derivatives containing glutamic acid, glycine, aspartic acid, beta -alanine, leucine, and phenylalanine residues, maximum activity was displayed by the di(glutamic acid) analogue. A hypothetical model has been devised for the binding of the cosalane di(glutamic acid) conjugate to CD4. In general, the compounds in this series are more potent against HIV-1(RF) in CEM-SS cells than they are vs HIV-1(IIIB) in MT-4 cells, and they are least potent vs HIV-2(ROD) in MT-4 cells.

  DOI：

  10.1021/jm000290u
• 作为产物：
  描述：

  4-溴苯甲酸乙酯 在 PdCl₂(GLCAphos)2 potassium phosphate 、 三氟化硼乙醚 、 N-[(4-diphenylphosphinophenyl)methyl] D-gluconamide 作用下， 以 水 为溶剂， 反应 16.0h， 生成 4’-甲基[1,1’-联苯]-4-甲酸甲酯
  参考文献：
  名称：

  Palladium-catalyzed biaryl-coupling reaction of arylboronic acids in water using hydrophilic phosphine ligands

  摘要：

  Hydrophilic phosphine ligands possessing a carbohydrate side-chain, such as N-(4-diphenylphosphinophenyl)methyl gluconamide (9), N-[4-(2'-dicyclohexylphosphinobiphenyl)phenylmethyl] gluconamide (10), and N-[4-(2'-di-t-butylphosphinobiphenyl)]phenylmethyl gluconamide (11), were newly synthesized to carry out palladium-catalyzed biaryl coupling of arylboronic acids in a single aqueous medium. The catalyst prepared in situ from Pd(OAc)(2) and 10 exhibited a higher efficiency than that of 9, 11, Ph2P(m-C6H4SO3Na) (TPPMS) or P(m-C6H4SO3Na)(3) (TPPTS) for representative aryl bromides, chlorides, or triflates. The catalyst prepared in situ from Pd(OAc)(2) (0.001 mol%) and 10 (0.002 mol%) achieved 96,000 TON in the reaction of p-tolylboronic acid with 4-bromoacetophenone in water. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00576-8

文献信息

• Metal-free oxidative decarbonylative coupling of aromatic aldehydes with arenes: direct access to biaryls
  作者：Ren-Jin Tang、Qing He、Luo Yang

  DOI：10.1039/c4cc10155c

  日期：——

  A metal-free oxidative decarbonylative coupling of aromatic aldehydes with electron-rich or electron-deficient arenes to produce biaryl compounds was developed. This novel coupling was proposed to proceed via a non-chain radical homolytic aromatic substitution (HAS) type mechanism, based on the substrate scope, ortho-regioselectivity, radical trapping experiments and DFT calculation studies. With the

  开发了芳香醛与富电子或缺电子的芳烃的无金属氧化脱羰基偶联剂，以生产联芳基化合物。基于底物范围，邻位区域选择性，自由基捕获实验和DFT计算研究，提出了通过非链自由基均相芳香族取代（HAS）类型的机理进行这种新型偶联。随着芳香醛和芳烃的现成可用，无金属条件应使这种偶联对于联芳基合成具有吸引力。
• Nanocrystalline Titania-Supported Palladium(0) Nanoparticles for Suzuki-Miyaura Cross-Coupling of Aryl and Heteroaryl Halides
  作者：B. Sreedhar、Divya Yada、P. Surendra Reddy

  DOI：10.1002/adsc.201100012

  日期：2011.10

  The Suzuki cross-coupling reaction of various aryl and heteroaryl halides with arylboronic and heteroarylboronic acids was studied using a titania-supported palladium(0) catalyst at room temperature under air. The conversion and selectivity results obtained for many substrates were excellent and similar to those provided by more active or even homogeneous catalysts. The methodology is similarly effective

  使用二氧化钛负载的钯（0）催化剂在室温下于空气中研究了各种芳基和杂芳基卤化物与芳基硼酸和杂芳基硼酸的Suzuki交叉偶联反应。对于许多底物，获得的转化率和选择性结果极好，与活性更高甚至均相的催化剂所提供的结果相似。使用2-溴-3,4,5-三甲氧基苯甲醛作为偶合伙伴，该方法同样有效，并获得了高收率的产品。此外，已表明其可用于合成三联苯和四联苯。通过简单的过滤从反应中定量回收催化剂，并重复使用多个循环，而活性没有明显损失。
• Micellar catalysis of the Suzuki Miyaura reaction using biogenic Pd nanoparticles from <i>Desulfovibrio alaskensis</i>
  作者：Yuta Era、Jonathan A. Dennis、Stephen Wallace、Louise E. Horsfall

  DOI：10.1039/d1gc02392f

  日期：——

  biogenic palladium nanoparticles generated by the sulfate-reducing bacterium Desulfovibrio alaskensis G20 catalyse the ligand-free Suzuki Miyaura reaction of abiotic substrates. The reaction is highly efficient (>99% yield, 0.5 mol% Pd), occurs under mild conditions (37 °C, aqueous media) and can be accelerated within biocompatible micelles at the cell membrane to yield products containing challenging

  微生物在接触有毒金属离子后会产生金属纳米颗粒 (MNP)。然而，尽管这些生物过程有可能用于可持续回收包括钯在内的关键金属，但生物合成 MNP 的催化活性仍未得到充分探索。在这里，我们报告了由硫酸盐还原菌Desulfovibrio alaskensis产生的生物钯纳米颗粒G20 催化非生物底物的无配体 Suzuki Miyaura 反应。该反应非常高效（产率>99%，Pd 含量为 0.5 mol%），在温和条件下（37 °C，水性介质）发生，并且可以在细胞膜上的生物相容性胶束内加速，产生含有挑战性联芳基键的产物。这项工作强调了厌氧菌的天然代谢过程如何与绿色化学技术相结合，产生高效的催化反应，用于可持续的有机合成。
• Palladium Nanoparticles in Ionic Liquid by Sputter Deposition as Catalysts for Suzuki–Miyaura Coupling in Water
  作者：Yoshiro Oda、Koji Hirano、Kazuki Yoshii、Susumu Kuwabata、Tsukasa Torimoto、Masahiro Miura

  DOI：10.1246/cl.2010.1069

  日期：2010.10.5

  Palladium nanoparticles in an ionic liquid prepared readily by sputter deposition efficiently catalyze the Suzuki–Miyaura coupling of hydrophobic as well as hydrophilic aryl halides in water.

  通过溅射沉积法简易制备的离子液体中的钯纳米颗粒，在水中高效催化疏水和亲水性芳基卤代物的铃木-宫浦偶联反应。
• An imidazolium ionic compound-supported palladium complex as an efficient catalyst for Suzuki–Miyaura reactions in aqueous media
  作者：Yingxiao Zong、Junke Wang、Yubi He、Guoren Yue、Xicun Wang、Yi Pan

  DOI：10.1039/c6ra19850c

  日期：——

  A water soluble and efficient ionic compound-supported palladium complex was prepared. The structure and composition of the complex was characterized by FT-IR, NMR, ICP-OES and mass spectrometry. The complex exhibits high catalytic activity for Suzuki–Miyaura reactions in aqueous media. Moreover, the catalyst shows outstanding stability and reusability, and it can be recovered simply and effectively

  制备了水溶性且有效的离子化合物负载的钯配合物。通过FT-IR，NMR，ICP-OES和质谱对复合物的结构和组成进行了表征。该络合物在水介质中对Suzuki-Miyaura反应具有很高的催化活性。此外，该催化剂显示出优异的稳定性和可重复使用性，并且可以简单有效地回收并重复使用六次而不会降低活性。