1,4-苯二丙烯酸二乙酯 | 17088-28-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 1,4-苯二丙烯酸二乙酯
• 中文别名: 1,4-聚苯二丙烯酸二乙酯
• 英文名称: diethyl 3,3'-(1,4-phenylene)diacrylate
• 英文别名: p-Phenylendiacrylsaeure-diethylester；Diethyl 3,3'-(1,4-phenylene)bisacrylate；ethyl 3-[4-(3-ethoxy-3-oxoprop-1-enyl)phenyl]prop-2-enoate
• CAS: 17088-28-7
• 化学式: C₁₆H₁₈O₄
• 分子量: 274.317
• InChiKey: QYGWZBFQWUBYAT-UHFFFAOYSA-N

物化性质

• 熔点：
  95 °C
• 沸点：
  415.8±33.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 储存条件：
  室温

SDS

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Section I.Chemical Product and Company Identification
Chemical Name 1,4-Phenylenediacrylic Acid Diethyl Ester
Portland OR
Synonym 2-Propenoic Acid, 3,3'-(1,4-Phenylene)bis-, Diethyl Ester
(9 CI)
Chemical Formula C6H4(CH:CHCOOCH2CH3)2
CAS Number 17088-28-7

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Section II. Composition and Information on Ingredients
Toxicology Data
Chemical Name CAS Number Percent (%) TLV/PEL
1,4-Phenylenediacrylic Acid Diethyl Ester 17088-28-7 Not available. Not available. Not available.

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Section III. Hazards Identification
Acute Health Effects No specific information is available in our data base regarding the toxic effects of this material for humans. However,
exposure to any chemical should be kept to a minimum. Skin and eye contact may result in irritation. May be harmful if
inhaled or ingested. Always follow safe industrial hygiene practices and wear proper protective equipment when handling
this compound. Follow safe industrial hygiene practices and always wear proper protective equipment when handling this
compound.
Chronic Health Effects CARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.

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Section IV. First Aid Measures
Check for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for at least 15
Eye Contact
minutes. Get medical attention.
In case of contact, immediately flush skin with plenty of water. Remove contaminated clothing and shoes. Wash clothing
Skin Contact
before reuse. Thoroughly clean shoes before reuse. Get medical attention.
If the victim is not breathing, perform mouth-to-mouth resuscitation. Loosen tight clothing such as a collar, tie, belt or
Inhalation
waistband. If breathing is difficult, oxygen can be administered. Seek medical attention if respiration problems do not
improve.
Ingestion INDUCE VOMITING by sticking finger in throat. Lower the head so that the vomit will not reenter the mouth and throat.
Loosen tight clothing such as a collar, tie, belt or waistband. If the victim is not breathing, perform mouth-to-mouth
resuscitation. Examine the lips and mouth to ascertain whether the tissues are damaged, a possible indication that the toxic
material was ingested; the absence of such signs, however, is not conclusive. SEEK IMMEDIATE MEDICAL ATTENTION in
case of ingestion of a radioactive material.

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Section V. Fire and Explosion Data
Not available.
Auto-Ignition
Flammability May be combustible at high temperature.
Flammable Limits Not available.
Flash Points Not available.
Combustion Products These products are toxic carbon oxides (CO, CO2).
Fire Hazards
Not available.
Risks of explosion of the product in presence of mechanical impact: Not available.
Explosion Hazards
Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting Media
SMALL FIRE: Use DRY chemical powder.
LARGE FIRE: Use water spray, fog or foam. DO NOT use water jet.
and Instructions
Consult with local fire authorities before attempting large scale fire-fighting operations.
Continued on Next Page
1,4-Phenylenediacrylic Acid Diethyl Ester

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Section VI. Accidental Release Measures
Spill Cleanup Use a shovel to put the material into a convenient waste disposal container. Finish cleaning the spill by rinsing any
contaminated surfaces with copious amounts of water. Consult federal, state, and/or local authorities for assistance on
Instructions
disposal.

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Section VII. Handling and Storage
Handling and Storage Keep away from heat. Mechanical exhaust required. When not in use, tightly seal the container and store in a dry, cool
place. Avoid excessive heat and light. Do not breathe dust.
Information
Always store away from incompatible compounds such as oxidizing agents.

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Section VIII. Exposure Controls/Personal Protection
Use process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below recommended
Engineering Controls
exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to airborne contaminants
below the exposure limit.
Splash goggles. Lab coat. Dust respirator. Boots. Gloves. Suggested protective clothing might not be sufficient; consult a
Personal Protection
specialist BEFORE handling this product. Be sure to use a MSHA/NIOSH approved respirator or equivalent.
Exposure Limits Not available.

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Section IX. Physical and Chemical Properties
Solid. Solubility
Physical state @ 20°C Not available.
Not available.
Specific Gravity
274.31
Molecular Weight Partition Coefficient Not available.
Boiling Point Not available. Vapor Pressure Not applicable.
95°C (203°F) Not available.
Melting Point Vapor Density
Not available. Volatility Not available.
Refractive Index
Not available.
Critical Temperature Not available. Odor
Viscosity Not available. Taste Not available.

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Section X. Stability and Reactivity Data
Stability

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This material is stable if stored under proper conditions. (See Section VII for instructions)
Conditions of Instability Avoid excessive heat and light.
Incompatibilities
Reactive with oxidizing agents.

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Section XI. Toxicological Information
Not available.
RTECS Number
Routes of Exposure Eye Contact. Ingestion. inhalation.
Not available.
Toxicity Data
Chronic Toxic Effects CARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.
Acute Toxic Effects No specific information is available in our data base regarding the toxic effects of this material for humans. However,
exposure to any chemical should be kept to a minimum. Skin and eye contact may result in irritation. May be harmful if
inhaled or ingested. Always follow safe industrial hygiene practices and wear proper protective equipment when handling this
compound. Follow safe industrial hygiene practices and always wear proper protective equipment when handling this
compound.

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Section XII. Ecological Information
Not available.
Ecotoxicity
Not available.
Environmental Fate
Continued on Next Page
1,4-Phenylenediacrylic Acid Diethyl Ester

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Section XIII. Disposal Considerations
Waste Disposal Recycle to process, if possible. Consult your local regional authorities. You may be able to dissove or mix material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system. Observe all
federal, state and locl regulations when disposing of the substance.

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Section XIV. Transport Information
Not a DOT controlled material (United States).
DOT Classification
PIN Number Not applicable.
Proper Shipping Name Not applicable.
Packing Group (PG) Not applicable.
DOT Pictograms

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Section XV. Other Regulatory Information and Pictograms
TSCA Chemical Inventory This compound is ON the EPA Toxic Substances Control Act (TSCA) inventory list.
(EPA)
WHMIS Classification On NDSL.
(Canada)
EINECS Number (EEC) 214-150-9
EEC Risk Statements Not available.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1,4-苯二丙烯酸二乙酯 在 sodium tetrahydroborate 、 氯化亚砜 、 nickel(II) chloride hexahydrate 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 1,4-phenylenedipropionyl chloride
  参考文献：
  名称：

  分子和超分子手性对细胞粘附的协同作用

  摘要：

  尽管螺旋纳米纤维结构对细胞粘附有很大影响，但手性分子在这些结构中对细胞行为的作用通常被忽略。螺旋纳米纤维的手性被组装过程中来自同手性1-苯丙氨酸衍生物的亚甲基单元的奇偶效应所颠倒。观察到左手纳米纤维的细胞粘附力增加，而右手纳米纤维的细胞行为也受到微弱影响，即使它们都衍生自1-苯丙氨酸衍生物。还观察到了衍生自d的左手和右手纳米纤维对细胞行为的弱和负面影响。-苯丙氨酸。单个手性分子和螺旋纳米纤维对细胞粘附的影响可能会相互抵消。

  DOI：

  10.1002/anie.201801462
• 作为产物：
  描述：

  对苯二丙烯酸 在 氯化亚砜 作用下， 以 甲苯 为溶剂， 生成 1,4-苯二丙烯酸二乙酯
  参考文献：
  名称：

  分子和超分子手性对细胞粘附的协同作用

  摘要：

  尽管螺旋纳米纤维结构对细胞粘附有很大影响，但手性分子在这些结构中对细胞行为的作用通常被忽略。螺旋纳米纤维的手性被组装过程中来自同手性1-苯丙氨酸衍生物的亚甲基单元的奇偶效应所颠倒。观察到左手纳米纤维的细胞粘附力增加，而右手纳米纤维的细胞行为也受到微弱影响，即使它们都衍生自1-苯丙氨酸衍生物。还观察到了衍生自d的左手和右手纳米纤维对细胞行为的弱和负面影响。-苯丙氨酸。单个手性分子和螺旋纳米纤维对细胞粘附的影响可能会相互抵消。

  DOI：

  10.1002/anie.201801462

文献信息

• Ligand-accelerated non-directed C–H functionalization of arenes
  作者：Peng Wang、Pritha Verma、Guoqin Xia、Jun Shi、Jennifer X. Qiao、Shiwei Tao、Peter T. W. Cheng、Michael A. Poss、Marcus E. Farmer、Kap-Sun Yeung、Jin-Quan Yu

  DOI：10.1038/nature24632

  日期：2017.11

  challenges associated with the lack of sufficiently active palladium catalysts. Currently used palladium catalysts are reactive only with electron-rich arenes, unless an excess of arene is used, which limits synthetic applications. Here we report a 2-pyridone ligand that binds to palladium and accelerates non-directed C–H functionalization with arene as the limiting reagent. This protocol is compatible with

  碳氢键 (C-H) 的定向活化在合成有用反应的发展中很重要，因为通过配位官能团实现了邻近诱导的反应性和选择性。钯催化的非定向 C-H 活化有可能实现进一步有用的反应，因为它可以到达更远的位置并应用于不含适当定向基团的底物；然而，由于缺乏足够活性的钯催化剂，它的发展面临着巨大的挑战。目前使用的钯催化剂仅与富电子芳烃反应，除非使用过量的芳烃，这限制了合成应用。在这里，我们报告了一种 2-吡啶酮配体，它与钯结合并以芳烃为限制剂加速非定向 C-H 功能化。该协议与广泛的芳香底物兼容，我们展示了不能过量使用的高级合成中间体、药物分子和天然产物的直接功能化。我们还开发了 C-H 烯化和羧化方案，证明了我们的方法对其他转化的适用性。这些转化中的位点选择性受空间和电子效应的组合控制，吡啶酮配体增强了空间对选择性的影响，从而为定向 C-H 功能化提供了互补的选择性。该协议与广泛的芳香底物兼容，我们展示了不能
• One-pot selective oxidation/olefination of primary alcohols using TEMPO–BAIB system and stabilized phosphorus ylides
  作者：Jean-Michel Vatèle

  DOI：10.1016/j.tetlet.2005.11.100

  日期：2006.1

  A one-pot process for the synthesis of α,β-unsaturated esters from a variety of alcohols, obtained in good yields and diastereoselectivities, is described. The use of BAIB/TEMPO system at the oxidizing step authorizes the chemoselective homologation of primary alcohols in the presence of secondary ones.

  描述了一种由多种醇合成α，β-不饱和酯的一锅法，该方法具有良好的收率和非对映选择性。在氧化步骤中使用BAIB / TEMPO系统可在存在仲醇的情况下授权伯醇的化学选择性同系物。
• Reactions de wittig-horner et de transesterification en une operation par activation anionique de liaisons C-H et O-H en milieu heterogene carbonate de potassium/alcool
  作者：Z. Mouloungui、R. Elmestour、M. Delmas、A. Gaset

  DOI：10.1016/s0040-4020(01)90785-9

  日期：1992.1

  The Wittig-Horner reaction carried out in various alcohols is accompanied by transesterification of the alkyl radical of the α, β-ethylenic ester formed. The occurrence of these two reactions in the same reaction medium is affected by the behavior of: i) the alcohol (solvent and reagent), ii) potassium carbonate (reagent and catalyst). The propensity for the two reactions to occur was found to depend

  在多种醇中进行的维蒂希-霍纳反应伴随着所形成的α，β-乙烯酯的烷基的酯交换反应。这两个反应在同一反应介质中的发生受到以下行为的影响：i）醇（溶剂和试剂），ii）碳酸钾（试剂和催化剂）。发现发生两个反应的倾向取决于醇的极性。质子醇加快了Wittig-Horner和随后的酯交换反应的速度。尽管使用了非化学计量的碳酸钾，但两个反应都是定量的。原位再生在这些反应条件下，在非质子介质中观察到的固体碱的含量显着提高。为这两个反应提出的机理包括该再生过程。
• A magnetic palladium nickel carbon nanocomposite as a heterogeneous catalyst for the synthesis of distyrylbenzene and biphenyl derivatives
  作者：Habiballah Shafie、Khodabakhsh Niknam

  DOI：10.1039/d1nj01762d

  日期：——

  A magnetic palladium nickel carbon (Fe3O4@Pd@Ni/C) nanocomposite has been synthesized using a simple one-pot procedure via a hydrothermal approach. Ferric nitrate, palladium acetate, and nickel nitrate were dissolved in water together with glucose, and the mixture was heated in an autoclave. The Fe3O4@Pd@Ni/C nanocomposite was characterized via XRD, TEM, FE-SEM, VSM, EDS, and XPS studies. The catalytic

  磁性钯镍碳（Fe 3 O 4 @Pd@Ni/C）纳米复合材料已通过水热法使用简单的一锅法合成。将硝酸铁、醋酸钯和硝酸镍与葡萄糖一起溶解在水中，并将混合物在高压釜中加热。Fe 3 O 4 @Pd@Ni/C 纳米复合材料通过XRD、TEM、FE-SEM、VSM、EDS 和 XPS 研究进行表征。Fe 3 O 4的催化能力研究了@Pd@Ni/C 纳米复合材料用于合成二苯乙烯基苯和 9,10-二苯乙烯基蒽衍生物。该方法显示出明显的优点，如催化剂的可回收性、实验操作简单、收率良好至极好等。
• Stereospecific preparation of ethyl (E) and (Z)-3-aryl-e-phenylpropenoates by heck reaction
  作者：Marcial Moreno-Mañas、Montserrat Pérez、Roser Pleixats

  DOI：10.1016/0040-4039(96)01608-5

  日期：1996.10

  Ethyl cinnamate reacts with several para-substituted aryl iodides under Jeffery-Larock conditions (Pd(OAc)2, NaHCO3, n-Bu4NBr, DMF, Δ) to give ethyl (E)-3-aryl-3-phenylpropenoates as major compounds. The reaction of para-substituted ethyl cinnamates with iodobenzene under analogous conditions affords the corresponding Z isomers. The initially stereodefined alkene formed under Heck conditions undergoes

  肉桂酸乙酯在Jeffery-Larock条件下（Pd（OAc）2，NaHCO 3，n- Bu 4 NBr，DMF，Δ）与几种对位取代的芳基碘化物反应生成乙基（E）-3-芳基-3-苯基丙酸酯主要化合物。对位取代的肉桂酸乙酯与碘代苯在类似条件下的反应得到相应的Z异构体。在Heck条件下形成的最初的立体定义的烯烃经历缓慢的异构化。