4-trifluoromethoxycinnamic acid | 783-13-1

• 物质功能分类: 香精与香料 - 合成香料 - 芳香肉桂酸、酯及衍生物
• 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
• 英文名称: 4-trifluoromethoxycinnamic acid
• 英文别名: p-trifluoromethoxycinnamic acid；3-(4-trifluoromethoxyphenyl)-2-propenoic acid；3-(4-trifluoromethoxy-phenyl)-acrylic acid；3-(4-trifluoromethoxyphenyl)acrylic acid；4-Trifluormethoxy-zimtsaeure；2-Propenoic acid, 3-[4-(trifluoromethoxy)phenyl]-；3-[4-(trifluoromethoxy)phenyl]prop-2-enoic acid
• CAS: 783-13-1
• 化学式: C₁₀H₇F₃O₃
• mdl: MFCD00066338
• 分子量: 232.159
• InChiKey: RNYVTJANWYBGPW-UHFFFAOYSA-N

物化性质

• 熔点：
  178 °C
• 沸点：
  296.6±35.0 °C(Predicted)
• 密度：
  1.403±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S22,S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2918990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温且干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-[4-(Trifluoromethoxy)phenyl]acrylic acid
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: 3-[4-(Trifluoromethoxy)phenyl]acrylic acid
CAS number: 783-13-1

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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: C10H7F3O3
Molecular weight: 232.2

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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, hydrogen fluoride.

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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

制备方法与用途

化学性质：类白色固体

反应信息

• 作为反应物：
  描述：

  4-trifluoromethoxycinnamic acid 在 双氧水 、 vanadia 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以91%的产率得到4-三氟甲氧基苯甲酸
  参考文献：
  名称：

  氧化钒 (V) 催化过氧化氢对肉桂酸中 C-C 双键的氧化裂解

  摘要：

  我们开发了一种廉价、绿色、温和、环保的方法，以 30% 的过氧化氢水溶液为氧化剂，氧化钒（V）为催化剂，选择性裂解碳-碳双键。肉桂酸衍生物1的氧化裂解选择性取决于取代基和使用的溶剂（DME – MeOCH 2 CH 2 OMe、T​​FE – 2,2,2-三氟乙醇或 MeCN）。在 DME 中，对羟基衍生物选择性地转化为苯甲醛衍生物2，在 TFE 中，氧化裂解导致形成苯醌衍生物4，而在 MeCN 中，肉桂酸衍生物选择性地转化为苯甲酸衍生物3。阿魏酸1a以 91% 的克级分离产率定量和选择性地转化为香草醛2a。二聚二呋喃二酮1a'作为中间体被分离出来，通过原位ATR-IR光谱证实了这一点，而没有观察到二醇或环氧化物的形成。类似的苯乙烯衍生物 4-乙烯基愈创木酚1e也被选择性地转化为香草醛2a或 2-甲氧基醌4a在高产。计算了不同方法阿魏酸转化为香草醛的绿色指标，并与我们的方法进行了比较，表明我们的方法具有更好的环境参数。

  DOI：

  10.1039/d1gc04416h
• 作为产物：
  描述：

  对三氟甲氧基苯甲醛 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 4-trifluoromethoxycinnamic acid
  参考文献：
  名称：

  手性环戊二烯基铱（III）配合物可促进对映选择性环化异构化，生成熔融环丙烷

  摘要：

  环戊二烯基（Cp）基团是许多在催化中应用的过渡金属配合物的重要配体。手性环戊二烯基配体（Cp x）的可用性落后于其他配体类别，因此妨碍了对映选择性过程的研究。我们报告了配备手性Cp支架的手性Cp x Ir III复合物的库。强大的络合程序可为Cp x Ir III络合物可靠地提供可调节的抗衡离子。在概念验证的应用中，含碘化物对烯炔的环异构化反应具有很高的选择性。脱氢哌啶稠合的环丙烷产物以良好的产率和对映选择性形成。

  DOI：

  10.1002/anie.201506483

文献信息

• Deoxygenative trifluoromethylthiolation of carboxylic acids
  作者：Runze Mao、Srikrishna Bera、Alexis Cheseaux、Xile Hu

  DOI：10.1039/c9sc03396c

  日期：——

  Here we describe a deoxygenative trifluoromethylthiolation method that yields trifluoromethyl thioesters from readily available carboxylic acids. The method is built upon an "umpolung" strategy where triphenylphosphine is used to first activate an electrophilic trifluoromethylthiolating reagent and then serves as an oxygen acceptor for the deoxygenation. The method is mild, efficient, broad-scope,

  在这里，我们描述了一种脱氧三氟甲基硫醇化方法，该方法从容易获得的羧酸中产生三氟甲基硫酯。该方法基于“umpolung”策略，其中三苯基膦首先用于激活亲电三氟甲基硫醇化试剂，然后用作脱氧的氧受体。该方法温和、高效、适用范围广、耐受性好。它可用于许多含有羧酸基团的天然产物和药物分子的后期功能化。三氟甲基硫酯可以通过 Pd 催化的脱羰基化转化为三氟甲基硫醚。
• Prodrugs of N-dicarboximide derivatives of the rat selective toxicant norbormide
  作者：David Rennison、Olivia Laita、Daniel Conole、Morgan Jay-Smith、Jan Knauf、Sergio Bova、Maurizio Cavalli、Brian Hopkins、Darwin S. Linthicum、Margaret A. Brimble

  DOI：10.1016/j.bmc.2013.06.071

  日期：2013.9

  Norbormide [5-(α-hydroxy-α-2-pyridylbenzyl)-7-(α-2-pyridylbenzylidene)-5-norbornene-2,3-dicarboximide] (NRB), an existing but infrequently used rodenticide, is known to be uniquely toxic to rats but relatively harmless to other rodents and mammals. However, one major drawback of NRB as a viable rodenticide relates to an evolutionary aversion developed by the rat leading to sub-lethal dosing due to

  已知存在但很少使用的杀虫剂降冰片[5-（α-羟基-α-2-吡啶基苄基）-7-（α-2-吡啶基苄基）-5-降冰片烯-2,3-二甲酰亚胺]（NRB）对大鼠有独特的毒性，但对其他啮齿动物和哺乳动物则无害。然而，作为一种有效的灭鼠剂，NRB的一个主要缺点与大鼠产生的进化厌恶有关，这是由于其令人不快的“味觉”或起效迅速而导致亚致死剂量的。为了“掩盖”这种急性反应，准备了一系列NRB衍生的前药。描述了它们的合成和生物学评估（体外血管收缩活性，体外水解和酶稳定性以及体内致死性/适口性）。前药2在症状发作方面表现出最有前途的表现，随后被证明对大鼠而言更可口。此外，在一项选择试验中发现前药25被大鼠广泛接受，导致高死亡率。
• Visible-Light Photocatalytic Decarboxylation of α,β-Unsaturated Carboxylic Acids: Facile Access to Stereoselective Difluoromethylated Styrenes in Batch and Flow
  作者：Xiao-Jing Wei、Wout Boon、Volker Hessel、Timothy Noël

  DOI：10.1021/acscatal.7b03019

  日期：2017.10.6

  development of synthetic methodologies which provide access to both stereoisomers of α,β-disubstituted olefins is a challenging undertaking. Herein, we describe the development of an operationally simple and stereoselective synthesis of difluoromethylated styrenes via a visible-light photocatalytic decarboxylation strategy using fac-Ir(ppy)3 as the photocatalyst. Meta- and para-substituted cinnamic acids provide

  能够获得α，β-二取代的烯烃的两种立体异构体的合成方法的发展是一项艰巨的任务。在这里，我们描述了通过使用fac -Ir（ppy）3作为光催化剂的可见光光催化脱羧策略，开发一种操作简单且立体选择性的二氟甲基化苯乙烯合成方法。间位和对位取代的肉桂酸可提供预期的E-异构体。相反，邻位肉桂酸选择性地产生不稳定的Z产物，而E-异构体可以通过连续流处理通过精确控制反应时间来获得。此外，我们的方案适用于芳基丙酸的脱羧二氟甲基化。
• Nickel-Catalyzed Decarboxylative Difluoroalkylation of α,β-Unsaturated Carboxylic Acids
  作者：Gang Li、Tao Wang、Fan Fei、Yi-Ming Su、Yan Li、Quan Lan、Xi-Sheng Wang

  DOI：10.1002/anie.201511321

  日期：2016.3.1

  The first example of nickel‐catalyzed decarboxylative fluoroalkylation of α,β‐unsaturated carboxylic acids has been developed with commonly available fluoroalkyl halides. This novel transformation has demonstrated broad substrate scope, excellent functional‐group tolerance, mild reaction conditions, and excellent stereoselectivity. Mechanistic investigations indicate that a fluoroalkyl radical is involved

  用常见的氟代烷基卤化物开发了镍催化α，β-不饱和羧酸的脱羧氟代烷基化的第一个例子。这种新颖的转化证明了广泛的底物范围，出色的官能团耐受性，温和的反应条件和出色的立体选择性。机理研究表明，氟烷基参与了催化循环。
• Design and optimization of quinazoline derivatives as melanin concentrating hormone receptor 1 (MCHR1) antagonists: Part 2
  作者：Sanjita Sasmal、D. Balasubrahmanyam、Hariprasada R. Kanna Reddy、Gade Balaji、Gujjary Srinivas、Srisailam Cheera、Chandrasekhar Abbineni、Pradip K. Sasmal、Ish Khanna、V.J. Sebastian、Vikram P. Jadhav、Manvendra P. Singh、Rashmi Talwar、J. Suresh、Dhanya Shashikumar、K. Harinder Reddy、V. Sihorkar、Thomas M. Frimurer、Øystein Rist、Lisbeth Elster、Thomas Högberg

  DOI：10.1016/j.bmcl.2012.03.049

  日期：2012.5

  Melanin concentrating hormone receptor 1 (MCHR1) antagonists have potential for the treatment of obesity and several CNS disorders. In the preceding article, we have described a novel series of quinazolines as MCHR1 antagonists and demonstrated in vivo proof of principle with an early lead. Herein we describe the detailed SAR and SPR studies to identify an optimized lead candidate having good efficacy in

  黑色素浓缩激素受体 1 (MCHR1) 拮抗剂具有治疗肥胖和多种中枢神经系统疾病的潜力。在上一篇文章中，我们描述了一系列新型喹唑啉作为 MCHR1 拮抗剂，并通过早期先导证明了体内原理证明。在此，我们描述了详细的 SAR 和 SPR 研究，以确定在亚慢性 DIO 模型中具有良好疗效且具有良好心血管安全窗口的优化先导候选药物。