methyl 2-(4-(trifluoromethyl)phenyl)acetate | 135325-18-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-(4-(trifluoromethyl)phenyl)acetate
• 英文别名: methyl (4-(trifluoromethyl)phenyl)acetate；(4-(trifluoromethyl)phenyl)acetic acid methyl ester；Methyl 2-[4-(trifluoromethyl)phenyl]acetate
• CAS: 135325-18-7
• 化学式: C₁₀H₉F₃O₂
• mdl: MFCD08669944
• 分子量: 218.175
• InChiKey: ONNMKZXKTBYWFA-UHFFFAOYSA-N

物化性质

• 沸点：
  219.9±35.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2916399090
• 危险性防范说明：
  P264,P270,P301+P312,P330
• 危险性描述：
  H302,H315,H320,H335
• 储存条件：
  应储存在室温、干燥且密封的环境中。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Methyl 2-[4-(trifluoromethyl)phenyl]acetate
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: Methyl 2-[4-(trifluoromethyl)phenyl]acetate
CAS number: 135325-18-7

---

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: C10H9F3O2
Molecular weight: 218.2

---

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.

---

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：

  methyl 2-(4-(trifluoromethyl)phenyl)acetate 在 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 2-(4-(trifluoromethyl)phenyl)propan-1-ol
  参考文献：
  名称：

  在有机铜试剂与γ-芳基α，β-不饱和羰基衍生物的共轭加成中的1,2-不对称诱导

  摘要：

  研究了将有机铜试剂共轭添加到γ-芳基α，β-不饱和羰基衍生物8-14中的非对映选择性。所述顺式得到-diastereoselectivity不论添加8试剂型的，而抗在此外的10-14与RCU和RCU（CN）栗（R =我和丁基）以及得到-diastereoselectivity顺式-通过添加10–14的R 2 CuLi和R 2 Cu（CN）Li 2可以产生选择性。试剂控制的和底物依赖性的非对映选择性是通过两种不同的反应途径来解释的：π络合物的形成或普通的亲核加成。迈克尔受体的还原电势和有机铜试剂的供电子能力控制着反应路径。

  DOI：

  10.1016/s0040-4020(00)00137-x
• 作为产物：
  描述：

  2-羟基-2-(4-(三氟甲基)苯基)乙酸甲酯 在 4-二甲氨基吡啶 、 三乙胺 、 氯磷酸二苯酯 、 双(乙腈)氯化钯(II) 、 sodium tetrahydroborate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 生成 methyl 2-(4-(trifluoromethyl)phenyl)acetate
  参考文献：
  名称：

  钯催化的扁桃酸酯的脱氧

  摘要：

  通过钯催化的扁桃酸酯的脱氧反应，已开发出一种新的合成苯乙酸和酯的方法。

  DOI：

  10.1021/jo8021499

文献信息

• Synthesis of Ketones and Esters from Heteroatom-Functionalized Alkenes by Cobalt-Mediated Hydrogen Atom Transfer
  作者：Xiaoshen Ma、Seth B. Herzon

  DOI：10.1021/acs.joc.6b01709

  日期：2016.10.7

  Cobalt bis(acetylacetonate) is shown to mediate hydrogen atom transfer to a broad range of functionalized alkenes; in situ oxidation of the resulting alkylradical intermediates, followed by hydrolysis, provides expedient access to ketones and esters. By modification of the alcohol solvent, different alkyl ester products may be obtained. The method is compatible with a number of functional groups including

  已显示双（乙酰丙酮酸）钴介导氢原子转移到各种官能化烯烃中。所得烷基自由基中间体的原位氧化，然后水解，可方便地获得酮和酯。通过改性醇溶剂，可以获得不同的烷基酯产物。该方法与许多官能团兼容，包括链烯基卤化物，硫化物，三氟甲磺酸酯和膦酸酯，为乙烯基硅烷的Tamao-Fleming氧化和Arndt-Eistert同系物提供了温和而实用的替代方法。
• Synthesis of γ-Sulfur-Substituted Ketones via Rh(II)/Sc(III) a Cocatalyzed Three-Component Reaction of Diazo Compounds with Thiophenols and Enones
  作者：Guolan Xiao、Chaoqun Ma、Xiang Wu、Dong Xing、Wenhao Hu

  DOI：10.1021/acs.joc.7b03074

  日期：2018.4.20

  A facile method for the synthesis of γ-sulfur-substituted ketones is developed via a Rh(II)/Sc(III) cocatalyzed three-component reaction of diazo compounds with thiophenols and enones. With this method, different γ-sulfur-substituted ketones were obtained in moderate to high yields with good diastereoselectivities.

  通过Rh（II）/ Sc（III）共催化重氮化合物与硫酚和烯酮的三组分反应，开发了一种简便的合成γ-硫取代的酮的方法。用这种方法，可以以中等到高产率获得具有良好非对映选择性的不同的γ-硫取代的酮。
• Room Temperature Coupling of Aryldiazoacetates with Boronic Acids Enhanced by Blue Light Irradiation
  作者：Amanda F. Silva、Marco A. S. Afonso、Rodrigo A. Cormanich、Igor D. Jurberg

  DOI：10.1002/chem.201905812

  日期：2020.5.4

  visible-light-promoted photochemical protocol is reported for the coupling of aryldiazoacetates with boronic acids. This photochemical reaction shows great enhancement compared to the same protocol performed in the absence of light. Except for a few cases, the room temperature coupling in the dark (thermal process) generally does not work. When it does, it is likely to also involve free carbenes as key intermediates

  据报道可见光促进的光化学方案用于芳基重氮乙酸酯与硼酸的偶联。与没有光照的相同方案相比，这种光化学反应显示出极大的增强。除少数情况外，在黑暗（热过程）中的室温耦合通常不起作用。如果这样做的话，很可能还涉及到游离卡宾作为关键中间体。可替代地，光化学反应显示出广泛的范围，可以在空气中进行并且耐受各种各样的官能团。反应进化监测，DFT计算和控制实验已用于评估这种复杂机制的主要方面。具有生物活性的分子阿迪芬，苯那西嗪和阿普生已经被制备为合成应用的实例。
• Macrolide Synthesis through Intramolecular Oxidative Cross-Coupling of Alkenes
  作者：Bing Jiang、Meng Zhao、Shu-Sen Li、Yun-He Xu、Teck-Peng Loh

  DOI：10.1002/anie.201710601

  日期：2018.1.8

  A RhIII‐catalyzed intramolecular oxidative cross‐coupling between double bonds for the synthesis of macrolides is described. Under the optimized reaction conditions, macrocycles containing a diene moiety can be formed in reasonable yields and with excellent chemo‐ and stereoselectivity. This method provides an efficient approach to synthesize macrocyclic compounds containing a 1,3‐conjugated diene

  描述了用于大环内酯合成的双键之间的Rh III催化的分子内氧化交叉偶联。在优化的反应条件下，可以以合理的收率形成具有二烯部分的大环，并具有出色的化学和立体选择性。该方法为合成包含1,3-共轭二烯结构的大环化合物提供了一种有效的方法。
• Enantioselective Construction of Quaternary All-Carbon Centers via Copper-Catalyzed Arylation of Tertiary Carbon-Centered Radicals
  作者：Lianqian Wu、Fei Wang、Pinhong Chen、Guosheng Liu

  DOI：10.1021/jacs.8b13052

  日期：2019.2.6

  An enantioselective copper-catalyzed arylation of tertiary carbon-centered radicals, leading to quaternary all-carbon stereocenters, has been developed herein. The tertiary carbon-centered radicals, including both benzylic and nonbenzylic radicals, were produced by the addition of trifluoromethyl radical to α-substituted acrylamides, and subsequently captured by chiral aryl copper(II) species to give

  本文开发了一种对映选择性铜催化的叔碳中心基团芳基化，导致季全碳立体中心。叔碳中心自由基，包括苄基和非苄基自由基，是通过将三氟甲基自由基加成到 α-取代的丙烯酰胺中产生的，随后被手性芳基铜 (II) 物种捕获，以产生具有优异对映选择性的 C-Ar 键。重要的是，与叔碳自由基相邻的酰基酰胺基 (CONHAr) 基团对于不对称自由基偶联至关重要。该反应本身具有底物范围广、官能团相容性好、条件温和等特点。