4-(三氟甲基)苯甲酸乙酯 | 583-02-8

• 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-(三氟甲基)苯甲酸乙酯
• 中文别名: 4-三氟甲基苯甲酸乙酯
• 英文名称: ethyl 4-(trifluoromethyl)benzoate
• 英文别名: ethyl p-trifluoromethylbenzoate
• CAS: 583-02-8
• 化学式: C₁₀H₉F₃O₂
• mdl: MFCD00013563
• 分子量: 218.175
• InChiKey: ZQDADDSPMCHZPX-UHFFFAOYSA-N

物化性质

• 沸点：
  90 °C
• 密度：
  1.230±0.06 g/cm3(Predicted)
• 闪点：
  78-80°C/5mm
• 稳定性/保质期：
  稳定性与反应性： 要避免的物料：氧化物。 要分解的产品包括一氧化碳、二氧化碳以及氟化氢。

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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

• 危险品标志：
  F
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2916399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  贮存： 将密封器皿密封后，放置于阴凉、干燥处保存。

SDS

Name:	Ethyl 4-(trifluoromethyl)benzoate 97% Material Safety Data Sheet
Synonym:
CAS:	583-02-8

Section 1 - Chemical Product MSDS Name:Ethyl 4-(trifluoromethyl)benzoate 97% Material Safety Data Sheet
Synonym:

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
583-02-8	Ethyl 4-(trifluoromethyl)benzoate	97%	unlisted

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

---

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.

---

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.

---

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.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

---

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.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 583-02-8: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 78 - 80 deg C @5mmHg
Freezing/Melting Point: Not available.
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: C10H9F3O2
Molecular Weight: 218

---

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

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 583-02-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 4-(trifluoromethyl)benzoate - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

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

---

Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

---

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# 583-02-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 583-02-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 583-02-8 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-(三氟甲基)苯甲酸乙酯 在 lithium aluminium tetrahydride 、 氢溴酸 作用下， 以 乙醚 为溶剂， 生成 1-溴-三氟对二甲苯
  参考文献：
  名称：

  消除反应的同位素效应研究。六、2-芳乙基铵离子的双分子消除反应机理

  摘要：

  使用示踪剂和动力学同位素效应技术研究了乙醇中 2-芳基乙基三甲基铵离子与乙醇盐离子的消除反应机理。2-苯基乙基三甲基铵-2,2-d2 溴化物和 2-(对三氟甲基苯基)-乙基三甲基铵-2,2-d2 溴化物均不与溶剂交换，观察到的氮同位素效应分别为 1.3% 和 0.9%。消除了涉及两种盐的自由溶剂化碳负离子中间体的两步过程。当溶剂从乙醇变为水时，观察到氮同位素效应的大小仅发生轻微变化，这也排除了两性离子中间体，该中间体与通过去除 β-氢形成的乙醇分子特异性氢键合乙氧基离子。最后，使用 α- 和 β- 双氘化底物的示踪研究消除了涉及叶立德和卡宾中间体的不太可能的反应途径。结论是2-芳基醚的反应...

  DOI：

  10.1139/v70-017
• 作为产物：
  描述：

  对三氟甲基苯腈 在 硫酸 、 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 4-(三氟甲基)苯甲酸乙酯
  参考文献：
  名称：

  Silver-Catalyzed C–H Trifluoromethylation of Arenes Using Trifluoroacetic Acid as the Trifluoromethylating Reagent

  摘要：

  Direct trifluoromethylation of arenes using TFA as the trifluoromethylating reagent was achieved with Ag as the catalyst. This reaction not only provides a new protocol for aryl CH trifluoromethylation, but the generation of CF3 from TFA may prove useful in other contexts and could potentially be extended to other trifluoromethylation reactions.

  DOI：

  10.1021/ol503189j

文献信息

• A Bifunctional Copper Catalyst Enables Ester Reduction with H₂: Expanding the Reactivity Space of Nucleophilic Copper Hydrides
  作者：Birte M. Zimmermann、Trung Tran Ngoc、Dimitrios-Ioannis Tzaras、Trinadh Kaicharla、Johannes F. Teichert

  DOI：10.1021/jacs.1c09626

  日期：2021.10.13

  activation of esters through hydrogen bonding and formation of nucleophilic copper(I) hydrides from H2, resulting in a catalytic hydride transfer to esters. The reduction step is further facilitated by a proton shuttle mediated by the guanidinium subunit. This bifunctional approach to ester reductions for the first time shifts the reactivity of generally considered “soft” copper(I) hydrides to previously

  采用基于铜 (I)/NHC 配合物和胍有机催化剂的双功能催化剂，促进了以 H 2作为末端还原剂的催化酯还原成醇。这里采用的方法能够通过氢键同时活化酯，并从 H 2形成亲核的氢化铜 (I) ，从而导致氢化物催化转移到酯。由胍亚基介导的质子穿梭进一步促进了还原步骤。这种酯还原的双功能方法首次将通常认为的“软”氢化铜 (I) 的反应性转变为以前不反应的“硬”酯亲电子试剂，并为用催化剂和 H 2替代化学计量还原剂铺平了道路.
• Practical in situ-generation of phosphinite ligands for palladium-catalyzed carbonylation of (hetero)aryl bromides forming esters
  作者：Lin Wang、Helfried Neumann、Anke Spannenberg、Matthias Beller

  DOI：10.1039/c7cc02828h

  日期：——

  An effective method for alkoxycarbonylation of (hetero)aryl bromides is developed in the presence of in situ-generated phosphinite ligands tBu2POR (R = nBu, nPr, Et or Me). For this purpose commercially available tBu2PCl was used as the pre-ligand in the presence of different alcohols. For the first time cross coupling reactions with two alcohols – one generating the ligand, the other used as substrate

  在原位生成的次膦酸酯配体t Bu 2 POR（R = n Bu，n Pr，Et或Me）存在下，开发了一种用于（杂）芳基溴的烷氧羰基化的有效方法。为此目的，在不同醇存在下，将可商购的t Bu 2 PC1用作预配体。首次开发了与两种醇的交叉偶联反应-一种生成配体，另一种用作底物。通过这种方法，可以以更有效的方式进行配体优化，并且可以以良好的产率和选择性获得所需的产物。
• Conversion of Aromatic Amino into Trifluoromethyl Groups through a Sandmeyer­-Type Transformation
  作者：Jianbo Wang、Xi Wang、Yan Xu、Yujing Zhou、Yan Zhang

  DOI：10.1055/s-0033-1338659

  日期：——

  strategy for aromatic trifluoromethylation by converting amino into trifluoromethyl groups via a Sandmeyer-type reaction is reported. The transformation involves diazotization of the aromatic amines with tert-butyl nitrite and hydrochloric acid to form aryldiazonium chlorides, followed by trifluoromethylation with trifluoromethylsilver at low temperature. Various readily available aromatic amines are

  摘要 报道了通过Sandmeyer型反应将氨基转化为三氟甲基的芳香族三氟甲基化的新策略。该转化包括用亚硝酸叔丁酯和盐酸将芳族胺重氮化以形成芳基重氮氯化物，然后在低温下用三氟甲基银进行三氟甲基化。各种容易获得的芳族胺在温和条件下均能平稳转化。 报道了通过Sandmeyer型反应将氨基转化为三氟甲基的芳香族三氟甲基化的新策略。该转化包括用亚硝酸叔丁酯和盐酸将芳族胺重氮化以形成芳基重氮氯化物，然后在低温下用三氟甲基银进行三氟甲基化。各种容易获得的芳族胺在温和条件下均能平稳转化。
• Copper-Promoted Conversion of Aromatic Amines into Trifluoromethylated Arenes: One-Pot Sandmeyer Trifluoromethylation
  作者：Jianquan Hong、Guifu Wang、Lianguang Huo、Changge Zheng

  DOI：10.1002/cjoc.201700311

  日期：2017.11

  A simple copper‐promoted one‐pot Sandmeyer trifluoromethylation of aromatic amines with Langlois’ reagent has been demonstrated. The reaction is performed in mild reaction conditions under an air atmosphere with good substrate scope and functional group compatibility. It provides an alternative and straightforward synthetic approach to access a variety of trifluoromethylated arenes.

  已经证明了使用Langlois试剂进行简单的铜促进的芳香胺的单锅Sandmeyer三氟甲基化。该反应在温和的反应条件下，在具有良好的底物范围和官能团相容性的空气气氛下进行。它提供了一种替代的直接合成方法来访问各种三氟甲基化的芳烃。
• Iron catalysed selective reduction of esters to alcohols
  作者：Sem Raj Tamang、Anthony F. Cozzolino、Michael Findlater

  DOI：10.1039/c8ob02661k

  日期：——

  nature of the anionic complex was probed using EPR and IR experiments and is proposed to involve a dearomatized, radical, ligand scaffold. This complex is an active catalyst for the hydrosilylation of esters to afford alcohols; loadings as low as 1 mol% were employed.

  （dppBIAN）FeCl 2与3当量的n- BuLi反应，得到催化活性的阴离子铁络合物。阴离子配合物的性质已通过EPR和IR实验进行了探索，并被认为涉及一种脱芳香化的自由基配体支架。该络合物是用于酯的氢化硅烷化以提供醇的活性催化剂。使用低至1mol％的负载。

表征谱图