乙酸1-(三氟甲基)乙烯酯 | 2247-91-8

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 乙酸1-(三氟甲基)乙烯酯
• 中文别名: Α-(三氟甲基)乙酸乙烯酯；1-(三氟甲基)乙烯基乙酸酯
• 英文名称: 1-(trifluoromethyl)vinyl acetate
• 英文别名: 3,3,3-trifluoroprop-1-en-2-yl acetate；1,1,1-trifluoro-2-(acetyloxy)-2-propene
• CAS: 2247-91-8
• 化学式: C₅H₅F₃O₂
• mdl: MFCD00040844
• 分子量: 154.089
• InChiKey: VOKGSDIHTCTXDS-UHFFFAOYSA-N

物化性质

• 沸点：
  86 °C
• 密度：
  1.21
• 闪点：
  2 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• TSCA：
  T
• 危险等级：
  3
• 危险品标志：
  Xn,F
• 安全说明：
  S16,S26,S36,S36/37/39
• 危险类别码：
  R36/37/38,R11
• 危险品运输编号：
  UN3272
• 海关编码：
  2915390090
• 包装等级：
  II
• 危险类别：
  3
• 储存条件：
  0-6°C

SDS

Name:	1-(Trifluoromethyl)ethenyl Acetate 99% Material Safety Data Sheet
Synonym:	None
CAS:	2247-91-8

Section 1 - Chemical Product MSDS Name:1-(Trifluoromethyl)ethenyl Acetate 99% Material Safety Data Sheet
Synonym:None

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2247-91-8	1-(Trifluoromethyl)ethenyl Acetate	99%	218-838-2

Hazard Symbols: XN F
Risk Phrases: 11 20/21/22 36/37/38

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Highly flammable. Harmful by inhalation, in contact with skin and if swallowed. Irritating to eyes, respiratory system and skin.Moisture sensitive.Highly flammable.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
Causes gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Vapors may cause dizziness or suffocation.
Chronic:
No information found.

---

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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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. Vapors may form an explosive mixture with air.
Vapors can travel to a source of ignition and flash back. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Use water spray to keep fire-exposed containers cool. Water may be ineffective. Material is lighter than water and a fire may be spread by the use of water. Flammable liquid and vapor. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Will be easily ignited by heat, sparks or flame. Containers may explode if exposed to fire.
Extinguishing Media:
For small fires, use dry chemical, carbon dioxide, water spray or alcohol-resistant foam. Water may be ineffective. Water may spread fire. If water is the only media available, use in flooding amounts.
Do NOT get water inside containers. For large fires, use water spray, fog or alcohol-resistant foam. Do NOT use straight streams of water. Cool containers with flooding quantities of water until well after fire is out.

---

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. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Scoop up with a nonsparking tool, then place into a suitable container for disposal. Remove all sources of ignition. Provide ventilation. Do not get water inside containers.

---

Section 7 - HANDLING and STORAGE
Handling:
Ground and bond containers when transferring material. Use spark-proof tools and explosion proof equipment. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Keep away from heat, sparks and flame. Avoid ingestion and inhalation. Use with adequate ventilation. Do not allow contact with water. Wash clothing before reuse. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames. Keep from contact with moist air and steam.
Storage:
Keep away from heat and flame. Keep away from sources of ignition.
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
Refrigerator/flammables. Store protected from moisture.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 2247-91-8: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: almost colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 86 deg C @ 760.00mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: 2 deg C ( 35.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.2120g/cm3
Molecular Formula: C5H5F3O2
Molecular Weight: 154.09

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, ignition sources, moisture, excess heat, exposure to moist air or water.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported.

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2247-91-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(Trifluoromethyl)ethenyl Acetate - 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
Shipping Name: FLAMMABLE LIQUID, N.O.S.*
Hazard Class: 3
UN Number: 1993
Packing Group: II
IMO
Shipping Name: FLAMMABLE LIQUID, N.O.S.
Hazard Class: 3.2
UN Number: 1993
Packing Group: II
RID/ADR
Shipping Name: FLAMMABLE LIQUID, N.O.S.
Hazard Class: 3
UN Number: 1993
Packing group: II

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN F
Risk Phrases:
R 11 Highly flammable.
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 16 Keep away from sources of ignition - No
smoking.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 28A After contact with skin, wash immediately with
plenty of water.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 2247-91-8: No information available.
Canada
CAS# 2247-91-8 is listed on Canada's NDSL List.
CAS# 2247-91-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2247-91-8 is listed on the TSCA inventory.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  乙酸1-(三氟甲基)乙烯酯 在 (S)-di-1-adamantylphosphino(tert-butylmethylphosphino)methane(1,5-cyclooctadiene)rhodium(I) hexafluoroantimonate 、 氢气 作用下， 以 丙酮 为溶剂， 反应 18.0h， 以90%的产率得到
  参考文献：
  名称：

  庞大的三阻碍象限双膦配体：合成及在铑催化的功能化烯烃的不对称加氢中的应用

  摘要：

  庞大的三阻碍象限双膦配体，二-1-金刚烷基膦基（叔丁基甲基膦基）甲烷，称为BulkyP *，是通过收敛的短路径和无色谱方法合成的。配体是结晶固体，可以很容易地在空气中处理。它的铑（I）配合物在官能化烯烃的不对称氢化中表现出很高的对映选择性和催化活性。

  DOI：

  10.1021/acs.orglett.9b02702
• 作为产物：
  描述：

  三氟氯丙烯 、 溶剂黄146 生成 乙酸1-(三氟甲基)乙烯酯
  参考文献：
  名称：

  HAKACOPA, TORU;MARUTA, JOSIMITI;SUNAGANEH, TAKASI;NEHGISI, AKIRA

  摘要：

  DOI：

文献信息

• Development of a Scalable, Chromatography-Free Synthesis of <i>t</i>-Bu-SMS-Phos and Application to the Synthesis of an Important Chiral CF₃-Alcohol Derivative with High Enantioselectivity Using Rh-Catalyzed Asymmetric Hydrogenation
  作者：Joshua D. Sieber、Sonia Rodriguez、Rogelio Frutos、Frederic Buono、Yongda Zhang、Ning Li、Bo Qu、Ajith Premasiri、Zhibin Li、Zhengxu S. Han、Yibo Xu、Denis Byrne、Nizar Haddad、Jon Lorenz、Nelu Grinberg、Dmitry Kurouski、Heewon Lee、Bikshandarkoil Narayanan、Laurence Nummy、Jason Mulder、Jack D. Brown、Alice Granger、Joe Gao、Mariusz Krawiec、Zeena Williams、Scott Pennino、Jinhua J. Song、Azad Hossain、Nathan K. Yee、Carl Busacca、Frank Roschangar、Yanchao Xin、Zhantong Mao、Xinzhu Zhang、Yaping Hong、Chris H. Senanayake

  DOI：10.1021/acs.joc.7b03022

  日期：2018.2.2

  A chromatography-free, asymmetric synthesis of the C2-symmetric P-chiral diphosphine t-Bu-SMS-Phos was developed using a chiral auxiliary-based approach in five steps from the chiral auxiliary in 36% overall yield. Separtion and recovery of the auxiliary were achieved with good yield (97%) to enable recycling of the chiral auxiliary. An air-stable crystalline form of the final ligand was identified

  C2对称的P-手性二膦酸酯t的无色谱不对称合成-Bu-SMS-Phos使用基于手性助剂的方法开发，距离手性助剂有五个步骤，总收率为36％。以良好的收率（97％）实现了辅助剂的分离和回收，从而可以回收手性辅助剂。鉴定出最终配体的空气稳定的结晶形式，从而能够通过结晶避免色谱分离出最终的配体。应用该合成路线来制备最多4 kg的最终配体。该材料的实用性在三氟甲基乙酸乙烯酯在0.1摩尔％Rh负载量下进行不对称氢化中得到了证明，以优异的收率和对映体过量（98.6％）获得了药物相关手性三氟异丙醇片段的替代物。
• α-Tetrasubstituted Aldehydes through Electronic and Strain-Controlled Branch-Selective Stereoselective Hydroformylation
  作者：Josephine Eshon、Floriana Foarta、Clark R. Landis、Jennifer M. Schomaker

  DOI：10.1021/acs.joc.8b01431

  日期：2018.9.7

  high conversions and yields of tetrasubstituted aldehydes (e.g., 13:1 regioselectivity, 85% ee, and <1% hydrogenation for 1-fluoromethyl acrylate). The scope also encompasses both acyclic 1,1′-disubstituted and trisubstituted, electron-poor alkenes as well as di- and trisubstituted alkenes composed of small rings with exocyclic and endocyclic unsaturation. For example, 1-methylene-β-lactam furnished

  加氢甲酰化利用二氢，一氧化碳和催化剂将烯烃转化为醛。这项工作将手性双二氮杂膦烷（BDP）和双膦酰氨基乙烷连接的铑络合物应用于各种烯烃的加氢甲酰化反应，以生产手性四取代的醛。带有吸电子取代基的1,1'-二取代丙烯酸酯在温和条件下（1摩尔％的催化剂/ BDP配体，150 psig气体，60°C）以高转化率和四取代醛（例如13：1区域选择性）收率进行加氢甲酰化，1-85％ee和小于1％的氢化反应（对于丙烯酸1-氟甲基丙烯酸酯）。该范围还涵盖无环的1,1'-二取代和三取代的贫电子烯烃，以及由具有环外和环内不饱和键的小环组成的二和三取代的烯烃。例如，1-亚甲基-β-内酰胺为四取代的醛提供了98％的选择性和高达83％的ee。值得注意的是，手性三取代双环亚甲基氮丙啶以> 50催化剂周转/小时的速率以> 99％的区域选择性和> 19：1的非对映选择性转化为四取代的醛。HRh（BDP）（CO）非催化反应的N
• Tunable <i>P</i>-Chiral Bisdihydrobenzooxaphosphole Ligands for Enantioselective Hydroformylation
  作者：Renchang Tan、Xin Zheng、Bo Qu、C. Avery Sader、Keith R. Fandrick、Chris H. Senanayake、Xumu Zhang

  DOI：10.1021/acs.orglett.6b01452

  日期：2016.7.15

  Air-stable and tunable chiral bisdihydrobenzooxaphosphole ligands (BIBOPs) were employed in rhodium-catalyzed asymmetric hydroformylation of various terminal olefins with excellent conversions (>99%), moderate-to-excellent enantioselectivities (up to 95:5 er), and branched to linear ratios (b:l) of up to 400.

  空气稳定且可调的手性双二氢苯并恶唑磷配体（BIBOP）用于铑催化的各种末端烯烃的不对称加氢甲酰化反应，具有出色的转化率（> 99％），中等至优异的对映选择性（高达95：5 er），并分支为线性比（b：l）高达400。
• Modular POP Ligands in Rhodium-Mediated Asymmetric Hydrogenation: A Comparative Catalysis Study
  作者：José L. Núñez-Rico、Pablo Etayo、Héctor Fernández-Pérez、Anton Vidal-Ferran

  DOI：10.1002/adsc.201200477

  日期：2012.11.12

  Highly efficient and enantioselective hydrogenation reactions for α-(acylamino)acrylates, itaconic acid derivatives and analogues, α-substituted enol ester derivatives, and α-arylenamides (25 substrates) catalyzed by chiral cationic rhodium complexes of a set of POP ligands have been developed. The catalytic systems derived from these POP ligands provided a straightforward access to enantiomerically

  已开发出由一系列POP配体的手性阳离子铑配合物催化的α-（酰基氨基）丙烯酸酯，衣康酸衍生物和类似物，α-取代的烯醇酯衍生物和α-芳基酰胺（25种底物）的高效和对映选择性氢化反应。衍生自这些POP配体的催化体系可直接获得对映体富集的α-氨基酸，羧酸，胺和醇衍生物，它们是有价值的手性构件。出色的效率（在所有情况下均可完全转化）和极高的对映体过量（94–99％ee不论取代方式如何，对于各种α-取代的烯醇酯衍生物均能达到）。配体（甲氧基或三苯基甲氧基）的R-氧基强烈影响对映选择性和催化活性。金属中心周围较大的空间体积与较高（或相似的）对映选择性有关，但也与较慢的氢化有关。此外，在四个模型底物上观察到的氢化速率遵循相同的趋势，而与配体的R-氧基无关：2-乙酰氨基丙烯酸甲酯>衣康酸二甲酯> 1-苯基乙酸乙烯酯> N-（1-苯基乙烯基）乙酰胺。高达10,000：1的底物与催化剂之比（S / C）足以完全
• Commercially available liquid enol ethers and acetates as gaseous alkyne equivalents in cationic Rh(I)/BINAP-catalyzed chemo- and regioselective formal cross-alkyne cyclotrimerizations
  作者：Hiromi Hara、Masao Hirano、Ken Tanaka

  DOI：10.1016/j.tet.2009.02.047

  日期：2009.6

  A cationic rhodium(I)/BINAP complex catalyzes partial intramolecular [2+2+2] cycloadditions of 1,6- and 1,7-diynes with enol ethers or a ketene acetal giving substituted benzenes in good yields. The same catalyst also catalyzes complete intermolecular [2+2+2] cycloadditions of two different monoynes with enol acetates giving tri- and tetrasubstituted benzenes in good yields with complete regioselectivity

  阳离子铑（I）/ BINAP络合物可催化1,6-和1,7-二炔与烯醇醚或乙烯酮缩醛的部分分子内[2 + 2 + 2]环加成反应，从而以高收率得到取代的苯。相同的催化剂还催化两种不同的单炔与烯醇乙酸酯的完全分子间[2 + 2 + 2]环加成反应，从而以良好的收率和完全的区域选择性得到三和四取代的苯。在当前的铑催化的正式跨炔烃环三聚反应中，可商购的液体烯醇醚和乙酸酯可用作气态炔烃的通用等同物。

表征谱图