3,5-二(三氟甲基)苯乙烯 | 349-59-7

• 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: 3,5-二(三氟甲基)苯乙烯
• 中文别名: 3,5-双（三氟甲基）苯乙烯；3,5-双(三氟甲基)苯乙烯；3,5-二三氟甲基苯乙烯
• 英文名称: 3,5-bis(trifluoromethyl)styrene
• 英文别名: 1,3-bis(trifluoromethyl)-5-vinylbenzene；3,5-Bis-trifluormethyl-styrol；1-ethenyl-3,5-bis(trifluoromethyl)benzene
• CAS: 349-59-7
• 化学式: C₁₀H₆F₆
• mdl: MFCD00075538
• 分子量: 240.148
• InChiKey: LFICVUCVPKKPFF-UHFFFAOYSA-N

物化性质

• 熔点：
  7-8 °C(lit.)
• 沸点：
  60 °C20 mm Hg(lit.)
• 密度：
  1.334 g/mL at 25 °C(lit.)
• 闪点：
  122 °F

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险等级：
  3
• 危险品标志：
  Xi
• 危险类别码：
  R10
• 危险品运输编号：
  UN 1993 3/PG 3
• WGK Germany：
  3
• 海关编码：
  2903999090
• 包装等级：
  III
• 危险类别：
  3
• 安全说明：
  S16,S26,S36/37/39
• 储存条件：
  储存条件：室温下，请密封保存，并确保环境干燥。

SDS

3,5-Bis(trifluoromethyl)styrene (stabilized with TBC) Revision number: 4
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 3,5-Bis(trifluoromethyl)styrene (stabilized with TBC)

Revision number: 4

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Section 2. HAZARDS IDENTIFICATION
Classification of the GHS
PHYSICAL HAZARDS
Flammable liquids Category 3
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Flammable liquid and vapour
Causes skin irritation
Causes serious eye irritation
Precautionary statements:
[Prevention] Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
Keep container tightly closed.
Use explosion-proof electrical/ventilating/lighting equipment. Take precautionary
measures against ignition by the static discharge and the spark.
Wash hands thoroughly after handling.
Wear protective gloves/eye protection/face protection.
[Response] IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse
skin with water/shower.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.
[Storage] Store in a well-ventilated place. Keep cool.
[Disposal] Dispose of contents/container through a waste management company authorized by
the local government.
Other hazards which do not May cause polimerization.
result in classification
TBC)

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 3,5-Bis(trifluoromethyl)styrene (stabilized with TBC)
Percent: >98.0%(GC)
CAS Number: 349-59-7
Chemical Formula: C10H6F6

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Unsuitable extinguishing Solid streams of water
media:
Specific hazards arising This substance may polimerize explosively when heated or involved in a fire.
from the chemical: Container may explode when heated. Combat fire from a sheltered position.
Take care as it may decompose upon combustion or in high temperatures to
generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Keep containers cool by
spraying with water. Eliminate all ignition sources if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Ensure adequate ventilation. Entry to non-involved personnel should be controlled
emergency procedures: around the leakage area by roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Absorb spilled material in dry sand or inert absorbent before recovering it into a
containment and cleaning covered container. In case of large amount of spillage, contain a spill by bunding.
up: Adhered or collected material should be promptly disposed of, in accordance with
appropriate laws and regulations.
Prevention of secondary Remove all sources of ignition. Fire-extinguishing devices should be prepared in
hazards: case of a fire. Use spark-proof tools and explosion-proof equipment.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent generation of vapor or mist. Keep away from heat/sparks/open flame/hot
surfaces. -No smoking. Take measures to prevent the build up of electrostatic
charge. Use explosion-proof equipment. Wash hands and face thoroughly after
handling.
Use a closed system if possible. Use a ventilation, local exhaust if vapor or aerosol
will be generated.
TBC)

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Section 7. HANDLING AND STORAGE
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool, dark and well-ventilated place.
Store under inert gas.
Store away from incompatible materials such as oxidizing agents.
Air-sensitive
Packaging material: Law is followed.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Install a closed system or local exhaust. Also install safety shower and eye bath.
Engineering controls:
Personal protective equipment
Respiratory protection: Vapor respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Liquid
Physical state (20°C):
Form: clear - slightly cloudy
Color: Colorless - Very pale yellow
No data available
Odor:
pH: No data available
Melting point/freezing point:8°C
Boiling point/range: No data available
50°C
Flash point:
Flammability or explosive
limits:
Lower: No data available
No data available
Upper:
Relative density: 1.35
No data available
Solubility:

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Polymerization may occur under the influences of heat, light or upon contact with
polymelization initiator such as peroxides etc.
Possibility of hazardous No special reactivity has been reported.
reactions:
heat, spark, open flame, static discharge, light
Conditions to avoid:
Incompatible materials: oxidizing agents, strong acids
Hazardous decomposition Carbon monoxide, Carbon dioxide, Hydrogen fluoride
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
No data available
IARC =
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
TBC)

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Section 12. ECOLOGICAL INFORMATION
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobillity in soil
No data available
Log Pow:
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to burn in a chemical
incinerator equipped with an afterburner and scrubber system. Observe all federal, state and local regulations when
disposing of the substance.

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Section 14. TRANSPORT INFORMATION
3: Flammable liquid.
Hazards Class:
UN-No: 1993
Proper shipping name: Flammable liquid, n.o.s.
Packing group: III

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3,5-二(三氟甲基)苯乙烯 在 双(乙腈)氯化钯(II) 、 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II) 、 水 、 异丙醇 、 对苯醌 、 copper dichloride 、 叔丁醇 作用下， 以74%的产率得到2-(3,5-双(三氟甲基)苯基)乙醇
  参考文献：
  名称：

  来自末端烯烃的伯醇：通过三重中继催化的正式反马尔科夫尼科夫水合

  摘要：

  三种催化剂通过引导水以与通常相反的方式攻击碳 - 碳键来产生醇。酒精合成对化学和制药行业至关重要。通过烯烃加入水以形成伯醇（反马尔科夫尼科夫烯烃水合）将是一个广泛有用的反应，但在很大程度上已证明难以捉摸；需要化学计量硼烷和氧化剂的间接硼氢化/氧化顺序是目前最实用的方法。在这里，我们报告了一种使用三重中继催化系统的更直接的方法，该系统将钯催化氧化、酸催化水解和钌催化还原循环结合起来。芳基取代的末端烯烃通过与水的净反应以良好的收率和出色的区域选择性转化为伯醇。

  DOI：

  10.1126/science.1208685
• 作为产物：
  描述：

  3,5-双三氟甲基苯乙炔 在 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、200.0 kPa 条件下， 反应 1.0h， 生成 3,5-二(三氟甲基)苯乙烯
  参考文献：
  名称：

  原位简便合成新型 N 掺杂薄石墨烯层封装 Pd@N/C 催化剂用于炔烃的半氢化

  摘要：

  过渡金属催化的炔烃半加氢已成为最流行的烯烃合成方法之一。具体而言，贵金属 Pd、Rh 和 Ru 基多相催化剂已在学术界和工业界得到广泛研究和应用。但负载型贵金属催化剂在苛刻的反应条件下通常会发生浸出或聚集，导致催化反应活性和稳定性较低。在此，我们报道了氮掺杂石墨烯包封 Pd 催化剂的简便合成及其在炔烃化学选择性半氢化中的应用。通过 X 射线和 TEM 分析证实，石墨烯层对活性 Pd 纳米金属物种起到了“防弹”作用，增强了反应条件下的催化稳定性。优化的准备Pd@N/C催化剂在苯乙炔和其他类型炔烃的半氢化中表现出优异的效率，这些炔具有未官能化或官能化的取代基，包括氢化敏感官能团（NO 2、酯和卤素）。

  DOI：

  10.1016/j.jcat.2021.11.012

文献信息

• Rhenium‐Catalyzed Decarboxylative Tri‐/Difluoromethylation of Styrenes with Fluorinated Carboxylic Acid‐Derived Hypervalent Iodine Reagents
  作者：Yin Wang、Yunhui Yang、Congyang Wang

  DOI：10.1002/cjoc.201900296

  日期：2019.12

  Herein, unprecedented rhenium‐catalyzed decarboxylative oxytri‐/difluoromethylation and Heck‐type trifluoromethylation of styrenes have been developed by using hypervalent iodine(III) reagents derived from cheap, stable, and easy‐handling fluorinated carboxylic acids. Mechanistic studies revealed a radical decarboxylative trifluoromethylation pathway occurring in these reactions.

  在此，通过使用廉价，稳定且易于操作的氟化羧酸衍生的高价碘（III）试剂，开发出了前所未有的苯乙烯催化的de催化脱羧氧基三/二氟甲基化和Heck型三氟甲基化反应。机理研究揭示了在这些反应中发生的自由基脱羧三氟甲基化途径。
• Starting from Styrene: A Unified Protocol for Hydrotrifluoromethylation of Diversified Alkenes
  作者：Yi-Fei Yang、Jin-Hong Lin、Ji-Chang Xiao

  DOI：10.1021/acs.orglett.1c03630

  日期：2021.12.3

  In contrast with unactivated alkenes, the corresponding hydrotrifluoromethylation of styrene has remained challenging due to the strong propensity of styrene for oligomerization and polymerization. On the basis of our newly developed trifluoromethylation reagent, TFSP, herein we present a general method for the hydrotrifluoromethylation of styrene under photoredox catalysis. The substrate scope was

  与未活化的烯烃相比，由于苯乙烯具有强烈的低聚和聚合倾向，相应的苯乙烯氢三氟甲基化仍然具有挑战性。在我们新开发的三氟甲基化试剂 TFSP 的基础上，我们提出了一种在光氧化还原催化下苯乙烯氢三氟甲基化的通用方法。底物范围进一步扩展到未活化的烯烃、丙烯酸酯、丙烯酰胺和乙烯基杂原子取代的烯烃。通过相关的去质子三氟甲基化和三氟甲基三氟乙氧基化反应展示了该方法的可调性。
• Formal hydration of non-activated terminal olefins using tandem catalysts
  作者：Yongsheng Yang、Jiayi Guo、Huimin Ng、Zhiyong Chen、Peili Teo

  DOI：10.1039/c3cc48810a

  日期：——

  The hydration of terminal olefins to secondary alcohols has been achieved using a Pd(II)/Ru(II) catalyst combination with high regioselectivity and yields. Both vinyl arenes and aliphatic olefins can be hydrated easily with the tandem catalyst system using a low catalyst loading of 1 mol%.

  使用Pd(II)/Ru(II)催化剂组合，成功实现了端烯向仲醇的高区域选择性和产率的水合反应。不论是乙烯基芳烃还是脂肪族烯烃，都能在低催化剂负载量（1 mol%）下，利用这种串联催化体系轻松进行水合反应。
• Visible-Light-Driven, Metal-Free Divergent Difunctionalization of Alkenes Using Alkyl Formates
  作者：Ming Zheng、Jing Hou、Le-Wu Zhan、Yan Huang、Ling Chen、Li-Li Hua、Yan Li、Wan-Ying Tang、Bin-Dong Li

  DOI：10.1021/acscatal.0c04332

  日期：2021.1.15

  difunctionalization of alkenes has received considerable attention as an efficient and straightforward way to increase molecular complexity. However, examples of the difunctionalization of alkenes initiated by the intermolecular addition of alkoxycarbonyl radicals providing substituted alkanoates are still rare. Herein, we present the visible light-driven metal-free divergent difunctionalization of alkenes triggered

  在最近几十年中，烯烃的双官能化作为增加分子复杂性的有效而直接的方法受到了广泛的关注。然而，通过分子间加成烷氧基羰基以提供取代的链烷酸酯而引发的烯烃的双官能化的例子仍然很少。在这里，我们介绍了在环境条件下由烷氧基羰基分子间加成引发的可见光驱动的烯烃的无金属发散双官能化。使用烷基甲酸酯作为烷氧羰基自由基的前体，并使用4CzIPN作为光催化剂，可以轻松获得具有高官能团耐受性和高官能度的各种取代链烷酸酯，包括β-烷氧基，β-羟基，β-二甲氧基甲氧基和β-甲酰氧基链烷酸酯。效率。此外，N-烷氧基叠氮盐。
• Palladium-Catalyzed Highly Regio- and Enantioselective Hydroesterification of Aryl Olefins with Phenyl Formate
  作者：Jingfu Li、Wenju Chang、Wenlong Ren、Jie Dai、Yian Shi

  DOI：10.1021/acs.orglett.6b02467

  日期：2016.11.4

  An effective Pd-catalyzed regio- and enantioselective hydroesterification of aryl olefins with phenyl formate is described. A variety of phenyl 2-arylpropanoates can be obtained in good yields with high b/l ratios and ee’s without using toxic CO gas.

  描述了芳基烯烃与甲酸苯基酯的有效的Pd催化的区域和对映选择性加氢酯化。无需使用有毒的CO气体，就可以以高的b / l比和ee以高收率获得各种2-芳基丙酸苯基酯。