4-溴-β,β-二氟苯乙烯 | 84750-93-6

• 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-溴-β,β-二氟苯乙烯
• 中文别名: 4-溴-Beta,Beta-二氟苯乙烯；4-溴-Β,Β-二氟代苯乙烯；1-溴-4-(2,2-二氟乙烯基)苯；4-溴-Β,Β-二氟代苯乙烯(含稳定剂叔丁基邻苯二酚)
• 英文名称: 1,1-difluoro-2-(4-bromophenyl)ethene
• 英文别名: 1-bromo-4-(2,2-difluorovinyl)benzene；1-bromo-4-(2,2-difluoroethenyl)benzene
• CAS: 84750-93-6
• 化学式: C₈H₅BrF₂
• 分子量: 219.029
• InChiKey: LXJISEJYMAHRKE-UHFFFAOYSA-N

物化性质

• 沸点：
  209.8±30.0 °C(Predicted)
• 密度：
  1.57

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2903999090
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险品运输编号：
  3265
• 危险性描述：
  H227,H314
• 储存条件：
  冷藏

SDS

4-Bromo-β,β-difluorostyrene (stabilized with TBC)
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 4-Bromo-β,β-difluorostyrene (stabilized with TBC)

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS
Flammable liquids Category 4
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Serious eye damage/eye irritation Category 2A
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Combustible liquid
Causes skin irritation
Causes serious eye irritation
Precautionary statements:
[Prevention] Keep away from flames and hot surfaces.
Wash hands thoroughly after handling.
Wear protective gloves and eye/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: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.
Store in a well-ventilated place. Keep cool.
[Storage]
[Disposal] Dispose of contents/container through a waste management company authorized by
the local government.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 4-Bromo-β,β-difluorostyrene (stabilized with TBC)
Percent: >98.0%(GC)
CAS Number: 84750-93-6
4-Bromo-β,β-difluorostyrene (stabilized with
TBC)

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
1-Bromo-4-(2,2-difluorovinyl)benzene (stabilized with TBC) , 2-(4-Bromophenyl)-1,1-
Synonyms:
difluoroethylene (stabilized with TBC)
C8H5BrF2
Chemical Formula:

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Section 4. FIRST AID MEASURES
Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Inhalation:
Get medical advice/attention if you feel unwell.
Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
Skin contact:
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Rinse cautiously with water for several minutes. Remove contact lenses, if present
Eye contact:
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.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
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 Take care as it may decompose upon combustion or in high temperatures to
generate poisonous fume.
from the chemical:
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: Remove movable
containers 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 a suitable absorbent (e.g. rag, dry sand, earth, saw-dust).
containment and cleaning In case of large amount of spillage, contain a spill by bunding. Adhered or collected
up: 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 vapour or mist. Keep away from flames and hot surfaces. 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, ventilation.
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 freezer.
Store under inert gas.
Store away from incompatible materials such as oxidizing agents.
4-Bromo-β,β-difluorostyrene (stabilized with
TBC)

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Section 7. HANDLING AND STORAGE
Heat-sensitive, Air-sensitive
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Vapor respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Liquid
Form: Clear
Colour: Very pale yellow - Yellow
Odour: No data available
pH: No data available
Melting point/freezing point:No data available
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: 1.57
Solubility(ies):
[Water] No data available
[Other solvents] No data available

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Open flame
Conditions to avoid:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Hydrogen fluoride, Hydrogen bromide
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:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
No data available
Crustacea:
Algae: No data available
Persistence / degradability: No data available
4-Bromo-β,β-difluorostyrene (stabilized with
TBC)

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Section 12. ECOLOGICAL INFORMATION
No data available
Bioaccumulative
potential(BCF):
Mobility in soil
Log Pow: No data available
No data available
Soil adsorption (Koc):
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
Hazards Class: Does not correspond to the classification standard of the United Nations
Not listed
UN-No:

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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：

  4-溴-β,β-二氟苯乙烯 在 potassium fluoride 、 18-冠醚-6 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以92%的产率得到1-溴-4-(2,2,2-三氟乙基)-苯
  参考文献：
  名称：

  Lee, Chuan-Chen; Lin, Shaw-Tao, Journal of Chemical Research - Part S, 2000, # 3, p. 142 - 144

  摘要：

  DOI：
• 作为产物：
  描述：

  (4-溴苄基)三苯基溴化磷鎓 在 potassium tert-butylate 作用下， 以 对二甲苯 为溶剂， 反应 1.25h， 生成 4-溴-β,β-二氟苯乙烯
  参考文献：
  名称：

  叶立德与二氟卡宾的烯化反应由苄基溴一锅法合成宝石-二氟苯乙烯

  摘要：

  描述了一种由苄基溴合成宝石-二氟苯乙烯的新方法。的三苯基膦与苄基溴，得到鏻盐，相应的鏻盐，以产生磷叶立德，并与二氟卡宾从二氟亚甲基磷酸酯生成鏻内鎓盐的后续烯的脱质子化（PH季铵化3 P + CF 2 CO 2 -可以发生通过脱羧）在一个锅中平稳地进行，以高收率提供最终的宝石-二氟苯乙烯。

  DOI：

  10.1016/j.jfluchem.2015.06.009

文献信息

• Conversion between Difluorocarbene and Difluoromethylene Ylide
  作者：Jian Zheng、Jin-Hong Lin、Ji Cai、Ji-Chang Xiao

  DOI：10.1002/chem.201303248

  日期：2013.11.4

  The interconversion between difluoromethylene ylide and difluorocarbene is described. The difluoromethylene ylide precursor, Ph3P+CF2CO2−, could be turned into an efficient difluorocarbene reagent, whereas the classical difluorocarbene reagents, HCF2Cl and FSO2CF2CO2TMS, could generate highly reactive difluoromethylene ylide. Thus the Wittig difluoro‐olefination and difluorocyclopropanation could be

  描述了二氟亚甲基叶立德和二氟卡宾之间的相互转化。该二氟亚甲基叶立德前体中，Ph 3 P + CF 2 CO 2 - ，也可以变成一个高效的二氟卡宾的试剂，而经典二氟卡宾的试剂，HCF 2 Cl和FSO 2 CF 2 CO 2 TMS，可能会产生高反应性的二氟亚甲基内鎓盐。因此，使用相同的试剂可以选择性地实现Wittig的二氟烯烃化和二氟环丙烷化。另外，从不同卡宾来源获得的叶立德在维蒂希反应中显示出不同的反应性。
• A one-step synthesis of gem-difluoroolefins from alcohols
  作者：Xuan Xiao、Xu Yao、Jiao Yu、Ting Tang、Can Xiao、Jinying Gu、Jin-Hong Lin、Xing Zheng、Ji-Chang Xiao

  DOI：10.1016/j.jfluchem.2020.109649

  日期：2020.12

  The development of efficient protocols for the synthesis of gem-difluoroolefins has received increasing attention. Given the ubiquity of hydroxyl group in biologically active molecules and synthetic intermediates, we developed a one-step protocol for the conversions of alcohols into gem-difluoroolefins. The reactions of alcohols with Ph3P+CF2CO2−/Burgess reagent in DMSO occurred smoothly to afford

  合成宝石-二氟烯烃的有效方案的开发受到越来越多的关注。考虑到生物活性分子和合成中间体中普遍存在羟基，我们开发了一种将醇类转化为宝石-二氟烯烃的一步方法。的Ph醇的反应3 P + CF 2 CO 2 - / Burgess试剂在DMSO发生顺利，得到最终的产品在较高产率。DMSO不仅是氧化过程所必需的，而且对于通过捕集二氟卡宾来稳定叶立德也很重要。
• [3 + 2]-Annulation of <i>gem</i>-Difluoroalkenes and Pyridinium Ylides: Access to Functionalized 2-Fluoroindolizines
  作者：Jun-Qi Zhang、Dandan Hu、Jinyu Song、Hongjun Ren

  DOI：10.1021/acs.joc.0c03041

  日期：2021.3.19

  A [3 + 2]-annulation of gem-difluoroalkenes and pyridinium ylides was developed employing ambient air as the sole oxidant in an open-vessel manner, affording a series of multifunctionalized 2-fluoroindolizines in moderate to good yields. In this reaction, gem-difluoroalkene acts as a C2 synthon and entirely avoids the competitive addition–elimination process, which provides facile access to 2-fluoroindolizines

  开发了宝石-二氟烯烃和吡啶鎓吡啶鎓的[3 + 2]环空反应，以开敞的方式使用环境空气作为唯一的氧化剂，以中等至良好的收率提供了一系列多官能化的2-氟吲哚并嗪。在该反应中，宝石-二氟烯烃充当C2合成子，完全避免了竞争性加成-消除过程，该过程提供了轻松获得2-氟吲哚嗪的途径。
• Deoxygenative <i>gem</i>-difluoroolefination of carbonyl compounds with (chlorodifluoromethyl)trimethylsilane and triphenylphosphine
  作者：Fei Wang、Lingchun Li、Chuanfa Ni、Jinbo Hu

  DOI：10.3762/bjoc.10.32

  日期：——

  phosphonium ylide represents one of the most straightforward methods. RESULTS: The combination of (chlorodifluoromethyl)trimethylsilane (TMSCF2Cl) and triphenylphosphine (PPh3) can be used for the synthesis of gem-difluoroolefins from carbonyl compounds. Comparative experiments demonstrate that TMSCF2Cl is superior to (bromodifluoromethyl)trimethylsilane (TMSCF2Br) and (trifluoromethyl)trimethylsilane

  背景：1,1-二氟烯烃不仅可以作为有机合成的有价值的前体，还可以作为酶抑制剂的生物电子等排体。在其制备的各种方法中，用二氟亚甲基鏻叶立德进行羰基烯化是最直接的方法之一。结果：（氯二氟甲基）三甲基硅烷（TMSCF2Cl）和三苯基膦（PPh3）的组合可用于由羰基化合物合成钆二氟烯烃。对比实验表明，在该反应中，TMSCF2Cl 优于（溴二氟甲基）三甲基硅烷（TMSCF2Br）和（三氟甲基）三甲基硅烷（TMSCF3）。结论：与许多其他在 PPh3 存在下的 Wittig 型 gem-二氟烯烃化反应类似，TMSCF2Cl 与醛和活化酮的反应是有效的。
• Manganese-catalyzed synthesis of monofluoroalkenes via C–H activation and C–F cleavage
  作者：Sai-Hu Cai、Lu Ye、Ding-Xing Wang、Yi-Qiu Wang、Lin-Jie Lai、Chuan Zhu、Chao Feng、Teck-Peng Loh

  DOI：10.1039/c7cc04131d

  日期：——

  The manganese-catalyzed α-fluoroalkenylation of arenes via C–H activation and C–F cleavage has been described. This protocol provides a very useful method for the synthesis of monofluoroalkenes with predominant unconventional E-isomer selectivity which complements the existing strategies for the access to these molecular architectures. In addition, the selectivity of β-defluorination in the catalytic

  已经描述了通过C–H活化和C–F裂解的锰催化的芳烃α-氟代烯基化反应。该协议为合成具有主要非常规E-异构体选择性的单氟烯烃提供了一种非常有用的方法，该方法对现有的访问这些分子结构的策略进行了补充。此外，β-脱氟在催化循环中的选择性不仅决定了产物的构型，而且避免了使用外部氧化剂，这为开发锰催化的氧化还原-中性CH转化提供了一个很好的例子。