2-溴-1-乙烯基-4-氟苯 | 1221684-51-0

• 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: 2-溴-1-乙烯基-4-氟苯
• 英文名称: 2-bromo-4-fluoro-1-vinylbenzene
• 英文别名: 2-bromo-4-fluorostyrene；2-Bromo-1-ethenyl-4-fluorobenzene
• CAS: 1221684-51-0
• 化学式: C₈H₆BrF
• 分子量: 201.038
• InChiKey: MNKVLFONYODHBB-UHFFFAOYSA-N

物化性质

• 沸点：
  204.6±20.0℃ (760 Torr)
• 密度：
  1.480±0.06 g/cm3 (20 ºC 760 Torr)
• 闪点：
  80.2±16.6℃

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  10
• 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：
  1

安全信息

• 海关编码：
  2903999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Bromo-1-ethenyl-4-fluorobenzene
Synonyms:

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

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Bromo-1-ethenyl-4-fluorobenzene
CAS number: 1221684-51-0

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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.

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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.

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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.

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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, refrigerated.
Storage:

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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.

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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: C8H6BrF
Molecular weight: 201.0

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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, hydrogen bromide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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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.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-溴-1-乙烯基-4-氟苯 在 9-硼双环[3.3.1]壬烷 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 13.0h， 生成 2-(2-bromo-4-fluorophenyl)ethanol
  参考文献：
  名称：

  Enantioselective Construction of Spiro Quaternary Carbon Stereocenters via Pd-Catalyzed Intramolecular α-Arylation

  摘要：

  We herein report the development of a sterically hindered and electron-rich P-chiral monophosphorus biaryl ligand that has enabled a general and efficient enantioselective intramolecular alpha-arylation, providing access to a wide series of [4.4], [4.5], and [4.6]-spirocycles with chiral benzylic quaternary carbons in high yields with good to excellent enantioselectivities. A pronounced water effect on enantioselectivity is observed.

  DOI：

  10.1021/acs.orglett.0c01129
• 作为产物：
  描述：

  2-溴-4-氟苯甲腈 在 正丁基锂 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 14.5h， 生成 2-溴-1-乙烯基-4-氟苯
  参考文献：
  名称：

  分子内氨基钯催化引发的钯与烯烃催化的钯催化成环氨基烯化反应

  摘要：

  描述了钯催化的氨基钯反应，然后与醛类进行亲核加成反应并脱水。这种直接且操作简单的方法为广泛的官能化四氢异喹啉具有高选择性提供了一种快速可靠的方法。机理研究表明，通过高度有序的过渡态进行的亲核加成是营业额限制步骤，其中关键Csp 3 -Pd物种固有的β-氢化物消除是受约束构象和亲核性控制的。氮原子的强供电子作用增强了Csp 3 -Pd键。

  DOI：

  10.1002/anie.201611853

文献信息

• Direct synthesis of dialkylarylvinylsilane derivatives: metathesis of dialkylaryl-iso-propenylsilane and its application to tetracyclic silacycle dye synthesis
  作者：Shohei Yoshioka、Tsunayoshi Takehara、Tsuyoshi Matsuzaki、Takeyuki Suzuki、Hirofumi Tsujino、Tadayuki Uno、Yasuo Tsutsumi、Kenichi Murai、Hiromichi Fujioka、Mitsuhiro Arisawa

  DOI：10.1039/c9cc06777a

  日期：——

  The metathesis of dialkylarylvinylsilane, which has not been accomplished to date, is achieved using dialkylaryl-iso-propenylsilane as a substrate. In addition, we discovered that the reason why the metathesis of a ruthenium carbene complex and dialkylarylvinylsilane is difficult is the formation of a carbide complex.

  使用二烷基芳基-异丙烯基硅烷作为底物可以实现迄今为止尚未完成的二烷基芳基乙烯基硅烷的复分解反应。另外，我们发现钌卡宾配合物和二烷基芳基乙烯基硅烷难以复分解的原因是碳化物配合物的形成。
• Enantioselective Copper-Catalyzed Intermolecular Amino- and Azidocyanation of Alkenes in a Radical Process
  作者：Dinghai Wang、Fei Wang、Pinghong Chen、Zhenyang Lin、Guosheng Liu

  DOI：10.1002/anie.201611850

  日期：2017.2.13

  Asymmetric copper‐catalyzed intermolecular amino‐ and azidocyanation reactions of alkenes have been developed that proceed via a radical process in which a key benzylic radical intermediate is enantioselectively trapped by a chiral Box/CuII cyanide complex. A variety of enantiomerically enriched β‐amino/azido alkylnitriles were efficiently synthesized. The β‐azido alkylnitriles could be converted into

  已经开发出通过自由基过程进行的不对称铜催化的烯烃分子间的氨基和叠氮氰化反应，其中关键的苄基自由基中间体被手性的Box / Cu II氰化物络合物对映选择性地捕获。有效合成了多种对映体富集的β-氨基/叠氮基烷基腈。β-叠氮基烷基腈可以转化为一系列极有价值的基于光学活性胺的结构单元和生物活性化合物。
• Synthesis of bis-BN-Naphthalene-Fused Oxepins and Their Photoluminescence Including White-Light Emission
  作者：Dawei Tian、Qian Li、Yifan Zhao、Zijia Wang、Wenbin Li、Shuling Xia、Siyang Xing、Bolin Zhu、Jianying Zhang、Chunming Cui

  DOI：10.1021/acs.joc.9b02594

  日期：2020.1.17

  system. Interestingly, dual-fluorescent emissions were observed upon dissolving N-substituted derivatives 10-14 in dimethyl sulfoxide. Tunable emission colors especially for white-light emissions can be achieved by controlling the ratio of solvents, concentration, or temperature using only a single-molecule compound.

  通过溴化的2，1-硼硼烷萘和顺式双（硼基）烯烃的钯催化串联反应，合成了一系列新型的双-BN-萘稠合的环氧丙烷衍生物。X射线晶体学分析表明，双-BN-萘-融合的氧杂环丁烷具有平面框架。通过紫外可见光谱和荧光光谱以及密度泛函理论（DFT）计算研究了新型BN-萘基融合氧杂环丁烷的电子和光物理性质，该计算揭示了类似烃类系统的独特电子和光物理性质。有趣的是，将N-取代的衍生物10-14溶解在二甲基亚砜中观察到双荧光发射。通过控制溶剂的比例，浓度，
• Copper-Catalyzed Recycling of Halogen Activating Groups via 1,3-Halogen Migration
  作者：R. David Grigg、Ryan Van Hoveln、Jennifer M. Schomaker

  DOI：10.1021/ja306446m

  日期：2012.10.3

  A Cu(I)-catalyzed 1,3-halogen migration reaction effectively recycles an activating group by transferring bromine or iodine from a sp(2) to a benzylic carbon with concomitant borylation of the Ar-X bond. The resulting benzyl halide can be reacted in the same vessel under a variety of conditions to form an additional carbon-heteroatom bond. Cross-over experiments using an isotopically enriched bromide

  Cu(I) 催化的 1,3-卤素迁移反应通过将溴或碘从 sp(2) 转移到苄基碳并伴随 Ar-X 键的硼化，有效地回收了活化基团。所得苄基卤可以在同一容器中在各种条件下反应以形成额外的碳-杂原子键。使用同位素富集的溴化物源的交叉实验支持 Br 的分子内转移。假设该反应通过邻卤苯乙烯的马尔科夫尼科夫氢铜反应、所得 Cu(I) 络合物氧化加成到 Ar-X 键中、还原消除新的 sp(3) CX 键和最终硼化反应进行Ar-Cu(I) 物种翻转催化循环。
• Asymmetric Copper-Catalyzed Intermolecular Aminoarylation of Styrenes: Efficient Access to Optical 2,2-Diarylethylamines
  作者：Dinghai Wang、Lianqian Wu、Fei Wang、Xiaolong Wan、Pinhong Chen、Zhenyang Lin、Guosheng Liu

  DOI：10.1021/jacs.7b02455

  日期：2017.5.24

  After addition to styrene, the generated benzylic radical could couple with a chiral L*CuIIAr complex to achieve enantioselective arylation. Various optical 2,2-diarylethylamines were efficiently synthesized from simple styrenes with high enantioselectivity, and these products can serve as valuable synthons toward bioactive molecules' synthesis.

  我们使用新型 N-氟-N-烷基磺酰胺作为胺试剂，开发了一种铜催化的烯烃对映选择性分子间氨基芳基化，它可以与 Cu(I) 催化剂反应以释放相关的氨基自由基。添加到苯乙烯后，生成的苄基自由基可以与手性 L*CuIIAr 络合物偶联以实现对映选择性芳基化。各种光学 2,2-二芳基乙胺以高对映选择性由简单的苯乙烯有效合成，这些产物可作为有价值的合成子用于生物活性分子的合成。