反式-苯乙烯三氟硼酸钾 | 201852-49-5

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟硼酸钾系列
• 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: 反式-苯乙烯三氟硼酸钾
• 中文别名: 反式苯乙烯基三氟硼酸钾；反-Β-苯乙烯三氟硼酸钾；~-苯乙烯三氟硼酸钾；反式-β-苯乙烯三氟硼酸钾；反式-苯乙烯基三氟硼酸钾
• 英文名称: potassium (E)-trifluoro(styryl)borate
• 英文别名: potassium trans-styryltrifluoroborate；potassium (E)-styryltrifluoroborate；potassium trans-2-phenylvinyltrifluoroborate；potassium trans-β-styryltrifluoroborate；potassium 2-(E)-phenylethenyltrifluoroborate；potassium (E)-2-phenylvinyltrifluoroborate；potassium β-styryltrifluoroborate；potassium styryltrifluoroborate；potassium;trifluoro-[(E)-2-phenylethenyl]boranuide
• CAS: 201852-49-5
• 化学式: C₈H₇BF₃*K
• 分子量: 210.048
• InChiKey: NONAUTDEFRJJII-UHDJGPCESA-N

物化性质

• 熔点：
  >300°C
• 稳定性/保质期：
  避氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  0.09
• 重原子数：
  13
• 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：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  保存方法：密封、存于阴凉、通风干燥处。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Potassium trans-styryltrifluoroborate
CAS-No. : 201852-49-5
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
Safety data sheet available on request.
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36 Wear suitable protective clothing.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C8H7BF3K
Molecular Weight : 210,05 g/mol
Component Concentration
Potassium trans-styryltrifluoroborate
CAS-No. 201852-49-5 -

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Hydrogen fluoride, Borane/boron oxides, Potassium oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Store under inert gas. Moisture sensitive. Metals
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: > 300 °C - lit.
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
Avoid moisture.
Incompatible materials
Metals, glass, Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  反式-苯乙烯三氟硼酸钾 在 三氯异氰尿酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 0.67h， 以85%的产率得到(E)-β-chlorostyrene
  参考文献：
  名称：

  Metal-Free Chlorodeboronation of Organotrifluoroborates

  摘要：

  A mild and metal-free method for the chlorodeboronation of organotrifluoroborates using trichloroisocyanuric acid (TCICA) was developed. Aryl-, heteroaryl-, alkenyl-, alkynyl-, and alkyltrifluoroborates were converted into the corresponding chlorinated products in good yields. This method proved to be tolerant of a broad range of functional groups.

  DOI：

  10.1021/jo201313a
• 作为产物：
  描述：

  反式-BETA-苯乙烯硼酸 在 二氟化氢钾 作用下， 以 乙醚 、 水 为溶剂， 生成 反式-苯乙烯三氟硼酸钾
  参考文献：
  名称：

  Lewis酸促进的Friedel-Crafts与α-酮磷酸亲电试剂的烷基化反应

  摘要：

  描述了BF 3 ·OEt 2促进的α-芳基-α-酮磷酸盐的亲核取代，以提供α，α-二芳基酮产物。富含电子的α-酮磷酸酯的性能最佳，同时还可以耐受电子中性和贫电子的底物。该反应可耐受多种芳族，杂芳族和非芳族亲核试剂，收率范围为44％至84％。富含对映体的原料产生外消旋产物，表明通过酰基carb离子的S N 1途径。

  DOI：

  10.1021/ol100410k
• 作为试剂：
  描述：

  2-phenyl-1-(1-(o-tolyl)-1H-imidazol-2-yl)ethanone 、 反式-苯乙烯三氟硼酸钾 在 二茂铁 、 Δ-Rh(acetonitrile)2(5-(tert-butyl)-2-phenylbenzo[d]thiazole)PF6 、 sodium methylate 、 tert-butylammonium hexafluorophosphate(V) 、 反式-苯乙烯三氟硼酸钾 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 (E)-2,4-diphenyl-1-(1-(o-tolyl)-1H-imidazol-2-yl)but-3-en-1-one
  参考文献：
  名称：

  2-酰基咪唑的电化学对映选择性亲核α-C(sp3)-H烯基化

  摘要：

  将电化学与不对称催化相结合，有望为构建非外消旋手性分子提供一种环境友好且有效的策略。然而，在实践中，手性催化剂在电极和溶液界面的电化学条件下的不稳定性或不相容性带来了重大挑战。在此，我们报道了一种催化不对称间接电解，采用氧化还原介体和手性铑路易斯酸的组合，实现了以前难以捉摸的对映选择性亲核α - C(sp 3 ) -酮的 H 烯基化。具体而言，2-酰基咪唑与链烯基三氟硼酸钾以高产率（高达 94%）和出色的对映选择性（27 个实例，≥99% ee）反应，无需任何额外的化学计量氧化剂（总共 40 个实例）。新的间接电合成可以缩放到克数量，并应用于天然产物隐藻素 A 和组织蛋白酶 K 抑制剂的中间体的直接合成。

  DOI：

  10.1021/jacs.2c01686

文献信息

• Concise Total Synthesis and Stereochemical Revision of (+)-Naseseazines A and B: Regioselective Arylative Dimerization of Diketopiperazine Alkaloids
  作者：Justin Kim、Mohammad Movassaghi

  DOI：10.1021/ja206743v

  日期：2011.9.28

  Concise and enantioselective total syntheses of (+)-naseseazines A and B are described. Our regioselective and directed dimerization of diketopiperazines provides their critical C3-C(sp(2)) linkages, an assembly with plausible biogenetic relevance. We revise the absolute stereochemistry of (+)-naseseazines A and B.

  描述了 (+)-naseseazines A 和 B 的简洁和对映选择性全合成。我们对二酮哌嗪的区域选择性和定向二聚化提供了其关键的 C3-C(sp(2)) 链接，这是一个具有合理生物遗传相关性的程序集。我们修改了 (+)-naseseazines A 和 B 的绝对立体化学。
• Silver‐Enabled General Radical Difluoromethylation Reaction with TMSCF ₂ H
  作者：Jun Yang、Shengqing Zhu、Fang Wang、Feng‐Ling Qing、Lingling Chu

  DOI：10.1002/anie.202014587

  日期：2021.2.19

  A silver‐mediated oxidative difluoromethylation of styrenes and vinyl trifluoroborates with TMSCF2H is reported for the first time. This method enables direct and facile access to CF2H‐alkenes from abundant alkenes with excellent functional‐group compatibility. Moreover, this Ag/TMSCF2H protocol could further enable a series of radical difluoromethylation reactions of a wide array of substrates, offering

  首次报道了用TMSCF 2 H对苯乙烯和三氟硼酸乙烯基酯进行银介导的氧化二氟甲基化。这种方法可以从丰富的烯烃中直接和轻松地获得CF 2 H-烯烃，并且具有出色的官能团相容性。此外，该Ag / TMSCF 2 H方案可以进一步实现一系列底物的一系列自由基二氟甲基化反应，从而为构建多样化的C-CF 2 H键提供通用和互补的平台。
• Rate Dependence on Inductive and Resonance Effects for the Organocatalyzed Enantioselective Conjugate Addition of Alkenyl and Alkynyl Boronic Acids to β-Indolyl Enones and β-Pyrrolyl Enones
  作者：Amy Boylan、Thien S. Nguyen、Brian J. Lundy、Jian-Yuan Li、Ravikrishna Vallakati、Sasha Sundstrom、Jeremy A. May

  DOI：10.3390/molecules26061615

  日期：——

  Two key factors bear on reaction rates for the conjugate addition of alkenyl boronic acids to heteroaryl-appended enones: the proximity of inductively electron-withdrawing heteroatoms to the site of bond formation and the resonance contribution of available heteroatom lone pairs to stabilize the developing positive charge at the enone β-position. For the former, the closer the heteroatom is to the

  影响烯基硼酸与杂芳基连接的烯酮共轭加成反应速率的两个关键因素：感应吸电子杂原子与成键位点的接近度以及可用杂原子孤对对稳定产生的正电荷的共振贡献在烯酮β-位。对于前者，杂原子距离烯酮β-碳越近，反应越快。对于后者，苄基阳离子电荷的共振稳定性更强，可加速反应。因此，反应速率通过感应吸电子元件的更接近而增加，但如果涉及共振效应，则观察到具有给电子能力的速率增加。提出了异构底物这些趋势的证据，并且这些见解的应用允许反应条件改善与以前有问题的底物的反应性。
• Microwave-enhanced cross-coupling of allyl chlorides with vinyltrifluoroborates
  作者：George W. Kabalka、Eric Dadush、Mohammad Al-Masum

  DOI：10.1016/j.tetlet.2006.08.043

  日期：2006.10

  The allylation of potassium alkenyltrifluoroborates with allyl chloride via a palladium catalyzed cross-coupling reaction occurs rapidly under microwave irradiation. The allylation reaction produces 1,4-pentadienes in high yields.

  链烯基三氟硼酸钾通过钯催化的交叉偶联反应与烯丙基氯的烯丙基化在微波辐射下迅速发生。烯丙基化反应以高产率产生1，4-戊二烯。
• Tertiary and Quaternary Carbon Formation via Gallium-Catalyzed Nucleophilic Addition of Organoboronates to Cyclopropanes
  作者：Truong N. Nguyen、Jeremy A. May

  DOI：10.1021/acs.orglett.7b03349

  日期：2018.1.5

  via homoconjugate addition of organoboron nucleophiles to diester- and ketone-functionalized cyclopropanes. Electron donor group cyclopropane substituents were not needed, allowing electron-deficient aryl, alkenyl, alkyl, and hydrogen-substituted cyclopropanes to be used. The catalytic conditions were compatible with alkenyl, alkynyl, and aryl nucleophiles, including ortho-substituted aromatics, to

  GaCl 3和（IPr）GaCl 3 / AgSbF 6通过将有机硼亲核试剂均相加成到二酯和酮官能化的环丙烷上而形成γ-叔碳和γ-季碳。不需要电子供体基团的环丙烷取代基，从而可以使用缺电子的芳基，烯基，烷基和氢取代的环丙烷。催化条件与烯基，炔基和芳基亲核试剂（包括邻位取代的芳族化合物）相容，以合成高度受阻的季碳。炔基亲核试剂形成取代的环戊烯。对照实验支持季碳中心形成中的中间碳正离子化。