4-(苯基乙炔基)苯硼酸频哪醇酯 | 1190376-20-5

• 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-(苯基乙炔基)苯硼酸频哪醇酯
• 英文名称: 4,4,5,5-tetramethyl-2-[4-(2-phenylethynyl)phenyl]-1,3,2-dioxaborolane
• 英文别名: 4-(phenylethynyl)phenylboronic acid pinacol ester；4,4,5,5-tetramethyl-2-(4-(phenylethynyl)phenyl)-1,3,2-dioxaborolane；4,4,5,5-Tetramethyl-2-(4-phenylethynyl-phenyl)-[1,3,2]dioxaborolane
• CAS: 1190376-20-5
• 化学式: C₂₀H₂₁BO₂
• 分子量: 304.197
• InChiKey: AAIDERXZGJSORP-UHFFFAOYSA-N

物化性质

• 熔点：
  96-100°C
• 沸点：
  428.7±28.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温、干燥且密封保存。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 4-(Phenylethynyl)phenylboronic acid pinacol ester
CAS-No. : 1190376-20-5
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
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C20H21BO2
Molecular Weight : 304,19 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
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
no data available
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
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
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
Provide appropriate exhaust ventilation at places where dust is formed.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
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
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
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
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. 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: 96 - 100 °C
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 10,5 - (Air = 1.0)
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 5,932
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
no data available
Incompatible materials
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
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause 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.
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：

  4-(苯基乙炔基)苯硼酸频哪醇酯 在 5,5-dioxido-2,8-bis(trifluoromethyl)-10H-dibenzo[b,e][1,4]thiabismin-10-yl 2,2,2-trifluoroacetate 、 2,6-dichloro-1-fluoropyridin-1-ium tetrafluoroborate 作用下， 以 氯仿 为溶剂， 以49%的产率得到1-氟-4-苯基乙炔-苯
  参考文献：
  名称：

  Bi(V)氟化物形成芳基-F键的机理

  摘要：

  在本文中，我们描述了中性和阳离子高价有机铋(V)氟化物形成C(sp 2 )–F键的联合实验和理论机理研究，其特征是双阴离子双芳基亚磺酰亚胺配体。对配体、亚磺酰亚胺和中性二氟化三芳基铋(V)上的反应性芳基的取代模式的详尽评估表明，溶液中二聚结构的形成促进了Ar-F键的容易形成。值得注意的是，中性二氟化铋（V）还原消除的理论模型与实验确定的动力学和热力学参数一致。此外，添加外部氟化物源会产生无活性的八面体阴离子三氟化铋盐，从而减缓还原消除。另一方面，对阳离子氟化铋的平行分析揭示了四氟硼酸根阴离子作为氟化物源的关键作用。实验和理论分析都得出结论，C-F 键的形成是通过低能五元过渡态途径发生的，其中 F 阴离子从 BF 4阴离子传递到 C(sp 2 ) 中心，让人想起巴尔兹-希曼反应。在整个研究过程中收集的知识可以对几种配体的关键参数进行合理评估，确定简单的基于砜的配体家族作为芳基硼酸衍生物化学计量和催化氟化的改进系统。

  DOI：

  10.1021/jacs.2c01072
• 作为产物：
  描述：

  lithium phenylacetylide 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 4-(苯基乙炔基)苯硼酸频哪醇酯
  参考文献：
  名称：

  使用三有机铟试剂将铱催化的 C-H 硼化与钯催化的交叉偶联合并

  摘要：

  通过将 Ir 催化的 C-H 硼化 (CHB) 与化学选择性钯催化的三有机铟试剂的交叉偶联相结合，开发了一种制备具有烷基、烯基、炔基、芳基和杂芳基官能团的硼化芳烃的通用且有效的方法。 Sarandeses-Sestelo 偶联）与带有硼酸酯取代基的芳基卤化物。使用三有机铟交叉偶联反应引入不饱和部分可以合成通过直接应用 CHB 方法难以获得的硼化芳烃。顺序双催化程序也可以在一个容器中进行。

  DOI：

  10.1021/acs.joc.1c01978

文献信息

• Facile Regio- and Stereoselective Hydrometalation of Alkynes with a Combination of Carboxylic Acids and Group 10 Transition Metal Complexes: Selective Hydrogenation of Alkynes with Formic Acid
  作者：Ruwei Shen、Tieqiao Chen、Yalei Zhao、Renhua Qiu、Yongbo Zhou、Shuangfeng Yin、Xiangbo Wang、Midori Goto、Li-Biao Han

  DOI：10.1021/ja2069246

  日期：2011.10.26

  highly stereo- and regioselective hydrometalation of alkynes generating alkenylmetal complex is disclosed for the first time from a reaction of alkyne, carboxylic acid, and a zerovalent group 10 transition metal complex M(PEt(3))(4) (M = Ni, Pd, Pt). A mechanistic study showed that the hydrometalation does not proceed via the reaction of alkyne with a hydridometal generated by the protonation of a

  通过炔烃、羧酸和零价族 10 过渡金属络合物 M(PEt(3))(4) (M =镍、钯、铂）。一项机理研究表明，氢金属化不是通过炔烃与由羧酸与 Pt(PEt(3))(4) 质子化产生的氢化金属反应进行的，而是通过炔烃配位金属络合物与酸。这一发现阐明了长期以来提出的反应机制，该机制通过生成烯基钯中间体和随后在由 Brφnsted 酸和 Pd(0) 配合物的组合催化的各种反应中转化该配合物来进行。
• Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover
  作者：James P. Phelan、Simon B. Lang、Jordan S. Compton、Christopher B. Kelly、Ryan Dykstra、Osvaldo Gutierrez、Gary A. Molander

  DOI：10.1021/jacs.8b05243

  日期：2018.6.27

  A benchtop stable, bifunctional reagent for the redox-neutral cyclopropanation of olefins has been developed. Triethylammonium bis(catecholato)iodomethylsilicate can be readily prepared on multigram scale. Using this reagent in combination with an organic photocatalyst and visible light, cyclopropanation of an array of olefins, including trifluoromethyl- and pinacolatoboryl-substituted alkenes, can

  已开发出一种用于烯烃氧化还原中性环丙烷化的台式稳定双功能试剂。三乙基铵双（儿茶酚）碘甲基硅酸盐可以很容易地以多克规模制备。将该试剂与有机光催化剂和可见光结合使用，可以在数小时内完成一系列烯烃（包括三氟甲基和频哪醇硼基取代的烯烃）的环丙烷化反应。该反应对传统的反应性官能团（羧酸、碱性杂环、卤代烷等）具有高度耐受性，并允许聚烯烃化合物的化学选择性环丙烷化。机理研究表明，反应通过快速阴离子 3-exotet 环闭合进行，该途径与实验和计算数据一致。
• Cross‐Coupling through Ag(I)/Ag(III) Redox Manifold
  作者：Luca Demonti、Nathalie Saffon‐Merceron、Nicolas Mézailles、Noel Nebra

  DOI：10.1002/chem.202102836

  日期：2021.11.5

  trifluoromethylation via AgI/AgIII redox shuttles are herein deciphered. This innovative cross-coupling, analogous to the CEL coupling popularized by copper, involves: i) easy AgI/AgIII 2e− oxidation; ii) phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) benzotrifluoride production from aryl-AgIII intermediates. Now, AgIIICF3 chemistry is safe and reachable from AgF, KF, CF3TMS and air.

  教银做伎俩。通过Ag I / Ag III氧化还原穿梭进行氧化三氟甲基化的最关键步骤在本文中被破译。这种创新的交叉耦合类似于铜普及的 CEL 耦合，包括：i)容易的 Ag I /Ag III 2 e -氧化；ii)苯连接到 Ag III 上；iii)硼到 Ag III芳基转移；和ⅳ）三氟甲苯产量从芳基的Ag III中间体。现在，Ag III CF 3化学是安全的，可以从 AgF、KF、CF 3 TMS 和空气中获得。
• An Amine-Assisted Ionic Monohydride Mechanism Enables Selective Alkyne <i>cis</i>-Semihydrogenation with Ethanol: From Elementary Steps to Catalysis
  作者：Zhidao Huang、Yulei Wang、Xuebing Leng、Zheng Huang

  DOI：10.1021/jacs.1c01472

  日期：2021.3.31

  protonolysis of the Ir–C(vinyl) bond. Instead, mechanistic data are consistent with an anion-involved alcoholysis pathway involving ionization of (NCP)IrCl(vinyl) via EtOH-for-Cl substitution and reversible protonation of Cl– ion with an Ir(III)-bound EtOH, followed by β-H elimination of the ethoxy ligand and C(vinyl)–H reductive elimination. The use of an amine is key to the monohydride mechanism by promoting

  Z-烯烃在炔烃半加氢反应中的选择性合成取决于催化剂对起始原料和产物的反应性差异。在这里，我们报告了通过配位诱导的离子一氢化物机制用乙醇对炔烃进行Z选择性半氢化。EtOH 配位驱动的 Cl –在钳形 Ir(III) 氢氯化物络合物 (NCP)IrHCl ( 1 ) 中解离形成阳离子一氢化物，[(NCP)IrH(EtOH)] + Cl –，它选择性地与炔烃反应相应的Z-烯烃，从而克服竞争性热力学主导烯烃Z - E异构化和过度还原。然而，建立催化循环的挑战在于醇解步骤；炔烃插入产物 (NCP)IrCl(乙烯基) 与 EtOH 的反应确实发生，但非常缓慢。令人惊讶的是，醇解不是通过 Ir-C（乙烯基）键的直接质子分解进行的。相反，机理数据与涉及阴离子的醇解途径一致，包括 (NCP)IrCl(vinyl) 通过 EtOH-for-Cl 取代电离和 Cl -离子与 Ir(III) 结合的 EtOH 的可逆质子化，然后是
• Mild, Selective Ru‐Catalyzed Deuteration Using D ₂ O as a Deuterium Source
  作者：Pascal Eisele、Franziska Ullwer、Sven Scholz、Bernd Plietker

  DOI：10.1002/chem.201904927

  日期：2019.12.20

  A method for the selective deuteration of polyfunctional organic molecules using catalytic amounts of [RuCl2 (PPh3 )3 ] and D2 O as a deuterium source is presented. Through variation of additives like CuI, KOH, and various amounts of zinc powder, orthogonal chemoselectivities in the deuteration process are observed. Mechanistic investigation indicates the presence of different, defined Ru-complexes

  提出了一种使用催化量的 [RuCl2 (PPh3 )3 ] 和 D2 O 作为氘源选择性氘化多官能有机分子的方法。通过改变 CuI、KOH 和不同量的锌粉等添加剂，可以观察到氘化过程中的正交化学选择性。机理研究表明在给定的特定条件下存在不同的、确定的 Ru 配合物。