CAS: 83947-56-2; E-Phenylethenylboronic Acid, Pinacol Ester

• 英文名称E-Phenylethenylboronic Acid, Pinacol Ester
• 中文名称(E)-4,4,5,5-四甲基-2-苯乙烯基-1,3,2-二氧杂硼烷
• IUPAC名称(E)-4,4,5,5-tetramethyl-2-styryl-1,3,2-dioxaborolane
• 其它别名~-苯乙烯硼酸频哪酸酯; Trans-2-Styreneboronic Acid Pinacol Ester, Trans-2-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-yl)Styrene
• CAS编号83947-56-2
• MFCD编号:MFCD03453666
• EINECS号:641-148-1
• 分子式:C14H19BO2分子量:230.12
• 产品CID: 1827798
• 产品分类有机原料→分子砌块→芳环类化合物→苯类化合物

• 相似结构搜索
• InChIKey: ARAINKADEARZLZ-ZHACJKMWSA-N
• InChI=1S/C14H19BO2/c1-13(2)14(3,4)17-15(16-13)11-10-12-8-6-5-7-9-12/h5-11H,1-4H3/b11-10+
• 计算化学: 氢键受体数2.0氢键供体数*可旋转键数2.0

物理性质

• 熔点27-33°C
• 沸点271.9°C at 760 mmHg
• 闪点118.2°C
• 密度1.0±0.1 g/cm3
• PSA:18.46
• LogP:3.3312
• 折射率1.505
• 蒸汽压0.0±0.5 mmHg at 25°C
• 敏感性按规定使用和贮存的不会分解，避氧化物
• 外观形态透明无色至淡黄色液体
• 储存条件惰性气氛,存放于冰箱中, -20°C
• 产品应用该化合物用于PKC-抑制剂 PKCQ抑制剂

MSDS等安全信息

• GHS象形图
• GHS符号GHS07;
  注释: Exclamation mark
• 危险类别特定目标器官毒性 - 单次接触 类别3
  皮肤腐蚀/刺激 类别2
  严重眼刺激 类别2
  严重眼刺激 类别2A
  急性毒性 类别4(吸入)
  急性毒性 类别4(经皮)
  急性毒性 类别4(经口)
• 警示词Warning(警告)
• 危险描述H335 |可能引起呼吸道刺激.
  H315 |造成皮肤刺激.
  H319 |造成严重眼刺激.
  H332 |吸入有害.
  H312 |皮肤接触有害.
  H302 |吞咽有害.
• 防范说明P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
• 安全声明H302 (33.33%)H312 (33.33%)H315 (100%)
• WGK Germany3

欧盟法规

上下游产品

合成工艺路线路线简述

• 76-09-5 + 588-72-7 = 83947-56-2
  反应条件:1.1 Solvents: Tetrahydrofuran; 3 H,Rt
  标题:Oxygen-Promoted Palladium(Ii) Catalysis: Facile C(Sp2)-C(Sp2) Bond Formation Via Cross-Coupling Of Alkenylboronic Compounds And Olefins
  作者:Yoon,Cheol Hwan; Et Al
  参考文献:Organic Letters 日期:2004 卷标:6(22) 页码:4037-4039]
  
  591-50-4 + 75927-49-0 = 83947-56-2
  反应条件:1.1 Reagents: Tributylamine Catalysts: Tetrakis(Triphenylphosphine)Palladium Solvents: Acetonitrile
  标题:Synthesis Of Trans-Arylvinylboronates Via A Palladium Catalyzed Cross-Coupling Of A Vinylboronate Ester With Aryl Halides
  作者:Stewart,Sarah K.; Et Al
  参考文献:Journal Of Organometallic Chemistry 日期:1994 卷标:482(1-2) 页码:293-300]
  
  76-09-5 + 6783-05-7 = 83947-56-2
  反应条件:1.1 Solvents: Tetrahydrofuran; 3 H,Rt
  标题:Oxidative Palladium(Ii) Catalysis: A Highly Efficient And Chemoselective Cross-Coupling Method For Carbon-Carbon Bond Formation Under Base-Free And Nitrogenous-Ligand Conditions
  作者:Yoo,Kyung Soo; Et Al
  参考文献:Journal Of The American Chemical Society 日期:2006 卷标:128(50) 页码:16384-16393]
  
  76-09-5 + 6783-05-7 = 83947-56-2
  反应条件:1.1 Solvents: Diethyl Ether
  标题:Pinacolyl Boronic Esters As Components In The Petasis Reaction
  作者:Koolmeister,Tobias; Et Al
  参考文献:Tetrahedron Letters 日期:2002 卷标:43(34) 页码:5965-5968]
  
  69190-62-1 = 83947-56-2
  反应条件:1.1 Reagents: Magnesium,Butylhydro- Solvents: Toluene-D8; 16 H,80 °C
  标题:Magnesium-Catalyzed Hydroboration Of Terminal And Internal Alkynes
  作者:Magre,Marc; Et Al
  参考文献:Angewandte Chemie 日期:2019 卷标:58(21) 页码:7025-7029]
  
  73183-34-3 = 83947-56-2
  反应条件:1.1 Catalysts: Copper Nitride (Cu3N) Solvents: Ethanol; 1 H,30 °C
  标题:A Copper Nitride Nanocube Catalyst For Highly Efficient Hydroboration Of Alkynes
  作者:Xu,Hang; Et Al
  参考文献:Organic & Biomolecular Chemistry 日期:2023 卷标:21(7) 页码:1404-1410]
  
  75927-49-0 = 83947-56-2
  反应条件:1.1 Catalysts: Polyethylene Glycol Dimethyl Ether,Carbonylchlorohydrobis(Tricyclohexylphosphine)Ruthenium; 18 H,110 °C
  标题:Peg-Mediated Recyclable Borylative Coupling Of Vinyl Boronates With Olefins
  作者:Szyling,Jakub; Et Al
  参考文献:Journal Of Catalysis 日期:2019 卷标:376 页码:219-227]
  
  76-09-5 = 83947-56-2
  反应条件:1.1 Reagents: Catechol,(T-4)-Trihydro(Tetrahydrofuran)Boron Solvents: Tetrahydrofuran; 0 °C; 0.5 H,0 °C; 1 H,Rt1.2 Catalysts: Dicyclohexylborane Solvents: Tetrahydrofuran; 0 °C; 2 H,Rt1.3 0 °C; 18 H,Rt1.4 Reagents: Oxygen; 2 H,Rt
  标题:Preparation Of (E)-1-Alkenylboronic Acid Pinacol Esters Via Transfer Of Alkenyl Group From Boron To Boron
  作者:Shirakawa,Kazuya; Et Al
  参考文献:Synthesis 日期:2004 卷标:(11) 页码:1814-1820]
  
  25015-63-8 = 83947-56-2
  反应条件:1.1 Reagents: Norbornene Catalysts: Tetrakis(Trimethylphosphine)Iron Solvents: Hexane; 18 H,50 °C
  标题:Iron-Catalyzed E-Selective Dehydrogenative Borylation Of Vinylarenes With Pinacolborane
  作者:Wang,Chao; Et Al
  参考文献:Acs Catalysis 日期:2016 卷标:6(11) 页码:7585-7589]
  
  76-09-5 + 201852-49-5 = 83947-56-2
  反应条件:1.1 Reagents: Chlorotrimethylsilane,Potassium Carbonate Solvents: Acetonitrile
  标题:Pd-Catalyzed Coupling Of Benzyl Bromides With Bmida-Substituted N-Tosylhydrazones: Synthesis Of Trans-Alkenyl Mida Boronates
  作者:Li,Shichao; Et Al
  参考文献:Chemical Communications (Cambridge 日期:2022 卷标:58(3) 页码:399-402]
  
  74213-48-2 = 83947-56-2
  反应条件:1.1 Reagents: Tripotassium Phosphate Catalysts: Bis(Acetylacetonato)Nickel,Zinc,1,1′-(9,9-Dimethyl-9H-Xanthene-4,5-Diyl)Bis[1,1-Diphenylphosphine] Solvents: Toluene,Cyclohexane; 24 H,120 °C
  标题:Nickel(Ii)-Catalyzed Borylation Of Alkenyl Methyl Ethers Via C-O Bond Cleavage
  作者:Qiu,Xiaodong; Et Al
  参考文献:Organic Letters 日期:2020 卷标:22(16) 页码:6424-6428]
  
  74213-48-2 = 83947-56-2
  反应条件:1.1 Catalysts: Di-μ-Chlorobis[(1,2,5,6-η)-1,5-Cyclooctadiene]Dirhodium,1,1′-(9,9-Dimethyl-9H-Xanthene-4,5-Diyl)Bis[1,1-Diphenylphosphine] Solvents: Diisopropyl Ether; 10 Min,Rt1.2 Reagents: Potassium Carbonate,Bis(Pinacolato)Diborane; 10 Min,Rt1.3 Solvents: Diisopropyl Ether; 12 H,70 °C
  标题:Stereoselective Synthesis Of Vinylboronates By Rh-Catalyzed Borylation Of Stereoisomeric Mixtures
  作者:Li,Shenhuan; Et Al
  参考文献:Chinese Journal Of Chemistry 日期:2019 卷标:37(5) 页码:462-468]
  
  83622-41-7 + 100-52-7 = 83947-56-2
  反应条件:1.1 Reagents: Chlorotrimethylsilane,Manganese,Lithium Iodide Catalysts: Trichlorotris(Tetrahydrofuran)Chromium Solvents: Tetrahydrofuran; 30 Min,25 °C1.2 Solvents: Tetrahydrofuran; 4 H,25 °C; 2 H,25 °C
  标题:Transformation Of Aldehydes Into (E)-1-Alkenylsilanes And (E)-1-Alkenylboronic Esters With A Catalytic Amount Of A Chromium Salt
  作者:Takai,Kazuhiko; Et Al
  参考文献:Bulletin Of The Chemical Society Of Japan 日期:2004 卷标:77(8) 页码:1581-1586]
  
  108387-99-1 + 73183-34-3 = 83947-56-2
  反应条件:1.1 Catalysts: Triethylphosphine,Bis[(1,2,5,6-η)-1,5-Cyclooctadiene]Di-μ-Hydroxydirhodium Solvents: Diethyl Ether,Tetrahydrofuran; 6 H,50 °C; 50 °C -> Rt1.2 Reagents: Ammonium Chloride Solvents: Water; Rt
  标题:Facile Transformation Of αβ-Unsaturated Carboxylic Acids To Alkenylboronic Esters Via Rhodium-Catalyzed Decarbonylative Borylation Of α,β-Unsaturated Thioesters
  作者:Niwa,Takashi; Et Al
  参考文献:Chemistry Letters 日期:2017 卷标:46(9) 页码:1315-1318]
  
  73183-34-3 = 83947-56-2
  反应条件:1.1 Reagents: Triethylaluminum Catalysts: (Sp-4-1)-[bis[2-[bis[4-(Trifluoromethyl)Phenyl]Phosphino-Kp]Phenyl]Methylsilyl-K... Solvents: Toluene; 6 H,60 °C
  标题:Psip-Pincer Type Palladium-Catalyzed Dehydrogenative Borylation Of Alkenes And 1,3-Dienes
  作者:Kirai,Naohiro; Et Al
  参考文献:Bulletin Of The Chemical Society Of Japan 日期:2013 卷标:86(7) 页码:784-799]
  
  25015-63-8 = 83947-56-2
  反应条件:1.1 Solvents: Tetrahydrofuran; 24 H,70 °C; 70 °C -> Rt1.2 Reagents: Oxygen; Rt
  标题:Hydroboration Of Terminal Alkenes And Trans-1,2-Diboration Of Terminal Alkynes Catalyzed By A Manganese(I) Alkyl Complex
  作者:Weber,Stefan; Et Al
  参考文献:Angewandte Chemie 日期:2021 卷标:60(46) 页码:24488-24492]
  
  25015-63-8 = 83947-56-2
  反应条件:1.1 Catalysts: 2360835-90-9; 8 H,30 °C
  标题:Aluminium Complex-Catalyzed Hydroboration Of Alkenes And Alkynes
  作者:Harinath,Adimulam; Et Al
  参考文献:New Journal Of Chemistry 日期:2019 卷标:43(26) 页码:10531-10536]
  
  25015-63-8 = 83947-56-2
  反应条件:1.1 Catalysts: 1-Ethyl-3-Methylimidazolium Trifluoromethanesulfonate,Carbonylchlorohydrobis(Triphenylphosphine)Ruthenium Solvents: Carbon Dioxide,Carbon Dioxide; 3 H,50 - 55 Bar,40 °C
  标题:Recyclable Hydroboration Of Alkynes Using Ruh@il And Ruh@il/scco2 Catalytic Systems
  作者:Szyling,Jakub; Et Al
  参考文献:Acs Sustainable Chemistry & Engineering 日期:2018 卷标:6(8) 页码:10980-10988]
  
  591-50-4 + 75927-49-0 = 83947-56-2
  反应条件:1.1 Reagents: Bis(Trifluoroacetoxy)Iodobenzene,Bis(Pinacolato)Diborane Catalysts: (Sp-4-3)-[2,6-Bis[(Dimethylamino-Kn)Methyl]Phenyl-Kc]Bromopalladium Solvents: Dichloromethane; 16 H,20 °C1.2 Reagents: Cesium Carbonate Solvents: Tetrahydrofuran,Water; 20 H,60 °C
  标题:Selective C-H Borylation Of Alkenes By Palladium Pincer Complex Catalyzed Oxidative Functionalization
  作者:Selander,Nicklas; Et Al
  参考文献:Angewandte Chemie 日期:2010 卷标:49(24) 页码:4051-4053]
  
  76-09-5 + 6783-05-7 = 83947-56-2
  反应条件:1.1 Solvents: Tetrahydrofuran; 3 H,Rt
  标题:Boron Trichloride-Mediated Synthesis Of Indoles Via The Aminoboration Of Alkynes
  作者:Lv,Jiahang; Et Al
  参考文献:Advanced Synthesis & Catalysis 日期:2018 卷标:360(21) 页码:4054-4059]
  
  73183-34-3 = 83947-56-2
  反应条件:1.1 Reagents: Triphenylphosphine Catalysts: Copper Oxide (Cu2O) Solvents: 1,4-Dioxane; 5 H,60 °C
  标题:Polyhedral Cu2O Crystals For Diverse Aryl Alkyne Hydroboration Reactions
  作者:Tsai,Hsin-Yi; Et Al
  参考文献:Chemistry - A European Journal 日期:2019 卷标:25(5) 页码:1300-1303]
  
  73183-34-3 = 83947-56-2
  反应条件:1.1 Catalysts: Sodium Tert-Butoxide,Cuprous Chloride,Bis[2-(Diphenylphosphino)Phenyl] Ether Solvents: Tetrahydrofuran; 30 Min,Rt1.2 Solvents: Tetrahydrofuran; 10 Min,Rt1.3 Reagents: Methanol; 24 H,Rt
  标题:Copper-Catalyzed Boration Of Activated Alkynes. Chiral Boranes Via A One-Pot Copper-Catalyzed Boration And Reduction Protocol
  作者:Jung,Ho-Young; Et Al
  参考文献:Tetrahedron 日期:2012 卷标:68(17) 页码:3444-3449]
  
  75927-49-0 = 83947-56-2
  反应条件:1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-Cyclooctadiene]Di-μ-Methoxydirhodium,1,1′-(9,9-Dimethyl-9H-Xanthene-4,5-Diyl)Bis[1,1-Diphenylphosphine] Solvents: 1,4-Dioxane; 16 H,90 °C
  标题:Transfer C-H Borylation Of Alkenes Under Rh(I)-Catalysis: Insight Into The Mechanism,Selectivity-Control & Synthetic Capacity
  作者:Veth,Lukas; Et Al
  参考文献:Chemrxiv 日期:2021 卷标:1 页码:1-12]
  
  73183-34-3 + 637-44-5 = 83947-56-2
  反应条件:1.1 Catalysts: Copper Oxide (Cu2O) Solvents: 1,4-Dioxane; 18 H,100 °C
  标题:Copper-Catalyzed Decarboxylative Hydroboration Of Phenylpropiolic Acids Under Ligand-Free Or Both Ligand- And Base-Free Conditions
  作者:Zhao,Ying-Wei; Et Al
  参考文献:Chinese Chemical Letters 日期:2016 卷标:27(4) 页码:571-574]
  
  25015-63-8 = 83947-56-2
  反应条件:1.1 Catalysts: Di-μ-Chlorobis[(1,2,5,6-η)-1,5-Cyclooctadiene]Dirhodium Solvents: Toluene
  标题:Rhodium- And Ruthenium-Catalyzed Dehydrogenative Borylation Of Vinylarenes With Pinacolborane: Stereoselective Synthesis Of Vinylboronates
  作者:Murata,Miki; Et Al
  参考文献:Bulletin Of The Chemical Society Of Japan 日期:2002 卷标:75(4) 页码:825-829]
  
  25015-63-8 = 83947-56-2
  反应条件:1.1 Catalysts: 2781183-95-5 Solvents: Toluene; 12 H,100 °C
  标题:Group 4 Metallocene Complexes Supported By A Redox-Active O,C-Chelating Ligand
  作者:Zhao,Qiuting; Et Al
  参考文献:Organometallics 日期:2022 卷标:41(12) 页码:1488-1500]
  
  73183-34-3 + 6783-05-7 = 83947-56-2
  反应条件:1.1 Solvents: Diethyl Ether,Pentane
  标题:Enantioselective Conjunctive Cross-Coupling Of Bis(Alkenyl)Borates: A General Synthesis Of Chiral Allylboron Reagents
  作者:Edelstein,Emma K.; Et Al
  参考文献:Journal Of The American Chemical Society 日期:2017 卷标:139(14) 页码:5027-5030]
  
  72824-05-6 = 83947-56-2
  反应条件:1.1 Catalysts: Grubbs Second Generation Catalyst Solvents: Dichloromethane; 12 H,Reflux
  标题:Synthesis Of Functionalized Vinyl Boronates Via Ruthenium-Catalyzed Olefin Cross-Metathesis And Subsequent Conversion To Vinyl Halides
  作者:Morrill,Christie; Et Al
  参考文献:Journal Of Organic Chemistry 日期:2003 卷标:68(15) 页码:6031-6034]
  
  76-09-5 + 201852-49-5 = 83947-56-2
  反应条件:1.1 Reagents: Chlorotrimethylsilane,Potassium Carbonate Solvents: Acetonitrile; 2 H,Rt
  标题:A General Method For Interconversion Of Boronic Acid Protecting Groups: Trifluoroborates As Common Intermediates
  作者:Churches,Quentin I.; Et Al
  参考文献:Journal Of Organic Chemistry 日期:2015 卷标:80(11) 页码:5428-5435]
  
  1566-65-0 + 73183-34-3 = 83947-56-2
  反应条件:1.1 Catalysts: Di-μ-Chlorobis[(1,2,5,6-η)-1,5-Cyclooctadiene]Dirhodium,1,1′-(9,9-Dimethyl-9H-Xanthene-4,5-Diyl)Bis[1,1-Diphenylphosphine] Solvents: Diisopropyl Ether; 10 Min,Rt1.2 Reagents: Potassium Carbonate; 10 Min,Rt1.3 Solvents: Diisopropyl Ether; 12 H,70 °C
  标题:Stereoselective Synthesis Of Vinylboronates By Rh-Catalyzed Borylation Of Stereoisomeric Mixtures
  作者:Li,Shenhuan; Et Al
  参考文献:Chinese Journal Of Chemistry 日期:2019 卷标:37(5) 页码:462-468]
  
  25015-63-8 = 83947-56-2
  反应条件:1.1 Catalysts: Potassium Tert-Butoxide,Cobalt,Dichloro[4′-(4-Pyridinyl)-2,2′:6′,2′′-Terpyridine-Kn1,Kn1′,Kn1′′]-,(Sp-... Solvents: Tetrahydrofuran; 1 Min,Rt1.2 10 Min,Rt1.3 Reagents: Dichloromethane
  标题:Highly Efficient And Selective Hydroboration Of Terminal And Internal Alkynes Catalyzed By A Cobalt(Ii) Coordination Polymer
  作者:Zhang,Guoqi; Et Al
  参考文献:Organic Chemistry Frontiers 日期:2019 卷标:6(18) 页码:3228-3233]
  
  1195-66-0 = 83947-56-2
  反应条件:1.1 Reagents: Diisobutylaluminum Hydride Catalysts: Bis(Triphenylphosphine)Nickel Dichloride Solvents: Tetrahydrofuran; 22 °C -> 0 °C1.2 5 Min,0 °C; 0 °C -> 22 °C; 6 H,22 °C1.3 24 H,22 °C
  标题:α-Selective Ni-Catalyzed Hydroalumination Of Aryl- And Alkyl-Substituted Terminal Alkynes: Practical Syntheses Of Internal Vinyl Aluminums,Halides,Or Boronates
  作者:Gao,Fang; Et Al
  参考文献:Journal Of The American Chemical Society 日期:2010 卷标:132(32) 页码:10961-10963

海关参考信息

• 2901210000-乙烯
  2902300000-甲苯
  2902500000-苯乙烯
  2905122000-异丙醇
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• ➥ 象形图和危险代码
• ➥ 防范代码详解
• ➥ 危险代码说明
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