CAS: 87100-28-5; 2-Benzyl-4,4,5,5-Tetramethyl-1,3,2-Dioxaborolane

• 英文名称2-Benzyl-4,4,5,5-Tetramethyl-1,3,2-Dioxaborolane
• 中文名称苄基硼酸频哪醇酯
• IUPAC名称2-benzyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 其它别名4,4,5,5-Tetramethyl-2-(Phenylmethyl)-1,3,2-Dioxaborolane; Benzylboronic Acid Pinacol Ester; Ycnqpavkqplzrs-Uhfffaoysa-N; Benzylboronic Pinacol Ester; 2-Benzyl-4,4,5,5-Tetramethyl-1,3,2-Dioxab
• CAS编号87100-28-5
• MFCD编号:MFCD05663841
• EINECS号:679-569-8
• 分子式:C13H19BO2
• 分子量:218.1
• 产品CID: 1875986
• 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: YCNQPAVKQPLZRS-UHFFFAOYSA-N
• InChI=1S/C13H19BO2/c1-12(2)13(3,4)16-14(15-12)10-11-8-6-5-7-9-11/h5-9H,10H2,1-4H3…
• 计算化学: 氢键受体数2.0氢键供体数0可旋转键数2

物理性质

• 沸点269.6°C at 760 mmHg
• 闪点116.9°C
• 密度0.98
• PSA:18.46
• LogP:2.8605
• 折射率1.490
• 蒸汽压0.0±0.5 mmHg at 25°C
• 溶解性Insoluble In Water.
• 敏感性按规定使用和贮存的不会分解，避氧化物、潮湿
• 外观形态无色至淡黄色至浅橙色透明液体
• 储存条件惰性气氛,存放于冰箱中, -20°C
• 产品应用该化合物是许多天然产品和制药分子的关键合成中间体, 也是铃木-宫村的混合反应中的基本试剂.

MSDS等安全信息

• GHS象形图
• GHS符号GHS07;
  注释: Exclamation mark
• 危险类别皮肤腐蚀/刺激 类别2
  严重眼刺激 类别2
  特定目标器官毒性 - 单次接触 类别3
  严重眼刺激 类别2A
• 警示词Warning(警告)
• 危险描述H315 |造成皮肤刺激.
  H319 |造成严重眼刺激.
  H335 |可能引起呼吸道刺激.
• 防范说明P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
• 危险品标志Xi
• 风险等级Irritant
• 安全声明23-24/25
• WGK Germany3

欧盟法规

上下游产品

合成工艺路线路线简述

• 合成目标产物 Benzylboronic Acid Pinacol Ester 主要起始原料 Benzyl Chloride And Bis(Pinacolato)Diboron
• 73183-34-3 = 87100-28-5
  反应条件:1.1 Reagents: Potassium Tert-Butoxide Catalysts: Dopamine (Anchored On Ferrite),Copper (Nano-Fe-Dopa Supported) Solvents: Dimethylformamide; 18 H,Rt
  标题:Efficient Synthesis Of Alkylboronic Esters Via Magnetically Recoverable Copper Nanoparticle-Catalyzed Borylation Of Alkyl Chlorides And Bromides
  作者:Shegavi,Mahadev L.; Et Al
  参考文献:Green Chemistry 日期:2020 卷标:22(9) 页码:2799-2803]
  
  73183-34-3 = 87100-28-5
  反应条件:1.1 Reagents: Potassium Tert-Butoxide Catalysts: Dopamine (Anchored On Ferrite),Copper (Nano-Fe-Dopa Supported) Solvents: Dimethylformamide; 18 H,Rt
  标题:Efficient Synthesis Of Alkylboronic Esters Via Magnetically Recoverable Copper Nanoparticle-Catalyzed Borylation Of Alkyl Chlorides And Bromides
  作者:Shegavi,Mahadev L.; Et Al
  参考文献:Green Chemistry 日期:2020 卷标:22(9) 页码:2799-2803]
  
  78782-17-9 + 17763-67-6 = 87100-28-5
  反应条件:1.1 Reagents: Tetrabutylammonium Hydroxide Catalysts: Triphenylphosphine,Palladium Diacetate Solvents: 1,4-Dioxane,Water; 1 Min,Rt1.2 3 H,Rt
  标题:Pd-Catalyzed Cross-Coupling Of 1,1-Diborylalkanes With Aryl Triflates
  作者:Cui,Long-Can; Et Al
  参考文献:Rsc Advances 日期:2016 卷标:6(57) 页码:51932-51935]
  
  1632411-83-6 = 87100-28-5
  反应条件:1.1 Catalysts: Ferrous Bromide,Dibromo[1,1′-Oxybis[ethane]]Magnesium Solvents: Tetrahydrofuran; 1 H,Rt
  标题:Iron-Catalyzed Borylation Of Alkyl,Allyl,And Aryl Halides: Isolation Of An Iron(I) Boryl Complex
  作者:Bedford,Robin B.; Et Al
  参考文献:Organometallics 日期:2014 卷标:33(21) 页码:5940-5943]
  
  25015-63-8 + 100-52-7 = 87100-28-5
  反应条件:1.1 Catalysts: 2028324-83-4 Solvents: Diethyl Ether; 16 H,Rt
  标题:Highly Selective Hydroboration Of Alkenes,Ketones And Aldehydes Catalyzed By A Well-Defined Manganese Complex
  作者:Zhang,Guoqi; Et Al
  参考文献:Angewandte Chemie 日期:2016 卷标:55(46) 页码:14369-14372]
  
  76-09-5 = 87100-28-5
  反应条件:1.1 Reagents: 2,2′-Bi-1,3,2-Benzodioxaborole Catalysts: 1H-Indole-1-Carbodithioic Acid,5-Bromo-,Potassium Salt (1:1) Solvents: Dimethylformamide; -78 °C -> Rt; 16 H,Rt1.2 Reagents: Triethylamine; 1 H,Rt
  标题:Photochemical Organocatalytic Borylation Of Alkyl Chlorides,Bromides,And Sulfonates
  作者:Mazzarella,Daniele; Et Al
  参考文献:Acs Catalysis 日期:2019 卷标:9(7) 页码:5876-5880]
  
  100-51-6 + 95843-98-4 = 87100-28-5
  反应条件:1.1 Reagents: Tetrabutylammonium Tetrafluoroborate Solvents: Tetrahydrofuran; 22 °C
  标题:Electrochemically Driven Deoxygenative Borylation Of Alcohols And Carbonyl Compounds
  作者:Guan,Weiyang; Et Al
  参考文献:Journal Of The American Chemical Society 日期:2023 卷标:145(31) 页码:16966-16972]
  
  73183-34-3 = 87100-28-5
  反应条件:1.1 Catalysts: Palladium Solvents: Toluene; 100 °C
  标题:4,4,4',4',5,5,5',5'-Octamethyl-2,2'-Bi-1,3,2-Dioxaborolane
  作者:Ishiyama,Tatsuo; Et Al
  参考文献:E-Eros Encyclopedia Of Reagents For Organic Synthesis 日期:2013 卷标:1 页码:1-13]
  
  14800-24-9 + 73183-34-3 + 37181-39-8 = 87100-28-5
  反应条件:1.1 Reagents: Sodium Tert-Butoxide Catalysts: Bis(1,5-Cyclooctadiene)Nickel,1H-Imidazolium,1,3-Dicyclohexyl-,Chloride (1:1) Solvents: Toluene,Glycol Monoethyl Ether; 12 H,50 °C; 50 °C -> Rt
  标题:Nickel-Catalyzed Borylation Of Aryl- And Benzyltrimethylammonium Salts Via C-N Bond Cleavage
  作者:Hu,Jiefeng; Et Al
  参考文献:Journal Of Organic Chemistry 日期:2016 卷标:81(1) 页码:14-24]
  
  25015-63-8 = 87100-28-5
  反应条件:1.1 Reagents: Triethylamine Catalysts: Magnesium Solvents: 1,2-Dimethoxyethane; 24 H,Reflux1.2 Reagents: Water
  标题:An Opportunity For Mg-Catalyzed Grignard-Type Reactions: Direct Coupling Of Benzylic Halides With Pinacolborane With 10 Mol% Of Magnesium
  作者:Pintaric,Christine; Et Al
  参考文献:Journal Of The American Chemical Society 日期:2010 卷标:132(34) 页码:11825-11827]
  
  76-09-5 + 100-52-7 = 87100-28-5
  反应条件:1.1 Reagents: Water,2,2′-Bi-1,3,2-Benzodioxaborole Solvents: Dimethylacetamide; 12 H,80 °C1.2 Solvents: Triethylamine; 1 H,Rt1.3 Reagents: Sodium Chloride Solvents: Ethyl Acetate,Water
  标题:Metal-Free Direct Deoxygenative Borylation Of Aldehydes And Ketones
  作者:Li,Jianbin; Et Al
  参考文献:Journal Of The American Chemical Society 日期:2020 卷标:142(30) 页码:13011-13020]
  
  73183-34-3 = 87100-28-5
  反应条件:1.1 Reagents: Ethylmagnesium Bromide Catalysts: N,N,N′,N′-Tetramethylethylenediamine,Iron(Iii) Acetylacetonate Solvents: Diethyl Ether,Tetrahydrofuran; Rt; 12 H,Rt
  标题:Iron-Catalyzed Borylation Of Alkyl Electrophiles
  作者:Atack,Thomas C.; Et Al
  参考文献:Journal Of The American Chemical Society 日期:2014 卷标:136(27) 页码:9521-9523]
  
  73183-34-3 = 87100-28-5
  反应条件:1.1 Reagents: Potassium Methoxide Catalysts: Copper Solvents: Dimethylformamide; 1 H,Rt
  标题:Facile Synthesis Of Alkyl- And Arylboronate Esters Enabled By A Carbon Nanotube Supported Copper Catalyst
  作者:Saini,Suresh; Et Al
  参考文献:Catalysis Science & Technology 日期:2023 卷标:13(1) 页码:147-156]
  
  73183-34-3 = 87100-28-5
  反应条件:1.1 Reagents: Tetrabutylammonium Iodide,Potassium Methoxide Catalysts: Copper Solvents: Dimethylformamide; 24 H,80 °C
  标题:Facile Synthesis Of Alkyl- And Arylboronate Esters Enabled By A Carbon Nanotube Supported Copper Catalyst
  作者:Saini,Suresh; Et Al
  参考文献:Catalysis Science & Technology 日期:2023 卷标:13(1) 页码:147-156]
  
  1632411-83-6 = 87100-28-5
  反应条件:1.1 Catalysts: Ferrous Bromide,Dibromo[1,1′-Oxybis[ethane]]Magnesium Solvents: Tetrahydrofuran; 1 H,Rt
  标题:Iron-Catalyzed Borylation Of Alkyl,Allyl,And Aryl Halides: Isolation Of An Iron(I) Boryl Complex
  作者:Bedford,Robin B.; Et Al
  参考文献:Organometallics 日期:2014 卷标:33(21) 页码:5940-5943]
  
  100-51-6 + 25015-63-8 = 87100-28-5
  反应条件:1.1 Reagents: Tetrabutylammonium Tetrafluoroborate Solvents: 1,2-Dimethoxyethane; 22 °C
  标题:Electrochemically Driven Deoxygenative Borylation Of Alcohols And Carbonyl Compounds
  作者:Guan,Weiyang; Et Al
  参考文献:Journal Of The American Chemical Society 日期:2023 卷标:145(31) 页码:16966-16972]
  
  76-09-5 + 100-51-6 = 87100-28-5
  反应条件:1.1 Reagents: 2,2′-Bi-1,3,2-Benzodioxaborole Catalysts: Iodine Solvents: N-Methyl-2-Pyrrolidone; 12 H,120 °C; 120 °C -> Rt1.2 Reagents: Triethylamine; 1 H,Rt
  标题:Iodine-Catalyzed Borylation Of Benzylic Alcohols
  作者:Yin,Chunyu; Et Al
  参考文献:Organic Letters 日期:2023 卷标:25(10) 页码:1701-1705]
  
  25015-63-8 = 87100-28-5
  反应条件:1.1 Reagents: Pinacolborane Catalysts: Ceria (Supports Nickel Hydroxide),Nickel Hydroxide (Cerium Oxide Supported) Solvents: Cyclopentyl Methyl Ether; 30 Min,100 °C1.2 Solvents: Methylcyclohexane; 20 H,100 °C
  标题:C(Sp3)-H Selective Benzylic Borylation By In Situ Reduced Ultrasmall Ni Species On Ceo2
  作者:Yoshii,Daichi; Et Al
  参考文献:Acs Catalysis 日期:2021 卷标:11(4) 页码:2150-2155]
  
  25015-63-8 = 87100-28-5
  反应条件:1.1 Catalysts: (Sp-4-3)-Chloro(Dinitrogen)Bis[tris(1-Methylethyl)Phosphine]Rhodium; 140 °C
  标题:Pinacolborane
  作者:Ramachandran,P. Veeraraghavan; Et Al
  参考文献:E-Eros Encyclopedia Of Reagents For Organic Synthesis 日期:2014 卷标:1 页码:1-7]
  
  25015-63-8 = 87100-28-5 [标题:Reaction Conditions
  标题:Product Subclass 34: Benzylboranes And Benzylboronates
  作者:Zaidlewicz,M.; Et Al
  参考文献:Science Of Synthesis 日期:2004 卷标:6 页码:921-943]
  
  25015-63-8 + 100-52-7 = 87100-28-5
  反应条件:1.1 Reagents: Tetrabutylammonium Tetrafluoroborate Solvents: Tetrahydrofuran; 22 °C
  标题:Electrochemically Driven Deoxygenative Borylation Of Alcohols And Carbonyl Compounds
  作者:Guan,Weiyang; Et Al
  参考文献:Journal Of The American Chemical Society 日期:2023 卷标:145(31) 页码:16966-16972]
  
  76-09-5 + 63591-85-5 = 87100-28-5
  反应条件:1.1 Reagents: 2,2′-Bi-1,3,2-Benzodioxaborole Solvents: Dimethylacetamide; 14 H1.2 Reagents: Triethylamine; 1 H1.3 Reagents: Ammonium Chloride Solvents: Ethyl Acetate,Water
  标题:Photoinduced Decarboxylative Borylation Of Carboxylic Acids
  作者:Fawcett,Alexander; Et Al
  参考文献:Science (Washington 日期:2017 卷标:357(6348) 页码:283-286]
  
  76-09-5 = 87100-28-5
  反应条件:1.1 Reagents: Sodium Methoxide,2,2′-Bi-1,3,2-Benzodioxaborole Catalysts: 4-Phenylpyridine Solvents: Acetonitrile; 24 H,Rt1.2 Reagents: Triethylamine; 1 H,Rt1.3 Solvents: Ethyl Acetate,Water; Rt
  标题:Photoinduced Radical Borylation Of Alkyl Bromides Catalyzed By 4-Phenylpyridine
  作者:Zhang,Li; Et Al
  参考文献:Angewandte Chemie 日期:2020 卷标:59(5) 页码:2095-2099]
  
  18645-12-0 + 24388-23-6 = 87100-28-5
  反应条件:1.1 Solvents: Tetrahydrofuran
  标题:Homologation Of Representative Boronic Esters Using In Situ Generated (Halomethyl)Lithiums: A Comparative Study
  作者:Soundararajan,Raman; Et Al
  参考文献:Tetrahedron Letters 日期:1994 卷标:35(48) 页码:8957-60]
  
  73183-34-3 = 87100-28-5
  反应条件:1.1 Catalysts: Pinacolborane,[n,N′-(1,2-Dimethyl-1,2-Ethanediylidene)Bis[cyclohexanamine-κn]]Bis(2-Ethylhexan... Solvents: Cyclopentyl Methyl Ether; 16 H,100 °C; 100 °C -> 23 °C1.2 Reagents: Oxygen
  标题:Cobalt-Catalyzed Benzylic Borylation: Enabling Polyborylation And Functionalization Of Remote,Unactivated C(Sp3)-H Bonds
  作者:Palmer,W. Neil; Et Al
  参考文献:Journal Of The American Chemical Society 日期:2016 卷标:138(3) 页码:766-769]
  
  73183-34-3 = 87100-28-5
  反应条件:1.1 Catalysts: Palladium
  标题:Palladium-Catalyzed Benzylic C-H Borylation Of Alkylbenzenes With Bis(Pinacolato)Diboron Or Pinacolborane
  作者:Ishiyama,Tatsuo; Et Al
  参考文献:Chemistry Letters 日期:2001 卷标:(11) 页码:1082-1083]
  
  98-80-6 + 76-09-5 + 18107-18-1 = 87100-28-5
  反应条件:1.1 Solvents: Hexane,1,4-Dioxane; 4 H,50 °C1.2 Reagents: Tetrabutylammonium Fluoride Solvents: Tetrahydrofuran,1,4-Dioxane,Water; 4 H,50 °C
  标题:One-Carbon Homologation Of Arylboronic Acids: A Convenient Approach To The Synthesis Of Pinacol Benzylboronates
  作者:Wu,Chaoqiang; Et Al
  参考文献:Organic Chemistry Frontiers 日期:2016 卷标:3(7) 页码:817-822]
  
  14800-24-9 + 73183-34-3 + 37181-39-8 = 87100-28-5
  反应条件:1.1 Reagents: Sodium Tert-Butoxide Catalysts: Tributylphosphine,Nickel Nitrate Solvents: 1,2-Dimethoxyethane; 24 H,70 °C
  标题:Making Dimethylamino A Transformable Directing Group By Nickel-Catalyzed C-N Borylation
  作者:Zhang,Hua; Et Al
  参考文献:Chemistry - A European Journal 日期:2015 卷标:21(47) 页码:16796-16800]
  
  25015-63-8 = 87100-28-5
  反应条件:1.1 Reagents: Lithium Bis(Trifluoromethanesulfonyl)Imide Solvents: Tetrahydrofuran; Rt1.2 Solvents: Water; Rt
  标题:Electrosynthesis Of Benzylboronic Acids And Esters
  作者:Pintaric,C.; Et Al
  参考文献:Tetrahedron Letters 日期:2004 卷标:45(43) 页码:8031-8033]
  
  4463-42-7 + 166330-03-6 = 87100-28-5
  反应条件:1.1 Reagents: Tripotassium Phosphate Catalysts: Tetrakis(Triphenylphosphine)Palladium Solvents: Toluene,Water; Rt -> 60 °C; 24 H,60 °C
  标题:Pd-Catalyzed Organometallic-Free Homologation Of Arylboronic Acids Enabled By Chemoselective Transmetalation
  作者:Bastick,Kane A. C.; Et Al
  参考文献:Acs Catalysis 日期:2023 卷标:13(10) 页码:7013-7018

海关参考信息

• 2902300000-甲苯
  2905122000-异丙醇
  2905143000-叔丁醇
  2905310000-1,2-乙二醇
• 💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
• 详情请参考：📖 海关编码查询和海关进出口税则

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