Pinacol borane 频那醇硼烷

CAS 25015-63-8 MFCD00674030

化学结构图

25015-63-8
SMILES: CC1(C)O[B]OC1(C)C

化学属性

Mol. FormulaC6H13BO2
Mol. Weight127.98
Boiling Point42-43 °C at 50 mmHg
Density0.887
Refractive index1.3940 to 1.3980
Flash Point5°C(lit.)
TSCANo
pH:A

别名和识别编码

Chemical NamePinacol borane
CAS Number25015-63-8
Synonym 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane {LY} 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane {} {LY} 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane {} {} {LY} 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane {} {} {} {LY} 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane {} {} {} {} {LY} 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane {} {} {} {} {} {LY} 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane {} {} {} {} {} {} {LY} 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane {} {} {} {} {} {} {} {LY} 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane {} {} {} {} {} {} {} {} {LY} 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane {} {} {} {} {} {} {} {} {} {LY} 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane {} {} {} {} {} {} {} {} {} {} {LY} 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane {} {} {} {} {} {} {} {} {} {} {} {LY} 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane {} {} {} {} {} {} {} {} {} {} {} {} {LY} 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 4,4,5,5-Tetramethyl-1,3,2-dioxaborol
PubChem Substance ID6364989
MDL NumberMFCD00674030
Beilstein Registry Number7802871
EC Number250-023-7
Reaxys-RN7802871
Chemical Name Translation频那醇硼烷
InChIKeyLZPWAYBEOJRFAX-UHFFFAOYSA-N
LabNetwork Molecule IDLN00008800
InChIInChI=1S/C6H12BO2/c1-5(2)6(3,4)9-7-8-5/h1-4H3
Canonical SMILESCC1(C)C(C)(C)OBO1
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分类

  • {SNA} Boronic Acids and Derivatives, Borylation Reagents, Chemical Synthesis, Organometallic Reagents
  • {SNA} 25mL Sure/Seal Reagents, Boronic Acids and Derivatives, Borylation Reagents, Chemical Synthesis, Organometallic Reagents
  • Heterocycles
  • Boron Derivatives

产品应用

  • It is used for synthesis of unsymmetrical biaryls via aromatic C-H borylation-cross-coupling sequence.

相关文献及参考

  • Coupling aryl iodides and bromides, catalyzed by [1,1'-Bis(diphenyl­phosphino)­ferrocene]palladium(II)­ chloride, 41225, gives the aryl pinacolboronates: J. Org. Chem., 62, 6458 (1997); 65, 164 (2000). In the presence of triphenylarsine, Pd-catalyzed coupling with alkenyl triflates and iodides affords vinylboronates: Synthesis, 778 (2000). For a brief review of uses of pinacolborane, see: Synlett, 1210 (2000).
  • Precursor of boronic esters by hydroboration or coupling reactions. Hydroboration of alkynes, in the presence of Rh or Ni catalysts, yields alkenylboronates: Tetrahedron Lett., 37, 3283 (1996). Hydroboration of alkenes in the presence of Chlorotris(triphenyl­phosphine)­rhodium(I)­, 10468, affords the alkylboronate: Tetrahedron Lett., 37, 3283 (1996); with phosphine-free catalyst Chloro(1,5-cyclooctadiene)­rhodium(I)­ dimer, 10466, dehydrogenative borylation predominates to give the alkenylboronate: Tetrahedron Lett., 40, 213 (1999); Bull. Chem. Soc. Jpn., 75, 825 (2002):

安全信息

GHS Symbol
WGK Germany3
Hazard statements
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
  • H261 In contact with water releases flammable gas 与水接触时释放可燃气体。
  • H351 Suspected of causing cancer 怀疑致癌
  • H302 Harmful if swallowed 吞食有害
Personal Protective Equipment Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
Precautionary statements
  • P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 远离热源/火花/明火/热的表面。——禁止吸烟。
  • P223 Keep away from any possible contact with water, because of violent reaction and possible flash fire. 远离任何与水接触的可能,因为会剧烈反应可能产生闪火。
  • P231+P232
  • P233 Keep container tightly closed. ?保持容器密闭。
  • P240 Ground/bond container and receiving equipment. 与地面接触/连接集装箱和接受设备。
  • P241+P242+P243
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P303+P361+P353
  • P305+P351+P338
  • P335+P334
  • P370+P378
  • P402+P404
  • P403+P235
  • P422 Store contents under… 存储目录在…之下。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Signal word Danger
Packing GroupII
UN Number 3398 3399
Risk Statements
  • R11 Highly flammable 非常易燃
  • R15 Contact with water liberates extremely flammable gases 遇水会释放出极端易燃的气体
  • R19 May form explosive peroxides 可能生成易爆的过氧化物质
  • R36/37 Irritating to eyes and respiratory system 对眼睛和呼吸系统有刺激性
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
Safety Statements
  • S16 Keep away from sources of ignition - No smoking 远离火源,禁止吸烟;
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套;
  • S43 In case of fire use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add -?Never use water) 着火时使用(指明具体的消防器材种类,如果用水增加危险,注明“禁止用水”
Storage condition 2-8°C {LY} 2-8°C Air Sensitive {} {LY} 2-8°C {} {} {LY} 2-8°C {} {} {} {LY} 2-8°C {} {} {} {} {LY} 2-8°C {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
Hazard Codes 4.3 F F,Xn
Hazard Class4.3/3

系列性分类


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