potassium trifluoro(phenyl)boranuide

• ChemBase编号: 93979
• 分子式: C6H5BF3K
• 平均质量: 184.0084096
• 单一同位素质量: 184.0073469
• SMILES: [B-](c1ccccc1)(F)(F)F.[K+]
• Canonical SMILES: F[B-](c1ccccc1)(F)F.[K+]
• InChI: InChI=1S/C6H5BF3.K/c8-7(9,10)6-4-2-1-3-5-6;/h1-5H;/q-1;+1
• InChIKey: DVAFPKUGAUFBTJ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: potassium trifluoro(phenyl)boranuide
• IUPAC传统名: potassium ion trifluoro(phenyl)boranuide; potassium trifluoro(phenyl)boranuide
• 别名: 苯基三氟硼酸钾; Potassium phenyltrifluoroborate; Potassium phenyltrifluoroborate; Potassium trifluoro(phenyl)borate; Benzenetrifluoroboric acid potassium salt; Phenyltrifluoroboric acid potassium salt

登记号

• CAS号: 153766-81-5
• EC号: 000-000-0
• MDL号: MFCD01318172
• Beilstein号: 7782070
• PubChem SID: 24880142; 162080634
• PubChem CID: 23675248

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 2.1297
• LogD (pH = 7.4): 2.1297
• Log P: 2.1297
• 摩尔折射率: 29.9782 cm^3
• 极化性: 11.8859 Å^3
• 极化表面积: 0.0 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 296-301°C; 296-301°C

安全信息

• 保存注意事项: Irritant
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36; 26-37
• TSCA收录: 否
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: 95%; 95+%; 98%
• Empirical Formula (Hill Notation): C6H5BF3K

详细说明

Sigma Aldrich - 563951

包装
1, 5 g in poly bottle
Protocols & Applications
Suzuki Cross-Coupling using Organotrifluoroborates as Potent Boronic Acid Surrogates

参考文献

• Treatment with TMS chloride in acetonitrile generates the Lewis acid phenylboron difluoride in situ, avoiding the need to handle boron trihalides: J. Org. Chem., 60, 3020 (1995).
• Aryltrifluoroborate salts are more nucleophilic than the corresponding arylboronic acids and undergo ligand-free Pd-catalyzed cross-coupling reactions with arenediazonium tetrafluoroborates to give good yields of biaryls: Tetrahedron Lett., 38, 4393 (1997); Eur. J. Org. Chem., 1875 (1999). Cross-coupling with aryl or heteroaryl halides and triflates, under ligand-free conditions, has subsequently been reported: Org. Lett., 4, 1867 (2002).
• Coupling with diaryliodonium salts has also been reported: Synth. Commun., 29, 2457 (1999). The method has been extended to the synthesis of benzophenones by carbonylative cross-coupling in the presence of CO: J. Chem. Res. (Synop.), 400 (1999).
• In the presence of Dicarbonyl(2,4-pentanedionato)rhodium(I), 39295, K aryl- and alkenyltrifluoroborates add to aldehydes and enones to give secondary alcohols and saturated ketones, respectively: Org. Lett., 1, 1683 (1999):
  
• Asymmetric Rh-catalyzed additions to enones in the presence of a chiral BINAP catalyst give the corresponding saturated ketones in high yield and ee: Eur. J. Org. Chem., 3552 (2002).