(3,4,5-trifluorophenyl)boronic acid

• ChemBase编号: 12425
• 分子式: C6H4BF3O2
• 平均质量: 175.9009696
• 单一同位素质量: 176.02564443
• SMILES: c1(c(c(cc(c1)B(O)O)F)F)F
• Canonical SMILES: OB(c1cc(F)c(c(c1)F)F)O
• InChI: InChI=1S/C6H4BF3O2/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,11-12H
• InChIKey: UHDDEIOYXFXNNJ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: (3,4,5-trifluorophenyl)boronic acid
• IUPAC传统名: 3,4,5-trifluorophenylboronic acid
• 别名: 3,4,5-三氟苯硼酸; 3,4,5-Trifluorophenylboronic acid; 3,4,5-Trifluorobenzeneboronic acid; 3,4,5-Trifluorophenylboronic acid; 3,4,5-Trifluorobenzeneboronic acid 97%; (3,4,5-Trifluorophenyl)boronic acid; 3,4,5-Trifluorophenylboronic acid; 3,4,5-Trifluorobenzeneboronic acid; (3,4,5-trifluorophenyl)boranediol

登记号

• CAS号: 143418-49-9
• EC号: 000-000-0
• MDL号: MFCD02093069
• Beilstein号: 7371914
• PubChem SID: 160975732; 24874437
• PubChem CID: 2734671

理论计算性质

• Acid pKa: 8.491755
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): 2.05786
• LogD (pH = 7.4): 2.0246685
• Log P: 2.0583
• 摩尔折射率: 31.2527 cm^3
• 极化性: 12.921739 Å^3
• 极化表面积: 40.46 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: 275-279°C; 275-279°C; 290-295 °C(lit.); 295 - 297°C
• 疏水性(logP): 1.884

安全信息

• 保存注意事项: IRRITANT; Irritant/Store under Argon/Keep Cold
• 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: 26-37
• TSCA收录: false; 否
• GHS危险品标识: GHS07
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: 95%; 97%; 98%
• 线性分子式: F3C6H2B(OH)2

详细说明

Apollo Scientific Ltd - PC4336

Very reactive catalyst to produce amides in high yieldsfrom carboxylic acids and primary or secondary aminesJ. Org. Chem., 61, 4196 (1996)

Sigma Aldrich - 524700

Other Notes
含有不定量的酸酐。
包装
1, 5 g in glass bottle
Application
Reactant involved in:
• Preparation of phenylboronic catechol esters and determination of Lewis acidity1
• Synthesis of benzopyranone derivatives as GABAA receptor modulators2
• Synthesis of multisubstituted olefins and conjugate dienes3
• Suzuki cross-coupling reactions4,5
• Preparation of fluorinated aromatic poly(ether-amide)s6

参考文献

• Extremely active catalyst for the reaction of carboxylic acids with primary and secondary amines to give the corresponding amides in very high yields: J. Org. Chem., 61, 4196 (1996). Also useful in the one-pot synthesis of acyl azides from carboxylic acids and NaN₃: Tetrahedron Lett.,43, 9715 (2002). Mediates the mild, one-pot reduction of carboxylic acids to alcohols with NaBH₄: Tetrahedron Lett., 44, 3427 (2003).
• For other boronic acid chemistry, see Appendix 5.