(thiophen-2-yl)boronic acid

• ChemBase编号: 6669
• 分子式: C4H5BO2S
• 平均质量: 127.9573
• 单一同位素质量: 128.0103308
• SMILES: c1(sccc1)B(O)O
• Canonical SMILES: OB(c1cccs1)O
• InChI: InChI=1S/C4H5BO2S/c6-5(7)4-2-1-3-8-4/h1-3,6-7H
• InChIKey: ARYHTUPFQTUBBG-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: (thiophen-2-yl)boronic acid
• IUPAC传统名: thiophen-2-ylboronic acid
• 别名: 2-噻吩硼酸; 噻吩-2-硼酸; 2-噻吩硼酸; 噻酚-2-硼酸; Thiophen-2-ylboronic acid; Thiophene-2-boronic acid; 2-thienylboronic acid; 2-Thienylboric acid; Thien-5-ylboronic acid; 2-Thienylboronic acid; Thiophene-2-boronic acid; 2-Thienylboronic acid; 2-Thiopheneboronic acid; Thiophene-2-boronic acid; thiophen-2-ylboranediol; 2-Boronothiophene

登记号

• CAS号: 6165-68-0
• EC号: 000-000-0
• MDL号: MFCD00151850
• Beilstein号: 112375
• PubChem SID: 160969976; 24867305
• PubChem CID: 2733960

理论计算性质

• Acid pKa: 7.984538
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): 1.2322869
• LogD (pH = 7.4): 1.1336635
• Log P: 1.2337
• 摩尔折射率: 26.8692 cm^3
• 极化性: 12.232995 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: 128-131°C; 128-131°C; 138-140 °C(lit.); 138-140°C; 139 - 140°C
• 疏水性(logP): 1.241

安全信息

• 保存注意事项: Harmful/Irritant/Keep Cold; IRRITANT, KEEP COLD
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi); 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-36/37/38; 36/37/38
• 安全公开号: 26-36/37; 26-37
• TSCA收录: false; 否
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H315-H319-H335; 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
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥95.0%; 95%; 97%; 98%
• Empirical Formula (Hill Notation): C4H5BO2S

详细说明

Sigma Aldrich - 436836

Other Notes
含有不定量的酸酐
包装
1, 5 g in glass bottle
Application
Reagent used for
• Palladium-catalyzed Suzuki-Miyaura cross-couplings1
• Alkylation, boration, coupling reaction, Suzuki coupling, and halogenation of fluorenyl bromide2
• Chain-growth catalyst transfer polycondensation of conjugated alternating copolymer3
• Ferric perchlorate-promoted reaction of fullerene to give fullerenyl boronic esters4
• Ligand-free Suzuki, Sonogashira, and Heck cross-coupling reactions5
• Copper-catalyzed nitration reactions6
• Geometry relaxation-induced Large Stokes shift in red-emitting borondipyrromethenes (BODIPY) and applications in fluorescent thiol probes7 Reagent used in Preparation of
• Photophysical properties of oxygen-containing polycyclic aromatic triptycenes8
• Donor unit for donor-acceptor-type polymers via N-alkylation, Suzuki coupling, and bromination9
• Aminopyridine-based inhibitors of mitotic kinase Nek2 with potential antipoliferative effects in cancer tumors10

参考文献

• Suzuki coupling (see Appendix 5) to a polymer-bound aryl iodide gives the 2-arylthiophene derivative in high yield: J. Org. Chem., 61, 5169 (1996).