(3-nitrophenyl)boronic acid

• ChemBase编号: 2511
• 分子式: C6H6BNO4
• 平均质量: 166.92714
• 单一同位素质量: 167.03898808
• SMILES: OB(O)c1cccc(c1)[N+](=O)[O-]
• Canonical SMILES: OB(c1cccc(c1)[N+](=O)[O-])O
• InChI: InChI=1S/C6H6BNO4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4,9-10H
• InChIKey: ZNRGSYUVFVNSAW-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: (3-nitrophenyl)boronic acid
• IUPAC传统名: β-(3-nitrophenyl)-boronic acid; 3-nitrophenylboronic acid
• 别名: 间硝基苯硼酸; 3-硝基苯硼酸; 3-Nitrobenzeneboronic acid; (3-nitrophenyl)boranediol; 3-Nitrophenylboronic Acid; m-Nitrobenzeneboronic acid; m-Nitrophenylboronic acid; NSC 401539; NSC 59739; 3-Nitrobenzeneboronic acid; 3-Nitrophenylboronic acid; 3-Nitrophenylboronic acid; 3-Nitrophenylboric acid; 3-Nitrobenzeneboronic acid

登记号

• CAS号: 13331-27-6
• MDL号: MFCD00007193
• Beilstein号: 2938638
• PubChem SID: 46507867; 24859487; 160965961
• PubChem CID: 1677

理论计算性质

JChem

• Acid pKa: 8.387791
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 1.5928411
• LogD (pH = 7.4): 1.5511011
• Log P: 1.5934
• 摩尔折射率: 36.924 cm^3
• 极化性: 15.466121 Å^3
• 极化表面积: 83.6 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.52
• LOG S: -2.08
• 溶解度: 1.40e+00 g/l

分子性质

理化性质

• 熔点: 284 - 285°C; 284-285 °C (dec.)(lit.); 288-290°C; 289-291°C; ca 285°C dec.
• 疏水性(logP): 1.338

安全信息

• 保存注意事项: Harmful; Hygroscopic; IRRITANT
• RTECS编号: CY8980000
• 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; 26-37/39
• TSCA收录: true; 是
• 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: ≥97%; 95%; 97%; 98%
• 线性分子式: O2NC6H4B(OH)2

详细说明

DrugBank - DB02797

Drug information: experimental

Sigma Aldrich - 325104

Application
催化炔二羰基化合物的烯碳环化反应8
Reactant involved in:
• Copper-catalyzed arylation1
• Palladium-catalyzed decarboxylative coupling2
• Suzuki-Miyaura cross-coupling3
• Oxidative carbocyclization / arylation4
• Addition to arylpropargyl alcohols5Additionally used as a reactant for synthesizing biologically active molecules such as:
• Inhibitors of angiogenesis6
• Biaryl-olefins with antiproliferative activities7
Other Notes
含不定量的酸酐
包装
1, 5 g in glass bottle

参考文献

• Reagent for derivatization of diols and diamines for GC: Chromatographia, 11, 347 (1978).
• Oxidative conversion of arylboronic acids to phenols with potassium monopersulfate in buffered aqueous acetone (in situ dimethyldioxirane) is exemplified for this compound: Tetrahedron Lett., 36, 5117 (1995).
• Mild Lewis acid catayst, for example in the selective transesterification of ?-keto esters: Synlett, 415 (2006). See also 3,4,5-Trifluorobenzeneboronic acid, L18519. For reactions of boronic acids, see Appendix 5.