(4-cyanophenyl)boronic acid

• ChemBase编号: 7928
• 分子式: C7H6BNO2
• 平均质量: 146.93904
• 单一同位素质量: 147.04915884
• SMILES: c1c(ccc(c1)B(O)O)C#N
• Canonical SMILES: N#Cc1ccc(cc1)B(O)O
• InChI: InChI=1S/C7H6BNO2/c9-5-6-1-3-7(4-2-6)8(10)11/h1-4,10-11H
• InChIKey: CEBAHYWORUOILU-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: (4-cyanophenyl)boronic acid
• IUPAC传统名: 4-cyanophenylboronic acid
• 别名: 4-氰基苯硼酸; 4-(dihydroxyboranyl)benzonitrile; (4-cyanophenyl)boronic acid; 4-Cyanophenylboronic acid; 4-Cyanobenzeneboronic acid; (p-Cyanophenyl)boronic acid; 4-Cyanobenzeneboronic acid; 4-Cyanophenylboric acid; 4-Cyanophenylboronic acid; 4-Boronobenzonitrile; 4-Cyanobenzeneboronic acid; 4-Cyanophenylboronic acid

登记号

• CAS号: 126747-14-6
• MDL号: MFCD01318968
• Beilstein号: 6593772
• PubChem SID: 24874205; 160971235
• PubChem CID: 2734326

理论计算性质

• Acid pKa: 8.655867
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 1.4544984
• LogD (pH = 7.4): 1.4314744
• Log P: 1.4548
• 摩尔折射率: 36.3251 cm^3
• 极化性: 15.363086 Å^3
• 极化表面积: 64.25 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: >300°C; >350 °C(lit.); >350°C; 300 - 302°C
• 疏水性(logP): 1.028

安全信息

• 保存注意事项: Irritant; KEEP COLD
• 欧盟危险性物质标志: X
• 德国WGK号: 3
• 危险公开号: 22-36/37/38
• 安全公开号: 26-36/37
• TSCA收录: false; 否
• GHS危险品标识: GHS06
• GHS危险声明: H301-H315-H319-H335
• GHS警示性声明: P261-P301+P310-P305+P351+P338-P302+P352-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: NCC6H4B(OH)2

详细说明

Sigma Aldrich - 521418

Other Notes
含有不定量的酸酐
包装
1 g in glass bottle
10 g in poly bottle
Application
Reactant involved in:
• Oxidative hydroxylation1
• Trifluoromethylation2
• 1,4-Addition reactions3Precursor in the synthesis of inhibitors such as:
• Tpl2 kinase inhibitors4
• P2X7 antagonists used in the treatment of pain5
Reagent used for
• Palladium-catalyzed arylation Suzuki-Miyaura cross-coupling in water
• Ruthenium catalyzed direct arylation of benzylic sp3 carbons of acyclic amines with arylboronates
• Ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids
• Ferric perchlorate-promoted reaction of fullerenes with various arylboronic acids to give fullerenyl boronic esters
• Phosphine-free Suzuki-Miyaura cross-coupling
• Palladacycles as effective catalysts for multicomponent reaction with allylpalladium-intermediates
• Chan-Lam-type Cu-catalyzed S-arylation of thiols
• Regioselective cross-coupling reactions under modfied Suzuki and Still cross-coupling reactions with Copper catalysis
• Metal-free biaryl coupling in dimethyl carbonate as a solventReagent used for Preparation of
• Himbacine analogs as thrombin receptor antagonists and potential antiplatelet agents
• Trisulfonated calixarene upper-rim sulfonamido and their complexation with trimethyllysine epigenetic mark
• Antimalarial compounds via Suzuki cross-coupling
• Deoxyuridine derivatives