(2H-1,3-benzodioxol-5-yl)boronic acid

• ChemBase编号: 8562
• 分子式: C7H7BO4
• 平均质量: 165.93908
• 单一同位素质量: 166.0437391
• SMILES: c1c(ccc2c1OCO2)B(O)O
• Canonical SMILES: OB(c1ccc2c(c1)OCO2)O
• InChI: InChI=1S/C7H7BO4/c9-8(10)5-1-2-6-7(3-5)12-4-11-6/h1-3,9-10H,4H2
• InChIKey: CMHPUBKZZPSUIQ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: (2H-1,3-benzodioxol-5-yl)boronic acid
• IUPAC传统名: 2H-1,3-benzodioxol-5-ylboronic acid
• 别名: 3,4-(亚甲基二氧基)苯硼酸; 3,4-亚甲二氧基苯硼酸; 3,4-Methylenedioxybenzeneboronic acid; 1,3-Benzodioxole-5-boronic acid; 1,3-benzodioxol-5-ylboronic acid; 1,3-Benzodioxole-5-boronic acid; 3,4-(Methylenedioxy)phenylboronic acid; 3,4-Methylenedioxyphenylboronic acid; 3,4-(Methylenedioxy)phenylboronic acid; 3,4-(Methylenedioxy)benzeneboronic acid

登记号

• CAS号: 94839-07-3
• MDL号: MFCD01009695
• Beilstein号: 5523347
• PubChem SID: 160971869; 24873316
• PubChem CID: 2734371

理论计算性质

• Acid pKa: 8.755093
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 1.32386
• LogD (pH = 7.4): 1.3054383
• Log P: 1.3241
• 摩尔折射率: 36.3704 cm^3
• 极化性: 16.038465 Å^3
• 极化表面积: 58.92 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: 224-229 °C(lit.); 224-229°C; 239-243°C; 243-245°C

安全信息

• 保存注意事项: IRRITANT; 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: 26-37
• 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: 97%; 98%
• Empirical Formula (Hill Notation): C7H7BO4

详细说明

Sigma Aldrich - 499994

Other Notes
含有不定量的酸酐
包装
1, 5 g in glass bottle
Application
Reactant involved in:
• Petasis reaction between glyoxylic acid, α-amino phosphonates, and organylboronic acids1
• Mannich-type multicomponent assembly and 1,3-dipolar cycloaddition for synthesis of tetrahydroisoquinoline fused isoxazolidine scafford2
• Suzuki-Miyaura cross-coupling of aryl and heteroaryl halides3,4
• Oxidative Heck reaction for synthesis of functionalized cinnamaldehyde derivatives5
• Intramolecular Alder-ene and Pictet-Spengler reactions for synthesis of crinine6

参考文献

• Suzuki coupling (Appendix 5) with 1-amino-2-bromonaphthalene derivatives has been used in a versatile synthesis of benzo[c]phenanthridine alkaloids: J. Chem. Soc., Perkin 1, 1647 (1996).