2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

• ChemBase编号: 139800
• 分子式: C8H15BO2
• 平均质量: 154.0145
• 单一同位素质量: 154.11651012
• SMILES: B1(OC(C(O1)(C)C)(C)C)C=C
• Canonical SMILES: C=CB1OC(C(O1)(C)C)(C)C
• InChI: InChI=1S/C8H15BO2/c1-6-9-10-7(2,3)8(4,5)11-9/h6H,1H2,2-5H3
• InChIKey: DPGSPRJLAZGUBQ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• IUPAC传统名: 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 别名: 2-乙烯基-4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷; 乙烯基硼酸频哪醇酯; 2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 2-Vinyl-4,4,5,5-tetramethyl-1,3,2-dioxaoborolane; 4,4,5,5-Tetramethyl-2-vinyl-1,3,2-dioxaborolane; Vinylboronic acid pinacol ester; VINYLBORONIC ACID PINACOL ESTER

登记号

• CAS号: 75927-49-0
• MDL号: MFCD00192492
• PubChem SID: 162234048; 24882546
• PubChem CID: 5233012

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 2.8193
• LogD (pH = 7.4): 2.8193
• Log P: 2.8193
• 摩尔折射率: 39.7211 cm^3
• 极化性: 17.865597 Å^3
• 极化表面积: 18.46 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

• 闪点: 34 °C; 93.2 °F
• 密度: 0.908 g/mL at 25 °C(lit.)
• 折射率: n20/D 1.4300(lit.)

安全信息

• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 联合国危险货物编号: 3272
• 德国WGK号: 3
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 10-43
• 安全公开号: 36/37
• GHS危险品标识: GHS02; GHS07
• GHS警示词: Warning
• GHS危险声明: H226-H317
• GHS警示性声明: P280
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3272 3/PG 3
• 保存温度: -20°C

产品相关信息

• 纯度: 95%; 98%
• 其他组分: phenothiazine as stabilizer
• Empirical Formula (Hill Notation): C8H15BO2

详细说明

Sigma Aldrich - 633348

包装
1, 10 g in glass bottle
Application
Reagent used for
• Suzuki-Miyaura coupling reactions1
• Mizoroki-Heck reactions (cascade reaction)1
• Intramolecular Nozaki-Hiyama-Kishi reactions2
• Stereoselective Cu-catalyzed γ-selective and stereospecific coupling3
• Control of stereoselectivity and mechanistic portrait on intramolecular (4+1)-cycloaddition of dialkoxycarbenes4
• Regio- and stereoselective synthesis of trisubstituted alkenes via gold(I)-catalyzed hydrophosphoryloxylation of haloalkynes followed by Pd-catalyzed consecutive cross-coupling reactions5
• Asymmetric Birch reductive alkylation6Reagent used in Preparation of
• Molecular tubes for lipid sensing7
• Enzymatic inhibitors, antibiotics, receptor analogs, and other biologically significant compounds (including total syntheses)8,9,10,2