4,4,5,5-tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolane

• ChemBase编号: 63858
• 分子式: C9H17BO2
• 平均质量: 168.04108
• 单一同位素质量: 168.13216018
• SMILES: B1(OC(C(O1)(C)C)(C)C)CC=C
• Canonical SMILES: C=CCB1OC(C(O1)(C)C)(C)C
• InChI: InChI=1S/C9H17BO2/c1-6-7-10-11-8(2,3)9(4,5)12-10/h6H,1,7H2,2-5H3
• InChIKey: YMHIEPNFCBNQQU-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4,4,5,5-tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolane
• IUPAC传统名: 4,4,5,5-tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolane
• 别名: 2-烯丙基-4,4,5,5-四甲基-1,3,2-二氧环戊硼烷; 丙烯基硼酸频哪醇酯; 烯丙基硼酸频哪醇酯; 丙烯基硼酸邻二叔醇酯; Allylboronic acid, pinacol cyclic ester; 2-(Prop-2-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; Allylboronic acid, pinacol ester; 4,4,5,5-tetramethyl-2-(2-propen-1-yl)-1,3,2-dioxaborolane; 4,4,5,5-tetramethyl-2-(2-propenyl)-1,3,2-dioxaborolane; Allyl pinacol boronate; Pinacolyl 2-propenylboronate; 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; Pinacol allylboronate; Allylboronic acid pinacol ester; ALLYLBORONIC ACID PINACOL ESTER

登记号

• CAS号: 72824-04-5
• MDL号: MFCD00013347
• Beilstein号: 4244068
• PubChem SID: 24859457; 162029597
• PubChem CID: 2763171

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 2.8201
• LogD (pH = 7.4): 2.8201
• Log P: 2.8201
• 摩尔折射率: 45.2642 cm^3
• 极化性: 19.709911 Å^3
• 极化表面积: 18.46 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 沸点: 50-53 °C/5 mmHg(lit.); 50-53°C/5mm; 50-53°C/5mm
• 闪点: 114.8 °F; 46 °C; 46°C; 60°C(140°F)
• 密度: 0.890; 0.896; 0.896 g/mL at 25 °C(lit.)
• 折射率: 1.4270; n20/D 1.4268(lit.)

安全信息

• 保存注意事项: Flammable/Irritant/Moisture Sensitive/Store under Argon; IRRITANT
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 联合国危险货物编号: 1993; UN3272
• 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; III
• 危险公开号: 10-36/37/38
• 安全公开号: 26-36
• TSCA收录: false; 否
• GHS危险品标识: GHS02; GHS07
• GHS警示词: Warning
• GHS危险声明: H226; H226-H315-H319-H335
• GHS警示性声明: P210-P241-P280-P303+P361+P353-P403+P235-P501A; P261-P305 + P351 + P338
• 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 1993 3/PG 3
• 保存温度: 2-8°C

产品相关信息

• 纯度: 95%; 97%; 98%; 98+%
• 线性分子式: ((CH3)4C2O2)BCH2CH=CH2

详细说明

Sigma Aldrich - 324647

包装
1, 10 g in glass bottle
Application
Reagent used for
• Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions and olefin metathesis1
• Intermolecular radical additions2
• Allylboration of aldehydes catalyzed by chiral spirobiindane diol (SPINOL) based phosphoric acids3
• Cobalt-catalyzed regioselective hydrovinylation of dienes with alkenes4
• Nucleic acid-templated energy transfer leading to a photorelease reaction5
• Stereoselective indium-catalyzed Hosomi-Sakurai reactions6 Reagent used in Preparation of
• Cyclic sulfone hydroxyethylamines as BACE1 inhibitors for reduction of Amyloid β-Peptides7
• Transmetalation of carbene Ru iodide with Ag carboxylates to give C-H-activated Ru carbene complexes as catalysts for Z-selective olefin metathesis8

参考文献

• Reacts with carboxylic acids, in the presence of tri-n-butyltin hydride, to give homoallylic alcohols in good yield: Synthesis, 1573 (2001):
  
• Homoallylic alcohols can also be formed by allylboration of aldehydes; the reaction has been found to be accelerated by Lewis acids, e.g. AlCl₃ or Sc(OTf)₃: J. Am. Chem. Soc., 124, 12414 (2002).