ethenyltriphenylphosphanium bromide

• ChemBase编号: 146955
• 分子式: C20H18BrP
• 平均质量: 369.234681
• 单一同位素质量: 368.03294921
• SMILES: C=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• Canonical SMILES: C=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• InChI: InChI=1S/C20H18P.BrH/c1-2-21(18-12-6-3-7-13-18,19-14-8-4-9-15-19)20-16-10-5-11-17-20;/h2-17H,1H2;1H/q+1;/p-1
• InChIKey: VRAYVWUMBAJVGH-UHFFFAOYSA-M

名称和登记号

名称

• IUPAC标准名: ethenyltriphenylphosphanium bromide
• IUPAC传统名: ethenyltriphenylphosphanium bromide
• 别名: Schweizer 试剂; 乙烯基三苯基溴化膦; 溴化乙烯基三苯基膦; Ethenyltriphenylphosphonium bromide; NSC 84065; Schweizer’s Reagent; Vinyltriphenylphosphonium bromide; Triphenylvinylphosphonium bromide; Triphenyl(vinyl)phosphonium bromide; Schweizer's Reagent; Triphenylvinylphosphonium bromide; Vinyltriphenylphosphonium bromide

登记号

• CAS号: 5044-52-0
• EC号: 225-740-3
• MDL号: MFCD00011807
• Beilstein号: 4168860
• PubChem SID: 24848845; 162241147
• PubChem CID: 2723893

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 4.8482046
• LogD (pH = 7.4): 4.8482046
• Log P: 4.8482046
• 摩尔折射率: 91.1052 cm^3
• 极化性: 36.061058 Å^3
• 极化表面积: 0.0 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: ~180 °C; 176-178 °C(lit.); 182-186°C

安全信息

• 保存注意事项: Light Sensitive & Hygroscopic
• 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: 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
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥95% (AT); 95+%; 97%
• 级别: technical
• 线性分子式: CH2=CHP(Br)(C6H5)3

详细说明

Sigma Aldrich - 150193

Application
合成杂环化合物的试剂。
Reactant involved in:
• Asymmetric conjugate addition and intramolecular cyclization1
• Condensation with benzoxazinediones2
• Intramolecular dehydrobromination3
• Schweizer reaction4
• Cycloaddition with nitro ketone Baylis-Hillman adducts5
包装
25 g in glass bottle

Sigma Aldrich - 93155

Other Notes
制备烯丙胺的试剂6
Application
Reactant involved in:
• Asymmetric conjugate addition and intramolecular cyclization1
• Condensation with benzoxazinediones2
• Intramolecular dehydrobromination3
• Schweizer reaction4
• Cycloaddition with nitro ketone Baylis-Hillman adducts5

参考文献

• Conjugate additions of nucleophiles to the double bond give ?-substituted ethyl triphenylphosphonium salts which can be further reacted by Wittig olefination. Sequential reaction with phthalimide and an aldehyde leads, after hydrazinolysis of the resulting N-allylphthalimide, to 3-substituted allylamines: J. Org. Chem., 46, 3119 (1981). N-Alkyl allylamines can also be prepared from alkylamines: Tetrahedron Lett., 24, 3043 (1983):
  
• A variety of heterocyclic systems can be synthesized by conjugate addition and subsequent Wittig condensation: J. Am. Chem. Soc., 86, 2744, 2963 (1964); J. Org. Chem., 33, 2416 (1968). Use of carbon nucleophiles permits synthesis of carbocyclic systems: J. Org. Chem., 30, 2082 (1965).
• Conjugate addition of organocuprates leads to a new phosphonium salt which can be used in the Wittig olefination. With alkenyl cuprates this provides a stereoselective route to (Z,Z)-1,4-pentadienes: Tetrahedron Lett., 26, 1799 (1985). Sequential reactions, catalyzed by CuBr - Ag₂CO₃ or CuBr - H₂O, with Grignard reagents and Wittig olefination with an aldehyde, have also been reported: J. Org. Chem., 61,9659 (1996):