triphenyl(prop-2-en-1-yl)phosphanium bromide

• ChemBase编号: 108935
• 分子式: C21H20BrP
• 平均质量: 383.261261
• 单一同位素质量: 382.04859927
• SMILES: [Br-].C=CC[P+](c1ccccc1)(c1ccccc1)c1ccccc1
• Canonical SMILES: C=CC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• InChI: InChI=1S/C21H20P.BrH/c1-2-18-22(19-12-6-3-7-13-19,20-14-8-4-9-15-20)21-16-10-5-11-17-21;/h2-17H,1,18H2;1H/q+1;/p-1
• InChIKey: FWYKRJUVEOBFGH-UHFFFAOYSA-M

名称和登记号

名称

• IUPAC标准名: triphenyl(prop-2-en-1-yl)phosphanium bromide
• IUPAC传统名: triphenyl(prop-2-en-1-yl)phosphanium bromide
• 别名: 烯丙基三苯基溴化膦; 烯丙基三苯基溴化鏻; ALLYLTRIPHENYLPHOSPHONIUM BROMIDE; 2-Propenyltriphenylphosphonium bromide; NSC 110609; NSC 59815; Allyltriphenylphosphonium bromide

登记号

• CAS号: 1560-54-9
• EC号: 216-332-6
• MDL号: MFCD00011808
• Beilstein号: 3579053
• PubChem SID: 162094639; 24890798
• PubChem CID: 197740

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 5.3590407
• LogD (pH = 7.4): 5.3590407
• Log P: 5.3590407
• 摩尔折射率: 96.3839 cm^3
• 极化性: 37.899105 Å^3
• 极化表面积: 0.0 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: false

分子性质

理化性质

• 熔点: 222-225 °C(lit.); 222-225°C

安全信息

• 保存注意事项: Hygroscopic
• RTECS编号: TA1843000
• 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; R:36/37/38
• 安全公开号: 26-37; 26-37/39; S:20-25-26-37/39
• TSCA收录: 否
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: 97%; 98%; 99%
• 线性分子式: H2C=CHCH2P(C6H5)3Br

详细说明

MP Biomedicals - 05209285

MP Biomedicals Rare Chemical collection

Sigma Aldrich - A36603

包装
100 g in poly bottle
Application
Reactant for:
• Preparation of a diol and carbamate chemistry library for common functional groups1
• Regioselective synthesis of alkenes via semihydrogenation and semihydrogenation-oxidation of dienes2
• Alkene addition of frustrated Lewis pairs3
• Olefination of N-sulfonyl imines for stereoselective synthesis of vinyl arenes4
• Wittig olefination of aldehydes for preparation of conjugated dienes5
• Tandem Michael addition / ylide olefination reactions for the synthesis of highly functionalized cyclohexadienes6

参考文献

• Wittig reaction (see Appendix 1) with aldehydes, using K₂CO₃ in toluene, gives dienes: Synth. Commun., 22, 1421 (1992). The derived phosphorane also reacts with ?-chloroacrylates to give conjugated phosphoranes, convertible to trienes: Tetrahedron Lett., 1359 (1975):
  
• Michael addition of the phosphorane to ɑ?-unsaturated ketones, followed by intramolecular Wittig reaction, gives cyclohexa-1,3-dienes: Tetrahedron Lett., 4425 (1973). Further lithiation of the phosphorane in the presence of TMEDA, followed by reaction of the ylide anion with an aldehyde, provides a route to (E,E)-?-hydroxy-1,3-dienes: Tetrahedron Lett., 32, 4353 (1991).