(4-carboxybutyl)triphenylphosphanium bromide

• ChemBase编号: 74853
• 分子式: C23H24BrO2P
• 平均质量: 443.313221
• 单一同位素质量: 442.06972864
• SMILES: [P+](c1ccccc1)(c1ccccc1)(c1ccccc1)CCCCC(=O)O.[Br-]
• Canonical SMILES: OC(=O)CCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• InChI: InChI=1S/C23H23O2P.BrH/c24-23(25)18-10-11-19-26(20-12-4-1-5-13-20,21-14-6-2-7-15-21)22-16-8-3-9-17-22;/h1-9,12-17H,10-11,18-19H2;1H
• InChIKey: MLOSJPZSZWUDSK-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: (4-carboxybutyl)triphenylphosphanium bromide
• IUPAC传统名: (4-carboxybutyl)triphenylphosphanium bromide
• 别名: (4-羧丁基)三苯基溴化磷鎓; (4-羧丁基)三苯基溴化膦; (4-Carboxybutyl)triphenylphosphonium bromide; (4-Carboxybutyl)triphenyl-phosphonium Bromide; Triphenyl(4-carboxybutyl)phosphonium Bromide; 5-(Triphenylphosphonio)pentanoic acid bromide; Carboxybutyltriphenylphosphonium bromide; NSC 147756; (4-Carboxybutyl)triphenylphosphonium bromide

登记号

• CAS号: 17814-85-6
• EC号: 241-782-5
• MDL号: MFCD00011906
• Beilstein号: 3586477
• PubChem SID: 24849711; 162039771
• PubChem CID: 161236

理论计算性质

• Acid pKa: 3.8977032
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 3.4681077
• LogD (pH = 7.4): 1.8612405
• Log P: 5.076017
• 摩尔折射率: 107.3612 cm^3
• 极化性: 42.217678 Å^3
• 极化表面积: 37.3 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO; Methanol
• 外观: White Solid
• 熔点: 198-200°C; 204-207 °C(lit.); 205-209°C
• 闪点: 195°C(383°F)

安全信息

• 保存条件: Refrigerator
• 保存注意事项: Hygroscopic; Irritant/Hygroscopic
• 欧盟危险性物质标志: X; 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 22; 36/37/38
• 安全公开号: 26-36; 36
• TSCA收录: 否
• GHS危险品标识: GHS06; GHS07
• GHS警示词: Warning
• GHS危险声明: H301; H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P264-P270-P301+P310-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: 98%
• 线性分子式: (C6H5)3P(Br)(CH2)4COOH

详细说明

Sigma Aldrich - 157945

包装
10, 50, 250 g in poly bottle
Application

• Used as a platform for delivery of pro-apoptotic peptides into the mitochondria of tumor cells1Reactant for preparation of:
• Ring skeletons via ring closing metathesis and double bond migration ring closing metathesis reactions2
• Methyl alkenyl quinolones as antimycobacterial agents3
• Prostaglandins and their drug analogs via Gold-catalyzed Meyer-Schuster rearrangement4
• Diphenylmethylpiperazines as N-type calcium channel blockers as potential therapeutic agents5
• Folate receptor-specific glycinamide ribonucleotide formyltransferase (GARFTase) inhibitors with antitumor activity6
• Cycloalkylidene alkanols with antileishmanial activity, via Wittig reaction7

参考文献

• Use of LiHMDS as base in the Wittig reaction with aromatic aldehydes gives a much higher proportion of the trans-alkene than alternative bases such as dimsyl sodium or KO-t-Bu: Tetrahedron Lett., 22, 4185 (1981). See Appendix 1.