(cyanomethyl)triphenylphosphanium chloride

• ChemBase编号: 74857
• 分子式: C20H17ClNP
• 平均质量: 337.782441
• 单一同位素质量: 337.07871386
• SMILES: [P+](c1ccccc1)(c1ccccc1)(c1ccccc1)CC#N.[Cl-]
• Canonical SMILES: N#CC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Cl-]
• InChI: InChI=1S/C20H17NP.ClH/c21-16-17-22(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20;/h1-15H,17H2;1H/q+1;/p-1
• InChIKey: ARPLQAMUUDIHIT-UHFFFAOYSA-M

名称和登记号

名称

• IUPAC标准名: (cyanomethyl)triphenylphosphanium chloride
• IUPAC传统名: (cyanomethyl)triphenylphosphanium chloride
• 别名: (氰甲基)三苯基氯化膦; (氰甲基)三苯基氯化磷鎓; NSC 92174; (Cyanomethyl)triphenylphosphonium chloride; (Cyanomethyl)triphenylphosphonium chloride

登记号

• CAS号: 4336-70-3
• EC号: 224-383-0
• MDL号: MFCD00031672
• Beilstein号: 6222047
• PubChem SID: 24870234; 162039775
• PubChem CID: 197040

理论计算性质

• Acid pKa: 7.5955844
• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 3.952703
• LogD (pH = 7.4): 3.7425656
• Log P: 3.9561672
• 摩尔折射率: 92.3835 cm^3
• 极化性: 36.063854 Å^3
• 极化表面积: 23.79 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: 275 °C (dec.)(lit.); ca 270°C dec.

安全信息

• 保存注意事项: Hygroscopic; Toxic
• RTECS编号: TA2075000
• 欧盟危险性物质标志: X; 有害性(Harmful) (Xn)
• 联合国危险货物编号: UN3439
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): III
• 危险公开号: 20/21/22-36/37/38
• 安全公开号: 26-36/37; 26-37/39
• TSCA收录: 否
• GHS危险品标识: GHS06; GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H312-H315-H319-H332-H335; H331-H302-H312-H315-H319-H335
• GHS警示性声明: P261-P280-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: 95+%; 98%; 98+%
• 线性分子式: NCCH2P(C6H5)3Cl

详细说明

Sigma Aldrich - 464937

包装
25 g in glass bottle
Application
Reactant involved in:
• Condenation reactions1,2
• Wittig reactions3,4,5
• Synthesis of phosphonium-iodonium ylides6
• Preparation of α,β-unsaturated esters, amides, and nitriles7

参考文献

• Forms a moderately stable crystalline ylide which reacts with aldehydes to give ɑ?-unsaturated nitriles, predominantly as their (Z)-isomers: Chem. Ber., 94, 578 (1961); J. Chem. Soc., 1266 (1961); Appendix 1.
• Further deprotonation of the phosphorane with sodium bis(trimethylsilyl)amide followed by C-alkylation generates a homologated phosphorane: Angew. Chem. Int. Ed., 26, 79 (1987).
• Reaction of the ylide with carboxylic acids in the presence of EDCI (1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, A10807) and DMAP, followed by ozonolysis of the resulting acylphosphoranes, provides a novel route to the homologous ɑ-keto esters: J. Org. Chem., 59, 4364 (1994):