82495-75-8

Basic information

• Product Name: 2-(TRIMETHYLSILYL)ETHOXYMETHYLTRIPHENYLPHOSPHONIUM CHLORIDE
• Synonyms: SEM-TRIPHENYLPHOSPHONIUM CHLORIDE;2-(TRIMETHYLSILYL)ETHOXYMETHYLTRIPHENYLPHOSPHONIUM CHLORIDE;-(Trimethylsilyl)ethoxymethyl-triphenylphosphonium chloride;2-(trime-silyl)ethoxymethyl-triphenyl-phosphonium chloride;PHENYL PHOSPHONIUM CHLORIDE;[2-(trimethylsily)ethoxymethyl]triphenylphosphonium.Cl;2-(Trimethylsilyl)ethoxymethyl-triphenylphosphonium chloride,SEM-triphenylphosphonium chloride;Phosphonium, triphenyl[[2-(trimethylsilyl)ethoxy]methyl]-, chloride
• CAS NO: 82495-75-8
• Molecular Formula: C₂₄H₃₀OPSi*Cl
• Molecular Weight: 429.01
• Product Categories: Phosphonium Compounds;Si (Classes of Silicon Compounds);Si-(C)4 Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction;Wittig Reaction
• Mol File: 82495-75-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 145-149 °C(lit.)
• Appearance: /
• Storage Temp.: 2-8°C
• Solubility: Sol H2O and dichloromethane; sparingly soluble in THF.
• BRN: 4632507
• CAS DataBase Reference: 2-(TRIMETHYLSILYL)ETHOXYMETHYLTRIPHENYLPHOSPHONIUM CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(TRIMETHYLSILYL)ETHOXYMETHYLTRIPHENYLPHOSPHONIUM CHLORIDE(82495-75-8)
• EPA Substance Registry System: 2-(TRIMETHYLSILYL)ETHOXYMETHYLTRIPHENYLPHOSPHONIUM CHLORIDE(82495-75-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 3
• Hazardous Substances Data: 82495-75-8(Hazardous Substances Data)

Usage

Physical properties

mp 165–169 °C.

Uses

Different sources of media describe the Uses of 82495-75-8 differently. You can refer to the following data:
1. [2-(Trimethylsilyl)ethoxymethyl]- triphenylphosphonium chloride is a reagent undergoes deprotonation and yield formation permitting the construction of enol ethers from aldehydes and ketones.
2. 2-(Trimethylsilyl)ethoxymethyltriphenylphosphonium Chloride is used in preparation of Benzodecalindiones as antitumor agents.

Preparation

Involves reaction of triphenylphosphine with 2-(trimethylsilyl)ethoxymethyl chloride in benzene at gentle reflux for 18 h. Upon cooling, the resulting phosphonium salt can be recovered by filtration and purified by triturating with diethyl ether in 94% yield.

Purification Methods

Wash the solid with AcOH and recrystallise it from CH2Cl2/EtOAc. Dry it in a vacuum desiccator. Hygroscopic. 1H NMR (CDCl3) : -0.2 (s, Me3Si), 0.8 (t, 8Hz, CH2Si), 3.83 (t, 8Hz, OCH2), 5.77 (d, JPH 4Hz, P+-CH2O) and 7.70 (m, aromatic H). [Sch.nauer & Zbiral Justus Liebigs Ann Chem 1039 1983.]

InChI:InChI=1/C24H30OPSi.ClH/c1-27(2,3)20-19-25-21-26(22-13-7-4-8-14-22,23-15-9-5-10-16-23)24-17-11-6-12-18-24;/h4-18H,19-21H2,1-3H3;1H/q+1;/p-1

Upstream product

• 76513-69-4 (2-trimethylethylsilylethoxy)methyl chloride 
• 603-35-0 triphenylphosphine 
• 2916-68-9 2-(Trimethylsilyl)ethanol 

Downstream Products

• 82495-79-2 (2S)-(Z,Z)-N,N-benzyl-2-<6-(2'-trimethylsilyl)ethoxy-4,5-dimethyl-1-phenyl>hexa-3,5-dienyl-p-toluenesulfonamide 
• 82495-78-1 (2S)-(Z,E)-N,N-benzyl-2-<6-(2'-trimethylsilyl)ethoxy-4,5-dimethyl-1-phenyl>hexa-3,5-dienyl-p-toluenesulfonamide 
• 82535-50-0 (E,Z)-N,N-benzyl-2-<6-(2'-trimethylsilyl)ethoxy-4,5-dimethyl-1-phenyl>hexa-3,5-dienyl-p-toluenesulfonamide 
• 82535-51-1 (E,E)-N,N-benzyl-2-<6-(2'-trimethylsilyl)ethoxy-4,5-dimethyl-1-phenyl>hexa-3,5-dienyl-p-toluenesulfonamide 
• 86400-66-0 triphenyl(trimethylsilylethoxymethylene)phosphorane 
• 86400-67-1 Trimethyl-[2-((E)-styryloxy)-ethyl]-silane 
• 784181-19-7 5-(4-chloro-phenyl)-1-(2-chloro-phenyl)-4-[2-(2-trimethylsilanyl-ethoxy)-vinyl]-1H-pyrazole-3-carboxylic acid ethyl ester 

Relevant articles and documents

Intramolecular Diels-Alder Cycloaddition Approach toward the cis-Fused Δ5,6-Hexahydroisoindol-1-one Core of Cytochalasins

Synthesis of the cis-fused Δ5,6-hexahydroisoindol-1-one core of cytochalasins B2-B5, K, Z8, Z9, Z12-Z15, and Z17 has been established starting from an intramolecular D