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2-(TRIMETHYLSILYL)ETHOXYMETHYLTRIPHENYLPHOSPHONIUM CHLORIDE

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2-(TRIMETHYLSILYL)ETHOXYMETHYLTRIPHENYLPHOSPHONIUM CHLORIDE 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
  • triphenyl(2-trimethylsilylethoxymethyl)phosphanium:chloride
CAS:
82495-75-8
MF:
C24H30ClOPSi
MW:
429.01
Product Categories:
  • Wittig Reaction
  • Phosphonium Compounds
  • Si (Classes of Silicon Compounds)
  • Si-(C)4 Compounds
  • Silicon Compounds (for Synthesis)
  • Synthetic Organic Chemistry
  • Wittig & Horner-Emmons Reaction
Mol File:
82495-75-8.mol
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2-(TRIMETHYLSILYL)ETHOXYMETHYLTRIPHENYLPHOSPHONIUM CHLORIDE Chemical Properties

Melting point:
145-149 °C(lit.)
storage temp. 
Sealed in dry,2-8°C
solubility 
Sol H2O and dichloromethane; sparingly soluble in THF.
form 
powder to crystal
color 
White to Almost white
BRN 
4632507
CAS DataBase Reference
82495-75-8(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
3
HS Code 
2931.90.6000

MSDS

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2-(TRIMETHYLSILYL)ETHOXYMETHYLTRIPHENYLPHOSPHONIUM CHLORIDE Usage And Synthesis

Physical properties

mp 165–169 °C.

Uses

2-(Trimethylsilyl)ethoxymethyltriphenylphosphonium Chloride is used in preparation of Benzodecalindiones as antitumor agents.

Uses

[2-(Trimethylsilyl)ethoxymethyl]- triphenylphosphonium chloride is a reagent undergoes deprotonation and yield formation permitting the construction of enol ethers from aldehydes and ketones.

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.]

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