3-Methoxybenzyltriphenylphosphonium chloride Chemical Properties

Melting point:

271-272 °C

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

color 

White to Almost white

Safety Information

HS Code 

2931.90.9051

3-Methoxybenzyltriphenylphosphonium chloride Usage And Synthesis

Uses

(3-Methoxybenzyl)(triphenyl)phosphonium Chloride is an intermediate used in the synthesis of 2-Hydroxychrysene (H905340), which is a hydroxylated metabolite of Chrysene (C428000). Binding activity of 2-Hydroxychrysene to estrogenic receptor induces toxicity.

Synthesis

Example 2: Synthesis of (3-methoxybenzyl)triphenylphosphonium chloride (Compound I, Scheme A, Intermediate) 3-Methoxybenzyl chloride (5 g, 32 mmol) and triphenylphosphonium (9.205 g, 33.93 mmol) were dissolved in acetonitrile (20 mL) and the reaction mixture was stirred under reflux conditions for 12 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The resulting product was dissolved in a minimal amount of chloroform and subsequently precipitated by the addition of ether. The solid formed was collected by filtration to afford the target compound in 98.5% yield. 1H NMR (CDCl3): δ 3.53 (s, 3H, OCH3); 5.44 (d, 2H, J = -16Hz, CH2); 6.60-6.77 (m, 3H, Ar); 7.02 (t, 1H, J = 7.6 Hz); 7.11-7.21 (m, 15H, PPh3) ppm. Mass spectrum (m/z): [M+ -Cl] 383 (16.1%). Elemental analysis results are as expected.

References

[1] Journal of Medicinal Chemistry, 2006, vol. 49, # 22, p. 6607 - 6613
[2] Patent: US2009/93493, 2009, A1. Location in patent: Page/Page column 10
[3] Polymer, 2015, vol. 64, p. 202 - 209
[4] Archiv der Pharmazie, 2001, vol. 334, # 4, p. 125 - 137
[5] Archiv der Pharmazie, 1995, vol. 328, # 7-8, p. 595 - 603

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