Chemical Properties
white powder
Uses
Methyltriphenylphosphonium bromide is used for methylenation through the Wittig reaction. It is utilized in the synthesis of an enyne and 9-isopropenyl -phenanthrene by using sodium amide as reagent. It is a lipophilic molecule and used to deliver molecules to specific cell components. Further, it acts as an antineoplastic agent.
Uses
Methyltriphenylphosphonium Bromide is a lipophilic molecule with a cation allowing for it to be used to deliver molecules to specific cell components. Also considered an antineoplastic agent.
General Description
Methyltriphenylphosphoniumbromide is an organophosphorus compound, with potential use as a precursor and a solvent in organic synthesis.
Mettler-Toledo calibration substance ME 30130598, methyltriphenylphosphoniumbromide is ideal for use in the regular calibration of Mettler-Toledo melting point instrument. Its value is a mean of 6 to 12 iterations with a Mettler-Toledo MP70 Excellence instrument that is calibrated against primary standards. The melting point is validated by Capillary method according to European Pharmacopeia (2.2.14.)
reaction suitability
reaction type: C-C Bond Formation
Synthesis
Triphenylphosphine (10.0 g, 38 mmol) and methanol (20 mL) were used as raw materials, and 48% hydrobromic acid was added sequentially in a 100 mL round bottom flask. The reaction mixture was heated and refluxed at 110 °C for 8 h. The reaction process was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was cooled to room temperature, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure at 60 °C to give 13.3 g of white crystalline solid methyltriphenylphosphonium bromide in 99.2% yield.
Purification Methods
If the solid is sticky, wash it with *C6H6 and dry it in a vacuum over P2O5. [Marvel & Gall J Org Chem 24 1494 1959, Chem Ber 87 1318 1954, Milas & Priesing J Am Chem Soc 79 6295 1957, Wittig & Sch.llkopf Org Synth 40 66 1960.] The iodide, on recrystallisation from H2O, has m 187.5-188.5o [Mann et al. J Chem Soc 1130 1953, Wittig & Geissler Justus Liebigs Ann Chem 580 44 1953]. [Beilstein 16 IV 981.]
References
[1] Patent: CN107840792, 2018, A. Location in patent: Paragraph 0041; 0042
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 48, # 1-4, p. 279 - 280
[3] Synlett, 2014, vol. 25, # 1, p. 148 - 152
