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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.
Precursor of Wittig ylide for methylenation of carbonyl compounds (see Appendix 1). See, e.g.: Org. Synth. Coll., 5, 751 (1973). A simplified procedure using K2CO3 in triglyme has been reported: Synth. Commun., 22, 513 (1992).
Where the ylide is insufficiently reactive, a further proton can be removed by s-BuLi or t-BuLi, and the resulting lithio ylide reacted with hindered ketones such as fenchone: J. Am. Chem. Soc., 104, 4724 (1982). Reaction of the lithio ylide with an epoxide generates a new ylide, with which Wittig olefination of aldehydes gives trans-homoallylic alcohols (same ref.):
Aissaoui, T.; AlNashef, I. M.; Hayyan, M.; Hashim, M. A. Neoteric FT-IR investigation on the functional groups of phosphonium-based deep eutectic solvents. Spectrochim. Acta Mol. Biomol. Spectrosc. 2015, 149, 588-591.
Chou, Y. H.; Takasugi, S.; Goseki, R.; Ishizone, T.; Chen, W. C. Nonvolatile organic field-effect transistor memory devices using polymer electrets with different thiophene chain lengths. Polym. Chem. 2014, 5 (3), 1063-1071.
Hazard Statements: H301-H335-H500
Toxic if swallowed. May cause respiratory irritation. May form combustible dust concentrations in air
Precautionary Statements: P261-P264b-P270-P271-P301+P310-P304+P340-P312-P330-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth. Dispose of contents/ container to an approved waste disposal plant