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Propargyltriphenylphosphonium bromide can be used in the alcylation of amines. It is a commonly used as a Wittig reagent.
M.H. Wahdan; A.A. Hermas; M.S. Morad. Corrosion inhibition of carbon-steels by propargyltriphenylphosphonium bromide in H2SO4 solution. Materials Chemistry and Physics. 2002, 76(2), 111-118.
Yeong-Soon Gal. A Facile Synthetic Method of Poly(Propargyltriphenylphosphonium-Tetraphenylborate) Via Ion Exchange Reaction of Poly(Propargyltriphenylphosphonium Bromide) Using Tetraphenylboron Sodium. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry. 1995, 321031-1038.
Precursor of enynes by the Wittig reaction: Liebigs Ann. Chem., 682, 62 (1965); J. Org. Chem., 42, 200 (1977); see Appendix 1.
Readily undergoes additions with nucleophiles, e.g. alcohols or amines, to give 2-alkoxy or 2-alkylamino propenyl phosphonium salts. In these reactions, the reactive species is the allenic isomer, propadienyl triphenylphosphonium bromide: J. Org. Chem., 42, 200 (1977). By using a chiral alcohol, the subsequent base-promoted Wittig reaction with carbonyl compounds yields amino or alkoxy dienes which undergo face-selective Diels-Alder additions to dienophiles: J. Chem. Soc., Chem. Commun., 1785 (1995):
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant