Methyltriphenylphosphonium bromide
Appearance
![]() | |
Names | |
---|---|
Preferred IUPAC name
Methyltri(phenyl)phosphanium bromide | |
Identifiers | |
3D model (JSmol)
|
|
ChEMBL | |
ChemSpider | |
EC Number |
|
PubChem CID
|
|
UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
Properties | |
C19H18BrP | |
Molar mass | 357.231 g·mol−1 |
Appearance | white solid |
Hazards | |
GHS labelling: | |
![]() ![]() ![]() | |
Danger | |
H300, H301, H302, H312, H315, H319, H332, H411 | |
P261, P264, P270, P271, P273, P280, P301+P310, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P391, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
Methyltriphenylphosphonium bromide is the organophosphorus compound with the formula [(C6H5)3PCH3]Br. It is the bromide salt of a phosphonium cation. It is a white salt that is soluble in polar organic solvents.
Synthesis and reactions
[edit]Methyltriphenylphosphonium bromide is produced by treating triphenylphosphine with methyl bromide:[1]
- Ph3P + CH3Br → Ph3PCH3Br
Methyltriphenylphosphonium bromide is the principal precursor to methylenetriphenylphosphorane, a useful methylenating reagent. This conversion is achieved by treating methyltriphenylphosphonium bromide with strong base.[2]
- Ph3PCH3Br + BuLi → Ph3PCH2 + LiBr + BuH
References
[edit]- ^ Wittig, Georg; Schoellkopf, U. (1960). "Methylenecyclohexane". Organic Syntheses. 40: 66. doi:10.15227/orgsyn.040.0066.
- ^ Fitjer, Lutz; Quabeck, Ulrike (1985). "The Wittig Reaction Using Potassium-tert-butoxide High Yield Methylenations of Sterically Hindered Ketones". Synthetic Communications. 15 (10): 855–864. doi:10.1080/00397918508063883.