Tetramethylphosphonium bromide
Tetramethylphosphonium bromide is an organophosphorus compound with the formula (CH3)4PBr. It is a white, water-soluble solid, the salt of the cation tetramethylphosphonium and the bromide anion. It is prepared by treating trimethylphosphine with methyl bromide.
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3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.152.249 |
PubChem CID |
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| Properties | |
| C4H12BrP | |
| Molar mass | 171.018 g·mol−1 |
| Appearance | white solid |
| Hazards | |
| GHS pictograms |  |
| GHS Signal word | Warning |
GHS hazard statements |
H315, H319, H335 |
| P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Reactions
2)Cu)2.png)
Structure of Cu2[(Me2P(CH2)2]2.
Deprotonation gives methylenetrimethylphosphine ylide, which can sustain a second deprotonation:[1]
- (CH3)4PBr + BuLi → CH3)3P=CH2 + LiBr + BuH
- CH3)3P=CH2 + BuLi → CH3)2P(CH2)2Li + BuH
The latter is a precursor to many coordination complexes, e.g., the dicuprous complex Cu2[(Me2P(CH2)2]2.[2]
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References
- H. F. Klein (1978). "Trimethylphosphonium Methylide (Trimethyl Methylenephosphorane)". Inorganic Syntheses. XVIII: 138–140. doi:10.1002/9780470132494.ch23.
- Schmidbaur, H. (1983). "Phosphorus Ylides in the Coordination Sphere of Transition Metals: An Inventory". Angewandte Chemie International Edition in English. 22 (12): 907–927. doi:10.1002/anie.198309071.
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