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Tetramethylphosphonium bromide

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A white, water-soluble organophosphorus compound
Tetramethylphosphonium bromide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.152.249 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H12P.BrH/c1-5(2,3)4;/h1-4H3;1H/q+1;/p-1Key: ZTXFOCMYRCGSMU-UHFFFAOYSA-M
SMILES
  • C(C)(C)C.
Properties
Chemical formula C4H12BrP
Molar mass 171.018 g·mol
Appearance white solid
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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.

Reactions

Structure of Cu22.

Deprotonation gives methylenetrimethylphosphine ylide, which can sustain a second deprotonation:

(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 Cu22.

References

  1. H. F. Klein (1978). "Trimethylphosphonium Methylide (Trimethyl Methylenephosphorane)". Inorganic Syntheses. Vol. XVIII. pp. 138–140. doi:10.1002/9780470132494.ch23. ISBN 978-0-471-03393-6.
  2. 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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