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Tris(hydroxymethyl)phosphine

Tris(hydroxymethyl)phosphine is the organophosphorus compound with the formula P(CH2OH)3. It is a white solid. The compound is multifunctional, consisting of three alcohol functional groups and a tertiary phosphine. It is prepared by treating tetrakis(hydroxymethyl)phosphonium chloride with strong base:[2][3]

[P(CH2OH)4]Cl + NaOH → P(CH2OH)3 + H2O + H2C=O + NaCl

The compound can be prepared on a large scale using triethylamine as base and as solvent.[4]

Reactions

The compound forms complexes with a variety of metals. These complexes display some solubility in water but more so in methanol.[4]The compound decomposes violently to phosphine and formaldehyde upon attempted distillation. In air, it oxidizes to the oxide.

Upon heating with hexamethylenetetramine, it converts to triazaphosphaadamantane.[5]

References

  1. ^ "Tris(hydroxymethyl)phosphine". pubchem.ncbi.nlm.nih.gov.
  2. ^ Ferguson, Marcelle L.; O’Leary, Daniel J.; Grubbs, Robert H. (2003). "Ring-Closing Metathesis Synthesis of N-BOC-3-Pyrroline". Organic Syntheses. 80: 85. doi:10.15227/orgsyn.080.0085{{cite journal}}: CS1 maint: multiple names: authors list (link).
  3. ^ M. Caporali, L. Gonsalvi, F. Zanobini, M. Peruzzini (2010). "Functional Ligands and Complexes". Inorganic Syntheses. Vol. 35. pp. 92–108. doi:10.1002/9780470651568.ch5. ISBN 978-0-471-68255-4.{{cite book}}: CS1 maint: multiple names: authors list (link)
  4. ^ a b Ellis, James W.; Harrison, Karl N.; Hoye, Peter A. T.; Orpen, A. Guy; Pringle, Paul G.; Smith, Martin B. (1992). "Water-Soluble Tris(hydroxymethyl)phosphine Complexes with Nickel, Palladium, and Platinum. Crystal Structure of Pd[P(CH2OH)3]4.CH3OH". Inorganic Chemistry. 31 (14): 3026–3033. doi:10.1021/ic00040a009.
  5. ^ Daigle, D. J.; Pepperman, A. B.; Vail, Sidney L. (1974). "Synthesis of a Monophosphorus Analog of Hexamethylenetetramine". Journal of Heterocyclic Chemistry. 11 (3): 407–408. doi:10.1002/jhet.5570110326.