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Tris(hydroxymethyl)phosphine

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Tris(hydroxymethyl)phosphine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.018.587 Edit this at Wikidata
EC Number
  • 220-445-6
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H9O3P/c4-1-7(2-5)3-6/h4-6H,1-3H2Key: JMXMXKRNIYCNRV-UHFFFAOYSA-N
SMILES
  • C(O)P(CO)CO
Properties
Chemical formula C3H9O3P
Molar mass 124.076 g·mol
Appearance white solid
Density 1.16 g/cm
Melting point 51–53 °C (124–127 °F; 324–326 K)
Boiling point decomposes
Solubility in water alcohols, dmf
Hazards
GHS labelling:
Pictograms GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
Signal word Danger
Hazard statements H301, H315, H318, H335
Precautionary statements P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, 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

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:

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.

Reactions

The compound forms complexes with a variety of metals. These complexes display some solubility in water but more so in methanol. 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.

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. ^ 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 Pd4CH3OH". 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.
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