Tris(hydroxymethyl)phosphine

Tris(hydroxymethyl)phosphine
Identifiers
CAS Number	2767-80-8 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL279546;
ChemSpider	68500;
ECHA InfoCard	100.018.587
EC Number	220-445-6;
PubChem CID	76001;
UNII	Y6TG7WF7OQ;
CompTox Dashboard (EPA)	DTXSID0062634;
	InChI InChI=1S/C3H9O3P/c4-1-7(2-5)3-6/h4-6H,1-3H2 Key: JMXMXKRNIYCNRV-UHFFFAOYSA-N;
	SMILES C(O)P(CO)CO;
Properties
Chemical formula	C3H9O3P
Molar mass	124.076 g·mol−1
Appearance	white solid
Density	1.16 g/cm3
Melting point	51–53 °C (124–127 °F; 324–326 K)
Boiling point	decomposes
Solubility in water	alcohols, dmf
Hazards
	GHS labelling:
Pictograms
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 [77 °F], 100 kPa). Infobox references

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

^ "Tris(hydroxymethyl)phosphine". pubchem.ncbi.nlm.nih.gov.
^ 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).
^ 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)
^ ^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.
^ 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.

[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)

[Pringle-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 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.

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