Tris(dimethylamino)phosphine

Tris(dimethylamino)phosphine is the organophosphorus compound with the formula P(NMe2)3 (Me = methyl). It is a colorless oil that is one of the most common aminophosphines. Its structure has been determined by X-ray crystallography.[1]

Tris(dimethylamino)phosphine
Names
Other names
Hexamethylphosphorous triamide; HMPT
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.015.032
EC Number
  • 216-534-4
906778
RTECS number
  • TH3390000
UNII
Properties
C6H18N3P
Molar mass 163.205 g·mol−1
Appearance colorless liquid
Density 1.08 g/cm3
Boiling point 49 °C (120 °F; 322 K) 11 torr
Hazards
GHS pictograms
GHS Signal word Warning
GHS hazard statements
H226
P210, P233, P240, P241, P242, P243, P280, P303+361+353, P370+378, P403+235, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

It is basic, reacting with oxygen and sulfur to give the hexamethylphosphoramide (OP(NMe2)3) and the phosphine sulfide SP(NMe2)3. It is also a ligand, forming complexes with a variety of metal centers.[2] Its steric and electronic properties are similar to those of triisopropylphosphine.[3]

Being highly basic, tris(dimethylamino)phosphine is effective as desulfurization agent, e.g. the conversion of dibenzyldisulfide into the dibenzylsulfide:[4]

RSSR + P(NMe2)3 → S=P(NMe2)3 + RSR

References

  1. Mitzel, Norbert W.; Smart, Bruce A.; Dreihäupl, Karl-Heinz; Rankin, David W. H.; Schmidbaur, Hubert (1996). "Low Symmetry in P(NR2)3Skeletons and Related Fragments: An Inherent Phenomenon". Journal of the American Chemical Society. 118 (50): 12673–12682. doi:10.1021/ja9621861.
  2. King, R. B. (1963). "Complexes of Trivalent Phosphorus Derivatives. II. Metal Carbonyl Complexes of Tris(dimethylamino)-phosphine". Inorganic Chemistry. 2 (5): 936–944. doi:10.1021/ic50009a014.
  3. Tolman, C. A. (1977). "Steric effects of phosphorus ligands in organometallic chemistry and homogeneous catalysis". Chem. Rev. 77 (3): 313–348. doi:10.1021/cr60307a002.
  4. Harpp, David N.; Smith, Roger A. (1978). "Sulfide Synthesis: Benzyl Sulfide". Org. Synth. 58: 138. doi:10.15227/orgsyn.058.0138.
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