Tris(dimethylamino)phosphine

Tris(dimethylamino)phosphine
Names
Preferred IUPAC name
N,N,N′,N′,N′′,N′′-Hexamethylphosphanetriamine
Other names
  • Hexamethylphosphorous triamide[1]
  • HMPT[1]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.015.032 Edit this at Wikidata
EC Number
  • 216-534-4
906778
RTECS number
  • TH3390000
UNII
  • InChI=1S/C6H18N3P/c1-7(2)10(8(3)4)9(5)6/h1-6H3
    Key: XVDBWWRIXBMVJV-UHFFFAOYSA-N
  • CN(C)P(N(C)C)N(C)C
Properties
C6H18N3P
Molar mass 163.205 g·mol−1
Appearance colorless liquid
Density 0.898 g/cm3
Boiling point 49 °C (120 °F; 322 K) 11 torr
Hazards
GHS labelling:
GHS02: Flammable
Warning
H226
P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tris(dimethylamino)phosphine is an organophosphorus compound with the formula P(NMe2)3 (Me = methyl). It is a colorless oil at room temperature, and is one of the most common aminophosphines. Its structure has been determined by X-ray crystallography.[2]

Tris(dimethylamino)phosphine acts as a base. It reacts with oxygen to give hexamethylphosphoramide, O=P(NMe2)3, and with sulfur to give the corresponding compound hexamethylthiophosphoramide, S=P(NMe2)3. It can also act as a ligand, forming complexes with a variety of metal centers.[3] Its steric and electronic properties are similar to those of triisopropylphosphine.[4]

Because of its affinity for sulfur, tris(dimethylamino)phosphine is also effective as a desulfurization agent, e.g., in the conversion of dibenzyl disulfide into dibenzyl sulfide:[5]

PhCH2SSCH2Ph + P(NMe2)3 → S=P(NMe2)3 + PhCH2SCH2Ph (Ph = phenyl)

References

  1. ^ a b This name is also used to refer to hexamethylphosphoramide
  2. ^ Mitzel, Norbert W.; Smart, Bruce A.; Dreihäupl, Karl-Heinz; Rankin, David W. H.; Schmidbaur, Hubert (1996). "Low Symmetry in P(NR2)3 Skeletons and Related Fragments: An Inherent Phenomenon". Journal of the American Chemical Society. 118 (50): 12673–12682. doi:10.1021/ja9621861.
  3. ^ 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.
  4. ^ 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.
  5. ^ Harpp, David N.; Smith, Roger A. (1978). "Sulfide Synthesis: Benzyl Sulfide". Org. Synth. 58: 138. doi:10.15227/orgsyn.058.0138.