Tris(dimethylamino)phosphine

Tris(dimethylamino)phosphine
Names
Preferred IUPAC name
N,N,N′,N′,N′′,N′′-Hexamethylphosphanetriamine
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
  • 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:
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).
Infobox references

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.

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. Its steric and electronic properties are similar to those of triisopropylphosphine.

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:

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