Tris(dimethylamino)phosphine

Tris(dimethylamino)phosphine
Names
	Preferred IUPAC name N,N,N′,N′,N′′,N′′-Hexamethylphosphanetriamine
	Other names Hexamethylphosphorous triamide; HMPT;
Identifiers
CAS Number	1608-26-0;
3D model (JSmol)	Interactive image;
ChemSpider	14616;
ECHA InfoCard	100.015.032
EC Number	216-534-4;
Gmelin Reference	906778
PubChem CID	15355;
RTECS number	TH3395000;
UNII	6072HG2UW4;
CompTox Dashboard (EPA)	DTXSID6061816;
	InChI InChI=1S/C6H18N3P/c1-7(2)10(8(3)4)9(5)6/h1-6H3 Key: XVDBWWRIXBMVJV-UHFFFAOYSA-N;
	SMILES CN(C)P(N(C)C)N(C)C;
Properties
Chemical formula	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:
Pictograms
Signal word	Warning
Hazard statements	H226
Precautionary statements	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.^[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

^ ^a ^b This name is also used to refer to hexamethylphosphoramide
^ 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/ja9621861.12673-12682&rft.date=1996&rft_id=info:doi/10.1021/ja9621861&rft.aulast=Mitzel&rft.aufirst=Norbert W.&rft.au=Smart, Bruce A.&rft.au=Dreihäupl, Karl-Heinz&rft.au=Rankin, David W. H.&rft.au=Schmidbaur, Hubert&rfr_id=info:sid/en.wikipedia.org:Tris(dimethylamino)phosphine" class="Z3988">
^ 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/ic50009a014.936-944&rft.date=1963&rft_id=info:doi/10.1021/ic50009a014&rft.aulast=King&rft.aufirst=R. B.&rfr_id=info:sid/en.wikipedia.org:Tris(dimethylamino)phosphine" class="Z3988">
^ Tolman, C. A. (1977). "Steric effects of phosphorus ligands in organometallic chemistry and homogeneous catalysis". Chem. Rev. 77 (3): 313–348. doi:10.1021/cr60307a002.313-348&rft.date=1977&rft_id=info:doi/10.1021/cr60307a002&rft.aulast=Tolman&rft.aufirst=C. A.&rfr_id=info:sid/en.wikipedia.org:Tris(dimethylamino)phosphine" class="Z3988">
^ Harpp, David N.; Smith, Roger A. (1978). "Sulfide Synthesis: Benzyl Sulfide". Org. Synth. 58: 138. doi:10.15227/orgsyn.058.0138.

[HMPT-1] 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/ja9621861.12673-12682&rft.date=1996&rft_id=info:doi/10.1021/ja9621861&rft.aulast=Mitzel&rft.aufirst=Norbert W.&rft.au=Smart, Bruce A.&rft.au=Dreihäupl, Karl-Heinz&rft.au=Rankin, David W. H.&rft.au=Schmidbaur, Hubert&rfr_id=info:sid/en.wikipedia.org:Tris(dimethylamino)phosphine" class="Z3988">

[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/ic50009a014.936-944&rft.date=1963&rft_id=info:doi/10.1021/ic50009a014&rft.aulast=King&rft.aufirst=R. B.&rfr_id=info:sid/en.wikipedia.org:Tris(dimethylamino)phosphine" class="Z3988">

[Tolman-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/cr60307a002.313-348&rft.date=1977&rft_id=info:doi/10.1021/cr60307a002&rft.aulast=Tolman&rft.aufirst=C. A.&rfr_id=info:sid/en.wikipedia.org:Tris(dimethylamino)phosphine" class="Z3988">

[5] 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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