Tris(dimethylamino)phosphine

Names
Preferred IUPAC name

N,N,N′,N′,N′′,N′′-Hexamethylphosphanetriamine

Other names

* Hexamethylphosphorous triamide[1]
* HMPT[1]

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 |

* TH3390000

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

Chemical compound

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

[edit]

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/ja9621861.12673-12682&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">
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.

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[H226]: H226: Flammable liquid and vapour
*[P210]: P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.
*[P233]: P233: Keep container tightly closed.
*[P240]: P240: Ground and bond container and receiving equipment.
*[P241]: P241: Use explosion-proof electrical/ventilating/light/.../equipment.
*[P242]: P242: Use only non-sparking tools.
*[P243]: P243: Take precautionary measures to prevent static discharges.
*[P280]: P280: Wear protective gloves/protective clothing/eye protection/face protection.
*[P303+P361+P353]: P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water [or shower].
*[P370+P378]: P370+P378: In case of fire: Use ... to extinguish.
*[P403+P235]: P403+P235: Store in a well ventilated place. Keep cool.
*[P501]: P501: Dispose of contents/container to ...