Tris(dimethylamino)phosphine is an

organophosphorus compound Organophosphorus compounds are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective in ...

with the formula P(NMe₂)₃ (Me =

methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many ...

). It is a colorless oil at room temperature, and is one of the most common

aminophosphine In organophosphorus chemistry, an aminophosphine is a compound with the formula R3−nP(NR2)n where R = H or an organic substituent, and n = 0, 1, 2. At one extreme, the parent H2PNH2 is lightly studied and fragile, but at the other extreme tris(di ...

s. 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 Triisopropylphosphine is the tertiary phosphine with the formula P( CH(CH3)2)3. Commonly used as a ligand in organometallic chemistry, it is often abbreviated to Pi-Pr3 or PiPr3. This ligand is one of the most basic alkyl phosphines with a l ...

. 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 Dibenzyl sulfide is a symmetrical thioether. It contains two C6H5CH2- (benzyl) groups linked by a sulfide bridge. It is a colorless or white solid that is soluble in nonpolar solvents. Crystallography The crystal structure of the solid is of the ...

:{{cite journal, title= Sulfide Synthesis: Benzyl Sulfide, first1=David N. , last1=Harpp, first2= Roger A., last2=Smith , journal=Org. Synth., year=1978, volume=58, page=138, doi= 10.15227/orgsyn.058.0138 :PhCH₂SSCH₂Ph + P(NMe₂)₃ → S=P(NMe₂)₃ + PhCH₂SCH₂Ph (Ph = phenyl)

References

Phosphines