Tris(dimethylamino)phosphine is an
organophosphorus compound
Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbo ...
with the formula P(NMe
2)
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 (whereas normal methane has the formula ). In formulas, the group is often abbreviated as ...
). It is a colorless oil at room temperature, and is one of the most common
aminophosphine In organophosphorus chemistry, aminophosphines are compounds with the formula R3−nP(NR2)n where R is a hydrogen or organic substituent, and n = 0, 1, or 2. At one extreme, the parents H2PNH2 and are lightly studied and fragile. At the other extre ...
s. Its structure has been determined by
X-ray crystallography
X-ray crystallography is the experimental science of determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to Diffraction, diffract in specific directions. By measuring th ...
.
Tris(dimethylamino)phosphine acts as a base. It reacts with oxygen to give
hexamethylphosphoramide
Hexamethylphosphoramide, often abbreviated HMPA, is a phosphoramide (an amide of phosphoric acid) with the formula This colorless liquid is used as a solvent in organic synthesis.
Structure and reactivity
HMPA is the oxide of tris(dimethyla ...
, O=P(NMe
2)
3, and with sulfur to give the corresponding compound hexamethylthiophosphoramide, S=P(NMe
2)
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:
[{{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]
:PhCH
2SSCH
2Ph + P(NMe
2)
3 → S=P(NMe
2)
3 + PhCH
2SCH
2Ph (Ph =
phenyl
In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula , and is often represented by the symbol Ph (archaically φ) or Ø. The phenyl group is closely related to benzene and can be viewed as a benzene ...
)
References
Phosphines