Tris(cyanoethyl)phosphine is the

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(CH₂CH₂CN)₃. It is white solid that is air stable, which is unusual for a trialkylphosphine. It is prepared by the

hydrophosphination Hydrophosphination is the insertion of a double bond into a phosphorus-hydrogen bond. Often the hydrophosphination makes phosphorus-carbon bonds by addition of P-H bonds to carbon-carbon multiple bonds, but the reaction is probably most useful in ...

acrylonitrile Acrylonitrile is an organic compound with the formula and the structure . It is a colorless, volatile liquid. It has a pungent odor of garlic or onions. Its molecular structure consists of a vinyl group () linked to a nitrile (). It is an im ...

with

phosphine Phosphine (IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula , classed as a pnictogen hydride. Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like rotting ...

. The compound has been the subject of much research. For example, it is an effective reagent for the desulfurization of organic

disulfide In chemistry, a disulfide (or disulphide in British English) is a compound containing a functional group or the anion. The linkage is also called an SS-bond or sometimes a disulfide bridge and usually derived from two thiol groups. In inorg ...

s.{{cite journal, doi=10.1021/jo00008a014, title=Selective Reduction of Disulfides by Tris(2-carboxyethyl)phosphine, journal=The Journal of Organic Chemistry, volume=56, issue=8, pages=2648–2650, year=1991, last1=Burns, first1=John A., last2=Butler, first2=James C., last3=Moran, first3=John, last4=Whitesides, first4=George M.

References

Tertiary phosphines Nitriles