General description

Tris(2-carboxyethyl)phosphine hydrochloride (TCEP.HCl) is a non-volatile solid. It is a strong reducing agent.1 It can be synthesized by the acid hydrolysis of tris(2-cyanoethyl)phosphine in refluxing aqueous HCl.1 It has various biological applications such as in vitro and in vivo reduction of disulfide bonds in various peptides and proteins. TCEP is a useful chelating agent for various heavy metal ions as Zn(II), Cd(II), Pb(II), and Ni(II).

Application

Tris(2-carboxyethyl)phosphine hydrochloride (TCEP. HCl) can be used:

As a reducing agent for the reduction of sulfoxides, sulfonyl chlorides, N-oxides, and azides. It can also be used in azide-alkyne cycloaddition reaction in the presence of a copper catalyst.
To reduce disulfide bonds in various proteins.
As a reagent for the selective reduction of disulfides in water.
To remove ruthenium-derived metathesis catalysts via aqueous washing of a crude reaction mixture when it is basified.
As a reducing agent for the reduction of various alkyl disulfides such as trans-4,5-dihydroxy-1,2-dithiane.

Water soluble reagent, used for selective reduction of disulfides. More stable than DTT and useful in mass spectrometry applications.