Tris(2-carboxyethyl)phosphine hydrochloride (TCEP.HCl) is a non-volatile solid, it is a strong reducing agent.

Synthesis

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

Applications in Analytical Chemistry

Tris(2-carboxyethyl)phosphine hydrochloride has applications in:

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;

For Ultraviolet–visible spectroscopy applications, Tris(2-carboxyethyl)phosphine hydrochloride is useful when it is important to avoid interfering absorbance from 250 to 285 nanometers which can occur with dithiothreitol. Dithiothreitol will slowly over time absorb more and more light in this spectrum as various redox reactions occur.

Hazards

Tris(2-carboxyethyl)phosphine hydrochloride is danger, it causes severe skin burns and eye damage, it may cause respiratory irritation.

Incompatibility

Incompatible Materials. Strong oxidizing agents. Halogens.

Storage

Keep refrigerated. Store contents under argon. Keep containers tightly closed in a dry, cool and well-ventilated place.