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C4706 Aldrich

Tris(2-carboxyethyl)phosphine hydrochloride

powder, ≥98%

Synonym: TCEP



Frequently Asked Questions

Frequently Asked Questions are available for this Product.


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

Reagent for the selective reduction of disulfides in water.

Tris(2-carboxyethyl)phosphine hydrochloride (TCEP.HCl) may be employed as catalyst for the reduction of sulfoxides, sulfonyl chlorides, N-oxides, and azides.1 It may be used as reducing agent for the reduction of various alkyl disulfides such as trans-4,5-dihydroxy-1,2-dithiane.

When basified, this water-soluble ligand allows for simple removal of ruthenium-derived metathesis catalysts via aqueous washing of a crude reaction mixture.


2, 10, 50 g in glass bottle

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.1 TCEP is a useful chelating agent for various heavy metal ions as Zn(II), Cd(II), Pb(II), and Ni(II).

Price and Availability

LC-MS Grade Solvents and Reagents

Ultrafree Centrifugal Filter Units
Safety & Documentation

Safety Information

GHS05  GHS05
Signal word 
Hazard statements 
Precautionary statements 
UN 3261 8 / PGII
WGK Germany 

Frequently Asked Questions

Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis. These documents are located on the product detail page under Useful Links & Tools. Click on the following link to search for a Certificate of Analysis. Please click the following link to see the details on our Product Dating Information.
How do I get lot-specific information or a Certificate of Analysis?
A Certificate of Analysis is available by lot number and can be obtained through our Advanced Search Option: http://www.sigmaaldrich.com/catalog/AdvancedSearchPage.do
What is the primary function of Product C4706, Tris(2-carboxyethyl)phosphine hydrochloride?
Tris (2-carboxyethyl) phosphine hydrochloride (TCEP, #C4706) is capable of selectively cleaving disulfide bonds.
What is Product C4706, Tris(2-carboxyethyl)phosphine hydrochloride, soluble in?  
TCEP is soluble in water at 50 mg/ml and is also stable under both acidic and basic pH conditions. For work in protein analysis and mass spectrometry, we also offer an already prepared version of TCEP in a buffered aqueous solution. Product# 646547 is 0.5M solution of TCEP in water, where the pH has been adjusted to 7 with ammonium hydroxide.
What is the benefit of Product C4706, Tris(2-carboxyethyl)phosphine hydrochloride (TCEP), over traditional disulfide reduction agents, like DTT (dithiothreitol) and BME (beta-mercaptoethanol)?
TCEP is a very effective disulfide reducing agent that is less toxic than beta-mercaptoethanol and more stable to solution oxidation and pH changes than dithiothreitol.
Where can I find a list of other reducing agents for protein analysis?
The following link will provide information on other reducing agents for protein analysis: http://www.sigmaaldrich.com/Area_of_Interest/Life_Science/Proteomics_and_Protein_Expr_/Proteomics/Sample_Preparation/Individual_Reagents/Reducing_agents.html
Where can I find protocols that cite the use of Product C4706, Tris(2-carboxyethyl)phosphine hydrochloride (TCEP)?
We have several protocols citing the use of TCEP available through Cold Spring Harbor Laboratory Press. I. “Direct Enzymatic Digestion of Protein Complexes” is available through the link below. http://www.sigmaaldrich.com/Area_of_Interest/Life_Science/Proteomics_and_Protein_Expr/Protein_Expression/Enzymatic_Digestion_of_Protein_Complexes.html II. “Digestion of Proteins and Extractions of Peptides from an Acrylamide Gel” is available through the link below. http://www.sigmaaldrich.com/Area_of_Interest/Life_Science/Proteomics_and_Protein_Expr/Protein_Expression/Proteomics_Protocol_Digestion.html III. In addition to the protocols available through Cold Spring Harbor Laboratory Press, we have additional references below. 1. Burns, J. A., et al. J. Org. Chem. 56, 1648, (1991) 2. Maynard, H. D.; Grubbs, R. J. Tet. Lett. 40, 4137, (1999) 3. Grubbs, R. H. Org. React. 22, 123, (2004) 4. Burns, J.A. J. Org. Chem. 56, 2648, (1991) 5. Kirley, T.L., Reduction and fluorescent labeling of cyst(e)ine-containing proteins for subsequent structural analyses. Anal. Biochem. 180, 231-236, (1989) 6. Fischer W.H, et al., In situ reduction suitable for matrix-assisted laser desorption/ionization and liquid secondary ionization using tris(2-carboxyethyl)phosphine. Rapid Commun. Mass Spectrom. 7, 225-228, (1993) 7. Getz, E.B., et al., A comparison between the sulfhydryl reductants tris(2-carboxyethyl)phosphine and dithiothreitol for use in protein biochemistry. Anal. Biochem. 273, 73-80, (1999)  8. Beil. 4,IV,3441
How do I find price and availability?
There are several ways to find pricing and availability for our products.  Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers. 
What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS. To access the shipping information for this material, use the link on the product detail page for the product, or search here. 
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Protocols & Articles


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75259 Tris(2-carboxyethyl)phosphine hydrochloride, BioUltra, ≥98% (NMR)
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