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Tris(2-carboxyethyl)phosphine hydrochloride


Empirical Formula (Hill Notation):
C9H15O6P · HCl
CAS Number:
Molecular Weight:
MDL number:
PubChem Substance ID:

Quality Level


Protect from moisture



reaction suitability

reagent type: reductant




H2O: 50 mg/mL

storage temp.


SMILES string




InChI key


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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).


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.


2, 10, 50 g in glass bottle


Storage conditions:protect from moisture.



Signal Word


Hazard Statements

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible, corrosive hazardous materials



Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

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Product Information Sheet

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Quotes and Ordering

  1. 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.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. 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.

  4. 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.

  5. 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.

  6. Where can I find protocols that cite the use of Product C4706, Tris(2-carboxyethyl)phosphine hydrochloride (TCEP)?

    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

  7. How do I find price and availability?

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  8. 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. 

  9. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Grubbs, R. H.
Org. React., 22, 123-123 (2004)
Selective reduction of disulfides by tris (2-carboxyethyl) phosphine.
Burns JA, et al.
The Journal of Organic Chemistry, 56(8), 2648-2650 (1991)
Selective reduction of disulfides by tris(2-carboxyethyl)phosphine
Burns, J. A., et al.
The Journal of Organic Chemistry, 56(8), 2648-2648 (1991)
Tris (2-carboxyethyl) phosphine Hydrochloride
Yost Julianne M et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 1-9 (2001)
Coordination properties of tris (2-carboxyethyl) phosphine, a newly introduced thiol reductant, and its oxide.
Krezel A, et al.
Inorganic Chemistry, 42(6), 1994-2003 (2003)


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