C4706

Sigma-Aldrich

Tris(2-carboxyethyl)phosphine hydrochloride

powder

Synonym(s):
TCEP
Empirical Formula (Hill Notation):
C9H15O6P · HCl
CAS Number:
Molecular Weight:
286.65
Beilstein/REAXYS Number:
3724376
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

description

Protect from moisture

form

powder

reaction suitability

reagent type: reductant

color

white

solubility

H2O: 50 mg/mL

storage temp.

2-8°C

SMILES string

Cl[H].OC(=O)CCP(CCC(O)=O)CCC(O)=O

InChI

1S/C9H15O6P.ClH/c10-7(11)1-4-16(5-2-8(12)13)6-3-9(14)15;/h1-6H2,(H,10,11)(H,12,13)(H,14,15);1H

InChI key

PBVAJRFEEOIAGW-UHFFFAOYSA-N

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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).

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.

Packaging

2, 10, 50 g in glass bottle

Caution

Storage conditions:protect from moisture.

pictograms

Corrosion

signalword

Danger

hcodes

hazcat

Eye Dam. 1 - Skin Corr. 1B

storage_class_code

8A - Combustible, corrosive hazardous materials

WGK Germany

WGK 1

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

  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

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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. 

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Selective reduction of disulfides by tris(2-carboxyethyl)phosphine
Burns, J. A., et al.
The Journal of Organic Chemistry, 56(8), 2648-2648 (1991)
Selective reduction of disulfides by tris (2-carboxyethyl) phosphine.
Burns JA, et al.
The Journal of Organic Chemistry, 56(8), 2648-2650 (1991)
Grubbs, R. H.
Org. React., 22, 123-123 (2004)
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)
Purification technique for the removal of ruthenium from olefin metathesis reaction products
Maynard, H. D.; Grubbs, R. J.
Tetrahedron Letters, 40, 4137-4137 (1999)
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