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C4706

Sigma-Aldrich

Tris(2-carboxyethyl)phosphine hydrochloride

powder

Synonym(s):

TCEP

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About This Item

Empirical Formula (Hill Notation):
C9H15O6P · HCl
CAS Number:
51805-45-9
Molecular Weight:
286.65
Beilstein:
3724376
MDL number:
MFCD00145469
UNSPSC Code:
12352128
PubChem Substance ID:
57654018
NACRES:
NA.22

description

Protect from moisture

Quality Level

300

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.

Caution

Storage conditions:protect from moisture.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Burns, J. A., et al.
The Journal of Organic Chemistry, 56, 1648-1648 (1991)
Selective reduction of disulfides by tris (2-carboxyethyl) phosphine.
Burns JA, et al.
The Journal of Organic Chemistry, 56(8), 2648-2650 (1991)
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)
Maynard, H. D.; Grubbs, R. J.
Tetrahedron Letters, 40, 4137-4137 (1999)
Andrea Krapp et al.
Cell reports, 26(4), 1044-1058 (2019-01-24)
Meiotic progression in S. pombe is regulated by stage-specific gene expression and translation, changes in RNA stability, expression of anti-sense transcripts, and targeted proteolysis of regulatory proteins. We have used SILAC labeling to examine the relative levels of proteins in diploid
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