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Sigma-Aldrich® Tris(2-carboxyethyl)phosphine hydrochloride

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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

mp  175-177 °C

solubility  H2O: 50 mg/mL

density  1.041 g/cm3 at 25 °C

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

General description

Tris(2-carboxyethyl)phosphine hydrochloride (TCEP.HCl) is a non-volatile solid. It is a strong reducing agent.1[1] It can be synthesized by the acid hydrolysis of tris(2-cyanoethyl)phosphine in refluxing aqueous HCl.1[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).[2]

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.[3]
  • To reduce disulfide bonds in various proteins.[3]
  • As a reagent for the selective reduction of disulfides in water.[1]
  • To remove ruthenium-derived metathesis catalysts via aqueous washing of a crude reaction mixture when it is basified.[4][5]
  • As a reducing agent for the reduction of various alkyl disulfides such as trans-4,5-dihydroxy-1,2-dithiane.[1]

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

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Storage conditions:protect from moisture.