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C4706

Tris(2-carboxyethyl)phosphine hydrochloride

Name: Tris(2-carboxyethyl)phosphine hydrochloride
Brand: ALDRICH

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

UNSPSC Code:

12352128

NACRES:

NA.22

PubChem Substance ID:

57654018

MDL number:

MFCD00145469

Beilstein/REAXYS Number:

3724376

Form:

powder

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Properties

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

Description

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.