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C4706

Sigma-Aldrich

Tris(2-carboxyethyl)phosphine hydrochloride

powder

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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

description

Protect from moisture

Quality Level

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

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible, corrosive hazardous materials

wgk_germany

WGK 1

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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Protocols

Overcome challenges in synthesis and disulfide bond formation with protocols for Fmoc solid-phase peptide synthesis of peptides with cysteine and methionine.

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