C4706
Tris(2-carboxyethyl)phosphine hydrochloride
powder
Synonym(s):
TCEP
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About This Item
Empirical Formula (Hill Notation):
C9H15O6P · HCl
CAS Number:
Molecular Weight:
286.65
Beilstein:
3724376
MDL number:
UNSPSC Code:
12352128
PubChem Substance ID:
NACRES:
NA.22
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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.
related product
Signal Word
Danger
Hazard Statements
Precautionary Statements
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
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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.
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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.
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Maynard, H. D.; Grubbs, R. J.
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