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
UNSPSC Code:
12352128
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3724376
Form:
powder
description
Protect from moisture
Quality Segment
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 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.
Disclaimer
Storage conditions:protect from moisture.
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signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1 - Skin Corr. 1B
Storage Class
8A - Combustible corrosive hazardous materials
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
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