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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:
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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description

Protect from moisture

Quality Segment

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 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

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

Disclaimer

Storage conditions:protect from moisture.

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pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

C4706-2G: + C4706-BULK: + C4706-10G: + C4706-VAR: + C4706-50G:

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