C4706

Tris(2-carboxyethyl)phosphine hydrochloride

powder

• Synonym(s): TCEP
• Empirical Formula (Hill Notation): C₉H₁₅O₆P · HCl
• CAS Number: 51805-45-9
• Molecular Weight: 286.65
• Beilstein/REAXYS Number: 3724376
• MDL number: MFCD00145469
• UNSPSC Code: 12352128
• PubChem Substance ID: 57654018
• NACRES: NA.22

Properties

• description: Protect from moisture
• Quality Level: 300
• 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

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.

Caution

Storage conditions:protect from moisture.

Safety Information

• pictograms: GHS05
• signalword: Danger
• hcodes: H314
• pcodes: P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363
• 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