Tris(2-carboxyethyl)phosphine hydrochloride
- Product Name
- Tris(2-carboxyethyl)phosphine hydrochloride
- CAS No.
- 51805-45-9
- Chemical Name
- Tris(2-carboxyethyl)phosphine hydrochloride
- Synonyms
- TCEP HCL;TCEP Solution;Tris(2-carboxyethyl)phosphine hydrochloride, 98% 1GR;TCEP*HCL;TCEP-HCI;0.5M TCEP;500 MM TCEP;TCEP, HYDROCHLORIDE;)phosphine hydrochL;TCEP-HCl, OMniPur(R)
- CBNumber
- CB8263816
- Molecular Formula
- C9H15O6P.ClH
- Formula Weight
- 286.65
- MOL File
- 51805-45-9.mol
Tris(2-carboxyethyl)phosphine hydrochloride Property
- Melting point:
- 177 °C
- Density
- 1.041 g/mL at 25 °C
- refractive index
- n20/D 1.367
- storage temp.
- 2-8°C
- solubility
- H2O: 50 mg/mL
- form
- powder
- pka
- 7.66(at 25℃)
- color
- white
- PH
- 7.0(aqueous solution; pH was adjusted with ammonium hydroxide)
- Water Solubility
- Soluble in water and methanol.
- Sensitive
- Moisture Sensitive
- λmax
- λ: 260 nm Amax: 0.05
λ: 280 nm Amax: 0.03 - Merck
- 14,9085
- BRN
- 3724376
- Stability:
- Stable for 1 year from date of purchase as supplied. Solutions in distilled water may be stored at -20°C for up to 1 month.
- InChIKey
- PBVAJRFEEOIAGW-UHFFFAOYSA-N
- CAS DataBase Reference
- 51805-45-9(CAS DataBase Reference)
Safety
- Hazard Codes
- C,Xi
- Risk Statements
- 36/38-36/37/38-34
- Safety Statements
- 26-37/39-36/37/39-27-45
- RIDADR
- UN 3261 8/PG 2
- WGK Germany
- 2
- F
- 10
- TSCA
- No
- HazardClass
- 8
- PackingGroup
- III
- HS Code
- 29319090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H314Causes severe skin burns and eye damage
- Precautionary statements
-
P260Do not breathe dust/fume/gas/mist/vapours/spray.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 68957
- Product name
- Tris(2-carboxyethyl)phosphine hydrochloride
- Purity
- BioUltra, for electrophoresis, SDS-PAGE tested
- Packaging
- 10g
- Price
- $1150
- Updated
- 2025/07/31
- Product number
- 646547
- Product name
- Tris(2-carboxyethyl)phosphine hydrochloride solution
- Purity
- 0.5 M, pH 7.0(aqueous solution; pH was adjusted with ammonium hydroxide)
- Packaging
- 10x1ml
- Price
- $139
- Updated
- 2025/07/31
- Product number
- 580567
- Product name
- TCEP,Hydrochloride,ReagentGrade-CAS51805-45-9-Calbiochem
- Packaging
- 5G
- Price
- $359
- Updated
- 2025/07/31
- Product number
- 580560
- Product name
- TCEP, Hydrochloride - CAS 51805-45-9 - Calbiochem
- Purity
- A water-soluble and odorless disulfide-reducing agent that is more stable and effective than DTT.
- Packaging
- 1G
- Price
- $151
- Updated
- 2025/07/31
- Product number
- T1656
- Product name
- Tris(2-carboxyethyl)phosphine Hydrochloride
- Purity
- >98.0%(T)
- Packaging
- 1g
- Price
- $53
- Updated
- 2025/07/31
Tris(2-carboxyethyl)phosphine hydrochloride Chemical Properties,Usage,Production
Description
TCEP HCl (51805-45-9) is a reagent for selective reduction of disulfides in aqueous solutions1-3?with distinct advantages over DTT which are application specific3. For example, spin labels are more stable with TCEP than DTT, Ni2+?(leached from affinity columns) causes rapid oxidation of DTT with no effect on TCEP and for long term storage of proteins TCEP is more stable than DTT with no metal chelator (EGTA) present but DTT is more stable in the presence of metal chelators.3
Chemical Properties
White Crystalline Solid
Uses
TCEP (Tris(2-carboxyethyl)phosphine hydrochloride) is an alternative which is not pungent, more stable and works even at low pH. It is more selective, i.e. do not reduce metals and buried disulfides.
Uses
Reducing agent, specific for disulfidesTris(2-carboxyethyl)phosphine hydrochloride is widely used as a reducing agent to reduce disulfide bonds in proteins and trans-4,5-dihydroxy-1,2-dithiane. It is involved in the reduction of sulfoxides, sulfonyl chlorides, N-oxides, and azides. It plays an important role in the tissue homogenization process for RNA isolation. It acts as a chelating agent and forms complexes with various heavy metal ions such as Zn(II), Cd(II), Pb(II), and Ni(II). Furthermore, it is useful in the labeling of cysteine residues with maleimides.
Uses
Biochemical tool for selective reduction of disulfide bridges at low pH; reductant for redox assays.
Preparation
The preparation of Tris(2-carboxyethyl)phosphine hydrochloride is as follows:Trimethyl 3,3 ', 3 "-phosphine triphenylpropionate (92.5g, 0.28mol) prepared as described above was added to a 250 ml reaction flask under mechanical stirring conditions and a molar ratio of 12mol/(120ml, 1.44mol), the mixture was heated to 90°C, the solid gradually dissolved, continue to heat the reaction 4h, stirring and cooling with ice water, precipitation of white solid, filter, filter cake with distilled water to get white (2-carboxyethyl) phosphine hydrochloride, dried, weighing 61.3g, yield 82.4%
General Description
Tris (2-carboxyethyl) phosphine (TCEP) is very effective in cleaving disulfide bonds in aqueous solution. It dissolves in water and is odorless, unlike other trialkylphosphines (tributylphosphine). It is also less toxic than 2-mercaptoethanol. These advantages make it better than the other reducing agents.
Reactivity Profile
Nucleophilic Substitution by the Phosphorus Atom of TCEP. 1. The phosphorus atom attacks one sulfur atom along the S-S bond. 2. A thioalkoxyphosphonium cation and a sulfhydryl anion are formed. 3. A rapid hydrolysis releases the second sulfhydryl molecule and the phosphine oxide. There are two main steps in the breaking of disulfide bridges and forming a free sulfhydryl using TCEP: cleavage of the S-S bond; oxidation of the phosphine and release of sulfhydryl.
reaction suitability
reagent type: reductant
Biochem/physiol Actions
Tris(2-carboxyethyl)phosphine hydrochloride solution reduces the disulfide bonds and leaves other functional groups intact in proteins.
Synthesis
67991-12-2
51805-45-9
The general procedure for the synthesis of tris(2-carbonylethyl)phosphine hydrochloride from triethyl 3,3',3''-phosphinotriphenylpropionate was as follows: pre-prepared trimethyl 3,3',3''-phosphinotriphenylpropionate (92.5 g, 0.28 mol) was placed in a 250 ml reaction flask, and hydrochloric acid (120 ml, 1.44 mol) in a 12:1 molar ratio was added under mechanical stirring ). The reaction mixture was heated to 90°C until the solid was completely dissolved and the reaction was continued at this temperature for 4 hours. After completion of the reaction, it was cooled in an ice water bath and stirred to precipitate a white solid. The solid was separated by filtration and the filter cake was washed with distilled water to give white tris(2-carboxyethyl)phosphorus hydrochloride. The product was dried and weighed 61.3 g with a yield of 82.4%.
storage
Following reconstitution, aliquot and freeze (-20°C). TCEP retains stability when stored at an acidic or alkaline pH; avoid storage at pH 7.0-8.0. Also avoid exposure to high concentrations of phosphate ions (>150 mM). Stock solutions are stable for up to 3 months at -20°C.
References
[1] WOLFGANG H. FISCHER A. G C Jean E Rivier. In situ reduction suitable for matrix-assisted laser desorption/ionization and liquid secondary ionization using tris(2-carboxyethyl)phosphine[J]. Rapid Communications in Mass Spectrometry, 1993, 7 3: 225-228. DOI:10.1002/rcm.1290070312
[2] KIRLEY T L. Reduction and fluorescent labeling of cyst(e)ine-containing proteins for subsequent structural analyses[J]. Analytical biochemistry, 1989, 180 2: Pages 231-236. DOI:10.1016/0003-2697(89)90422-3
[3] ELISE BURMEISTER GETZ . A Comparison between the Sulfhydryl Reductants Tris(2-carboxyethyl)phosphine and Dithiothreitol for Use in Protein Biochemistry[J]. Analytical biochemistry, 1999, 273 1: Pages 73-80. DOI:10.1006/abio.1999.4203
Tris(2-carboxyethyl)phosphine hydrochloride Preparation Products And Raw materials
Raw materials
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View Lastest Price from Tris(2-carboxyethyl)phosphine hydrochloride manufacturers
- Product
- Tris(2-carboxyethyl)phosphine Hydrochloride 51805-45-9
- Price
- US $0.00-0.00/kg
- Min. Order
- 100kg
- Purity
- 98%min
- Supply Ability
- 50kg
- Release date
- 2024-06-03
- Product
- Tris(2-carboxyethyl)phosphine hydrochloride 51805-45-9
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 500000kg
- Release date
- 2024-10-25
- Product
- Tris(2-carboxyethyl)phosphine hydrochloride 51805-45-9
- Price
- US $10.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20ton
- Release date
- 2024-05-21