ChemicalBook > CAS DataBase List > Tris(2-carboxyethyl)phosphine hydrochloride

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
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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)
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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
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
68957
Product name
Tris(2-carboxyethyl)phosphine hydrochloride
Purity
BioUltra, for electrophoresis, SDS-PAGE tested
Packaging
10g
Price
$1110
Updated
2024/03/01
Sigma-Aldrich
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
$132
Updated
2024/03/01
Sigma-Aldrich
Product number
580567
Product name
TCEP,Hydrochloride,ReagentGrade-CAS51805-45-9-Calbiochem
Packaging
5G
Price
$338
Updated
2024/03/01
Sigma-Aldrich
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
$122
Updated
2022/05/15
TCI Chemical
Product number
T1656
Product name
Tris(2-carboxyethyl)phosphine Hydrochloride
Purity
>98.0%(T)
Packaging
1g
Price
$53
Updated
2024/03/01
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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.

Biochem/physiol Actions

Tris(2-carboxyethyl)phosphine hydrochloride solution reduces the disulfide bonds and leaves other functional groups intact in proteins.

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) Fischer?et al.?(1993),?In situ reduction suitable for matrix-assisted laser desorption/ionization and liquid secondary ionization using tris(2-carboxyethyl)phosphine; Rapid Commun. Mass Spectrom.,?7?225 2) Kirley?et al.?(1989),?Reduction and fluorescent labeling of cyst(e)ine-containing proteins for subsequent structural analysis; Anal. Biochem.,?180?231 3) Getz?et al. (1999),?A comparison between the sulfhydryl reductants tris(2-carboxyethyl)phosphine and dithiothreitol for use in protein biochemistry; Anal. Biochem.,?273?73

Tris(2-carboxyethyl)phosphine hydrochloride Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Tris(2-carboxyethyl)phosphine hydrochloride manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
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
WUHAN FORTUNA CHEMICAL CO., LTD
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
Apeloa production Co.,Limited
Product
Tris(2-carboxyethyl)phosphine Hydrochloride 51805-45-9
Price
US $1.00/g
Min. Order
1g
Purity
99%
Supply Ability
3000
Release date
2024-06-05

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