Basic information
- CAS
51805-45-9- Standard SMILES
Cl.O=C(O)CCP(CCC(=O)O)CCC(=O)O- InChIKey
PBVAJRFEEOIAGW-UHFFFAOYSA-N- Molecular formula
- C9H16ClO6P
- Average molar mass
- 286.64 g/mol
- Monoisotopic mass
- 286.0373029
Names & identifiers
- Preferred name
- Tris(2-carboxyethyl)phosphine hydrochloride
- IUPAC
- 3-[bis(2-carboxyethyl)phosphanyl]propanoic acid;hydrochloride
- English name
- Tris(2-carboxyethyl)phosphine hydrochloride
- Molecular formula
- C9H15O6P.ClH
- Molecular weight
- 286.65
Names & synonyms
51805-45-9Tris(2-carboxyethyl)phosphine hydrochlorideTCEP HydrochlorideTCEP HClTcep hydrochloride [MI]UNII-H49AAM893KH49AAM893KDTXSID10370367Propanoic acid, 3,3',3''-phosphinylidynetris-, hydrochloride (1:1)RefChem:192079DTXCID80321402629-759-1
Show more names
TRI(2-CARBOXYETHYL)PHOSPHINE HYDROCHLORIDETCEP-HCITCEP SolutionTCEP, HYDROCHLORIDETris(2-carboxyethyl)phosphine hydrochloride, 98% 1GRTCEP*HCL0.5M TCEP500 MM TCEP
3,3',3''-Phosphinetriyltripropanoic acid hydrochlorideMFCD00145469TCEP (hydrochloride)3-[bis(2-carboxyethyl)phosphanyl]propanoic acid;hydrochlorideC9H16ClO6PTris(carboxyethyl)phosphine hydrochloridetris-(2-carboxyethyl)phosphine hydrochloride3-[bis(2-carboxyethyl)phosphanyl]propanoic acid hydrochloride
Database identifiers
- CAS
51805-45-9- PubChem CID
- 2734570
- DTXSID
Properties
Computed structural properties
- Topological polar surface area
- 112 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 9
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 222
Physicochemical properties
- Melting point
- 177 °C · 177 °C
- Density
- 1.041 g/mL · 1.041 g/mL at 25 °C
- refractive index
- 20 · n20/D 1.367
- storage temp.
- 2 · 2-8°C
- solubility
- 2 O: · H2O: 50 mg/mL
- form
- powder
- pka
- 7.66 · 7.66(at 25℃)
- color
- white
- PH
- 7 · 7.0(aqueous solution; pH was adjusted with ammonium hydroxide)
- Water Solubility
- Soluble in water and methanol.
- Sensitive
- Moisture Sensitive
- λmax
- 260 nm · λ: 260 nm Amax: 0.05λ: 280 nm Amax: 0.03
- Merck
- 14 · 14,9085
- BRN
- 3724376 · 3724376
- Stability
- 1 year · 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.
- 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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H314 (98.2%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]；H318 (15.9%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 226 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Hazard Classes and CategoriesSkin Corr. 1A (98.2%)；Eye Dam. 1 (15.9%)
Safety data
- F
- 10
- wgk
- 2
- tsca
- No
- ridadr
- UN 3261 8/PG 2
- hs_code
- 29319090
- risk_code
- 36/38-36/37/38-34
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- C,Xi
- safety_code
- 26-37/39-36/37/39-27-45
- hazard_class
- 8
Chemistry & industry
Applications
DescriptionTCEP HCl (51805-45-9) is a reagent for selective reduction of disulfides in aqueous solutions1-3with 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
UsesTCEP (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.
UsesReducing 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.
UsesBiochemical tool for selective reduction of disulfide bridges at low pH; reductant for redox assays.
General DescriptionTris (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.
Preparation methods
PreparationThe 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%
Related reactions
8 records
Compound notes
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