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文件

C4706

Sigma-Aldrich

三 2-羰基乙基 磷盐酸盐 盐酸盐

powder

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别名:
TCEP
经验公式（希尔记法）:
C9H15O6P · HCl
CAS号:
51805-45-9
分子量:
286.65
Beilstein:
3724376
MDL编号:
MFCD00145469
PubChem化学物质编号:
57654018
NACRES:
NA.22

描述

Protect from moisture

质量水平

200

形式

powder

反应适用性

reagent type: reductant

颜色

white

溶解性

H2O: 50 mg/mL

储存温度

2-8°C

SMILES字符串

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

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相关类别

一般描述

三（2-羧乙基）膦盐酸（TCEP.HCl）是一种非挥发性的固体。它是一种强还原剂。1可通过回流HCl水溶液水解三（2-氰基乙基）膦酸合成。1 它支持多种生物学应用，如体外和体内还原各种肽和蛋白质中的二硫键。TCEP是适于各种重金属离子的重要螯合剂，如Zn(II)、Cd(II)、Pb(II)和Ni(II)。

应用

三(2-羧乙基)膦盐酸盐(TCEP.HCl)可用于：
  • 用作还原亚砜、磺酰氯、N-氧化物和叠氮化物的还原剂。存在铜催化剂的条件下，它还可用于叠氮化物-炔烃的环加成反应。
  • 还原各种蛋白质中的二硫键。
  • 用作选择性还原水中二硫化物的试剂。
  • 碱化粗反应混合物时，通过水洗除去钌衍生的复分解催化剂。
  • 用作还原各种烷基二硫键的还原剂，例如反式-4,5-二羟基-1,2-二噻烷。
水溶性试剂，用于二硫化物的选择性还原。在质谱应用中比 DTT 更稳定。

注意

储存条件：干燥储存。

相关产品

产品编号
说明
价格

象形图

Corrosion
GHS05

警示用语：

Danger

危险声明

H314

危险分类

Eye Dam. 1 - Skin Corr. 1B

储存分类代码

8A - Combustible, corrosive hazardous materials

WGK

WGK 1

个人防护装备

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

分析证书(COA)

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索取COA

  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What is the primary function of Product C4706, Tris(2-carboxyethyl)phosphine hydrochloride?

    Tris (2-carboxyethyl) phosphine hydrochloride (TCEP, #C4706) is capable of selectively cleaving disulfide bonds.

  4. What is Product C4706, Tris(2-carboxyethyl)phosphine hydrochloride, soluble in? 

    TCEP is soluble in water at 50 mg/ml and is also stable under both acidic and basic pH conditions. For work in protein analysis and mass spectrometry, we also offer an already prepared version of TCEP in a buffered aqueous solution. Product# 646547 is 0.5M solution of TCEP in water, where the pH has been adjusted to 7 with ammonium hydroxide.

  5. What is the benefit of Product C4706, Tris(2-carboxyethyl)phosphine hydrochloride (TCEP), over traditional disulfide reduction agents, like DTT (dithiothreitol) and BME (beta-mercaptoethanol)?

    TCEP is a very effective disulfide reducing agent that is less toxic than beta-mercaptoethanol and more stable to solution oxidation and pH changes than dithiothreitol.

  6. Where can I find protocols that cite the use of Product C4706, Tris(2-carboxyethyl)phosphine hydrochloride (TCEP)?

    1. Burns, J. A., et al. J. Org. Chem. 56, 1648, (1991)2. Maynard, H. D.; Grubbs, R. J. Tet. Lett. 40, 4137, (1999)3. Grubbs, R. H. Org. React. 22, 123, (2004)4. Burns, J.A. J. Org. Chem. 56, 2648, (1991)5. Kirley, T.L., Reduction and fluorescent labeling of cyst(e)ine-containing proteins for subsequent structural analyses. Anal. Biochem. 180, 231-236, (1989)6. Fischer W.H, et al., In situ reduction suitable for matrix-assisted laser desorption/ionization and liquid secondary ionization using tris(2-carboxyethyl)phosphine. Rapid Commun. Mass Spectrom. 7, 225-228, (1993)7. Getz, E.B., et al., A comparison between the sulfhydryl reductants tris(2-carboxyethyl)phosphine and dithiothreitol for use in protein biochemistry. Anal. Biochem. 273, 73-80, (1999) 8. Beil. 4,IV,3441

  7. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  8. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  9. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Grubbs, R. H.
Org. React., 22, 123-123 (2004)
Selective reduction of disulfides by tris (2-carboxyethyl) phosphine.
Burns JA, et al.
The Journal of Organic Chemistry, 56(8), 2648-2650 (1991)
Selective reduction of disulfides by tris(2-carboxyethyl)phosphine
Burns, J. A., et al.
The Journal of Organic Chemistry, 56(8), 2648-2648 (1991)
Coordination properties of tris (2-carboxyethyl) phosphine, a newly introduced thiol reductant, and its oxide.
Krezel A, et al.
Inorganic Chemistry, 42(6), 1994-2003 (2003)
Purification technique for the removal of ruthenium from olefin metathesis reaction products
Maynard, H. D.; Grubbs, R. J.
Tetrahedron Letters, 40, 4137-4137 (1999)
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