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Merck

777854

Sigma-Aldrich

Tris(hydroxypropyl)phosphine

≥80%

Sinónimos:

THPP

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About This Item

Fórmula empírica (notación de Hill):
C9H21O3P
Número de CAS:
Peso molecular:
208.24
MDL number:
UNSPSC Code:
12352128
PubChem Substance ID:
NACRES:
NA.22
form:
liquid
assay:
≥80%

Quality Level

assay

≥80%

form

liquid

reaction suitability

reagent type: reductant

density

1.136 g/mL at 25 °C

SMILES string

OCCCP(CCCO)CCCO

InChI

1S/C9H21O3P/c10-4-1-7-13(8-2-5-11)9-3-6-12/h10-12H,1-9H2

InChI key

YICAEXQYKBMDNH-UHFFFAOYSA-N

General description

Tris(hydroxypropyl)phosphine (THPP) is a reducing agent widely used for the reductive cleavage of disulfide bonds in small molecules in both aqueous–organic media.

Application

Tris(hydroxypropyl)phosphine can be used:
  • As a reducing agent in the reduction of dehydroascorbic acid to ascorbic acid
  • In the cleavage of disulfide bonds in small molecules
  • As a catalyst in the conversion of polysulfides

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Designing dendritic polymers containing phosphorus donor ligands and their corresponding transition metal complexes.
Dasgupta M, et al.
Coordination Chemistry Reviews, 233(19), 223-235 (2002)
Tris (3-hydroxypropyl) phosphine (THPP): A mild, air-stable reagent for the rapid, reductive cleavage of small-molecule disulfides.
McNulty J, et al.
Bioorganic & Medicinal Chemistry Letters, 25(19), 4114-4117 (2015)
One-Pot Peptide Ligation-Oxidative Cyclization Protocol for the Preparation of Short-/Medium-Size Disulfide Cyclopeptides.
Spengler J, et al.
Organic Letters, 20(14), 4306-4309 (2018)
Suttipong Suttapitugsakul et al.
Molecular bioSystems, 13(12), 2574-2582 (2017-10-12)
Mass spectrometry (MS) has become an increasingly important technique to analyze proteins. In popular bottom-up MS-based proteomics, reduction and alkylation are routine steps to facilitate peptide identification. However, incomplete reactions and side reactions may occur, which compromise the experimental results.
Hairong Wang et al.
Biomaterials, 181, 310-317 (2018-08-11)
Tumor hypoxia is known to be one of critical factors that aggravate the tumor resistance to photodynamic therapy (PDT) in which oxygen is essential for tumor destruction. Herein, catalase, an enzyme to trigger hydrogen peroxide (H2O2) decomposition, is modified by

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