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777854

Sigma-Aldrich

Tris(hydroxypropyl)phosphine

≥80%

Synonym(s):

THPP

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1 G
€53.90
5 G
€164.00

About This Item

Empirical Formula (Hill Notation):
C9H21O3P
CAS Number:
4706-17-6
Molecular Weight:
208.24
MDL number:
MFCD00269835
UNSPSC Code:
12352128
PubChem Substance ID:
329767934
NACRES:
NA.22

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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

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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.[1]

Application

Tris(hydroxypropyl)phosphine can be used:
  • As a reducing agent in the reduction of dehydroascorbic acid to ascorbic acid[2]
  • In the cleavage of disulfide bonds in small molecules[3]
  • As a catalyst in the conversion of polysulfides[4]

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV6692
MKCX0120
MKCV9123
MKCV8655
MKCT3320

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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)
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.
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)
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)
Kristine Opsvik Wikene et al.
Journal of photochemistry and photobiology. B, Biology, 171, 27-33 (2017-05-05)
Natural deep eutectic solvents (NADES) are a third class of liquids, separate from water and lipids. Some NADES, especially those containing organic acids, have been suggested to possess antimicrobial properties. Such properties may be advantageous when NADES are used as
View All Related Papers

Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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