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Merck
CN

T84603

Triphenylphosphine oxide

greener alternative

98%

Synonym(s):

Ph3PO, TPPO, Triphenyl phosphorus oxide, Triphenylphosphine monoxide

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About This Item

Linear Formula:
(C6H5)3PO
CAS Number:
Molecular Weight:
278.28
UNSPSC Code:
12352002
NACRES:
NA.22
PubChem Substance ID:
EC Number:
212-338-8
Beilstein/REAXYS Number:
745854
MDL number:
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Quality Level

assay

98%

reaction suitability

reagent type: ligand
reaction type: Coupling Reactions, reagent type: ligand
reaction type: Epoxidations, reagent type: ligand
reaction type: Michael Reaction

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

150-157 °C (lit.)

functional group

phosphine oxide

greener alternative category

SMILES string

O=P(c1ccccc1)(c2ccccc2)c3ccccc3

InChI

1S/C18H15OP/c19-20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H

InChI key

FIQMHBFVRAXMOP-UHFFFAOYSA-N

General description

We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives. This product falls under category 12 PAP and aligns with the Green Chemistry Principle of Catalysis. Click here for more information.

Application

Triphenylphosphine oxide can be used:
  • As a catalyst in Appel-type chlorination reaction of acyclic primary and secondary alcohols.
  • As a catalyst in stereoselective poly and dibromination of α,β-unsaturated esters and β,γ-unsaturated α-ketoester compounds.
  • As a promotor in the diastereoselective synthesis of α-ribofuranosides through ribofuranosylation of alcohols with ribofuranosyl iodides.



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Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

356.0 °F

flash_point_c

180 °C

ppe

dust mask type N95 (US), Eyeshields, Gloves



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Related Content

Phosphine Ligand Application Guide


?-Selective Ribofuranosylation of Alcohols with Ribofuranosyl Iodides and Triphenylphosphine Oxide
Oka N, et al.
The Journal of Organic Chemistry, 79(16), 7656-7664 (2014)
Phosphine oxide-catalysed chlorination reactions of alcohols under Appel conditions
Denton RM, et al.
Chemical Communications (Cambridge, England), 46(17), 3025-3027 (2010)
Triphenylphosphine oxide-catalyzed stereoselective poly-and dibromination of unsaturated compounds
Yu T, et al.
Chemical Communications (Cambridge, England), 50(58), 7817-7820 (2014)



Global Trade Item Number

SKUGTIN
T84603-25G04061835559862
T84603-100G04061835559855