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T84603

Sigma-Aldrich

Triphenylphosphine oxide

98%

Sinônimo(s):

Ph3PO, TPPO, Triphenyl phosphorus oxide, Triphenylphosphine monoxide

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About This Item

Fórmula linear:
(C6H5)3PO
Número CAS:
791-28-6
Peso molecular:
278.28
Beilstein:
745854
Número CE:
212-338-8
Número MDL:
MFCD00002080
Código UNSPSC:
12352002
ID de substância PubChem:
24900532
NACRES:
NA.22

Ensaio

98%

adequação da reação

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

pf

150-157 °C (lit.)

grupo funcional

phosphine oxide

cadeia de caracteres SMILES

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

chave InChI

FIQMHBFVRAXMOP-UHFFFAOYSA-N

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Aplicação

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.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H302,H412

Declarações de precaução

P264 - P270 - P273 - P301 + P312 - P501

Classificações de perigo

Acute Tox. 4 Oral - Aquatic Chronic 3

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 2

Ponto de fulgor (°F)

356.0 °F

Ponto de fulgor (°C)

180 °C

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análise (COA)

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Triphenylphosphine oxide-catalyzed stereoselective poly-and dibromination of unsaturated compounds
Yu T, et al.
Chemical Communications (Cambridge, England), 50(58), 7817-7820 (2014)
Phosphine oxide-catalysed chlorination reactions of alcohols under Appel conditions
Denton RM, et al.
Chemical Communications (Cambridge, England), 46(17), 3025-3027 (2010)
B H Lipshutz et al.
Organic letters, 3(12), 1869-1871 (2001-06-19)
[see reaction]. A simple, highly effective method for removing triphenylphosphine and/or triphenylphosphine oxide from reaction mixtures is described. Commercially available high-loading chloromethylated polystyrene 1, modified in situ with NaI, acts as a scavenger resin. Several coupling reactions catalyzed by Pd(0)
Stephen M Richoll et al.
Journal of chromatography. A, 1127(1-2), 147-153 (2006-07-04)
A versatile procedure has been developed and validated for the determination of triphenylphosphine oxide (TPPO) at low levels in various active pharmaceutical ingredients (APIs). This procedure incorporates the use of the novel hollow-fiber liquid-phase microextraction (LPME) for the measurement of
S Takeda et al.
Anticancer research, 13(1), 193-199 (1993-01-01)
We have investigated the nature of lipid peroxidation occurring in association with cancer-killing produced by gamma-linolenic acid (GLA) and iron (Fe) in cultured human breast cancer cells (ZR-75-1: ZR). UV-spectrophotometry, high performance liquid chromatography (HPLC) and gas chromatography (GC) or
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