(Metoxicarbonilmetilen)trifenilfosforano, 98 %, Thermo Scientific Chemicals

Name: (Metoxicarbonilmetilen)trifenilfosforano, 98 %, Thermo Scientific Chemicals
SKU: A14020.22
Price: 289.00 EUR

CAS: 2605-67-6 | C21H19O2P | 334.36 g/mol

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25 g

100 g

500 g

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Número de catálogo A14020.22

también denominado A14020-22

Precio (EUR)

289,00

Each

Cantidad:

100 g

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Precio (EUR)

289,00

Each

Identificadores químicos

CAS2605-67-6

IUPAC Namemethyl 2-(triphenyl-λ⁵-phosphanylidene)acetate

Molecular FormulaC21H19O2P

InChI KeyNTNUDYROPUKXNA-UHFFFAOYSA-N

SMILESCOC(=O)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1

Especificaciones Specification Sheet

Hoja de especificaciones

Assay (HPLC)≥97.5%

Melting Point (clear melt)164-171°C

Appearance (Color)White to pale cream or pale grey

FormPowder

(Methoxycarbonylmethylene)triphenylphosphorane is used in olefination reactions. Further, it undergoes the Wittig reaction with aldehydes to give substituted methyl acrylates. It is used in the preparation of (triphenylphosphoranylidene)-ketene.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Aplicaciones
El (metoxicarbonilmetilen)trifenilfosforano se utiliza en reacciones de olefinación. Además, se somete a la reacción de Wittig con aldehídos para producir metilacrilatos sustituidos. Se utiliza en la preparación de (trifenilfosforanilideno)-ceteno.

Solubilidad
Soluble en cloroformo. Ligeramente soluble en etanol y terahidrofurano. Insoluble en agua.

Notas
Sensible al aire. Incompatible con agentes oxidantes fuertes.

RUO – Research Use Only

General References:

Stable ylide which undergoes the Wittig reaction with aldehydes to give substituted methyl acrylates. See also (Ethoxycarbonyl methyl ene) triphenyl phosphorane, A12896 and Appendix 1. For a detailed study of the reaction with benzaldehyde, see J. Org. Chem., 59, 1126 (1994). For use of high pressure to increase the yield and trans-selectivity of reaction with aromatic aldehydes, see: Liebigs Ann. Chem., 2135 (1983).
For tandem Wittig reaction and Cope rearrangement, see: J. Chem. Soc., Chem. Commun., 381 (1995):
Strong base, for example Na bis(TMS)amide, brings about elimination of methanol, giving ketenylidenetriphenylphosphorane, which reacts with ɑ-hydroxy-ketones, e.g. in the steroid series, to give butenolides, by acylation and Wittig cyclization: Chem. Ber., 113, 2038 (1980):
Review of phosphacumulene ylides: Angew. Chem. Int. Ed., 16, 349 (1977).
Dierkes, G.; Bongartz, A.; Guth, H.; Hayen, H. Quality Evaluation of Olive Oil by Statistical Analysis of Multicomponent Stable Isotope Dilution Assay Data of Aroma Active Compounds. J. Agric. Food Chem., 2012, 60 (1), 394-401.
Mears, P. R.; Thomas, E. J. Difluoroallylation using a 2-bromomethyl-1,1-difluoroalk-1-ene. Tetrahedron Lett. 2015, 56 (26), 3980-3981.