Diethyl (2-oxo-2-phenylethyl)phosphonate

Name: Diethyl (2-oxo-2-phenylethyl)phosphonate
Brand: ALDRICH
Price: 67.65 USD
Availability: InStock

97%

Synonym(s):

Diethyl benzoylmethylphosphonate, Diethyl phenacylphosphonate, NSC 648426

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About This Item

Linear Formula:

C₆H₅COCH₂P(O)(OC₂H₅)₂

CAS Number:

3453-00-7

Molecular Weight:

256.23

MDL number:

MFCD00015342

UNSPSC Code:

12352108

PubChem Substance ID:

24865704

NACRES:

NA.22

Key Documents

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assay

97%

reaction suitability

reaction type: C-C Bond Formation

refractive index

n20/D 1.513 (lit.)

bp

192-193 °C/11 mmHg (lit.)

density

1.179 g/mL at 25 °C (lit.)

functional group

ketone
phenyl
phosphonate

SMILES string

CCOP(=O)(CC(=O)c1ccccc1)OCC

InChI

1S/C12H17O4P/c1-3-15-17(14,16-4-2)10-12(13)11-8-6-5-7-9-11/h5-9H,3-4,10H2,1-2H3

InChI key

HPEVTTNSIPGLEL-UHFFFAOYSA-N

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This Item	D99250	408573	D91152
Sigma-Aldrich 410756 Diethyl (2-oxo-2-phenylethyl)phosphonate	Sigma-Aldrich D99250 Diethyl 2,2-diethoxyethylphosphonate	Sigma-Aldrich 408573 Diethyl (1-cyanoethyl)phosphonate	Sigma-Aldrich D91152 Diethyl 2-bromoethylphosphonate
assay 97%	assay 95%	assay 97%	assay 97%
reaction suitability reaction type: C-C Bond Formation	reaction suitability reaction type: C-C Bond Formation	reaction suitability reaction type: C-C Bond Formation	reaction suitability reaction type: C-C Bond Formation
bp 192-193 °C/11 mmHg (lit.)	bp 146-149 °C/14 mmHg (lit.)	bp 140-141 °C/11 mmHg (lit.)	bp 75 °C/1 mmHg (lit.)
density 1.179 g/mL at 25 °C (lit.)	density 1.052 g/mL at 25 °C (lit.)	density 1.085 g/mL at 25 °C (lit.)	density 1.348 g/mL at 25 °C (lit.)
refractive index n20/D 1.513 (lit.)	refractive index n20/D 1.430 (lit.)	refractive index n20/D 1.432 (lit.)	refractive index n20/D 1.461 (lit.)
functional group ketone	functional group -	functional group nitrile, phosphonate	functional group -

Application

Reactant involved in:

Asymmetric Michael addition of β-oxo phosphonates to nitro olefins
Gem-chlorofluorination of keto phosphonates with subsequent functionalization of the products
Cyclocondensation reactions to produce arylphosphonates
Diazo transfer reactions for synthesis of diazo-phosphonyl compounds
Horner-Wadsworth-Emmons reactions
Inverse-electron-demand Diels-Alder reactions

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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A Convenient Reagent for Aldehyde to Alkyne Homologation.

Douglass F Taber et al.

Tetrahedron letters, 49(48), 6904-6906 (2009-12-01)

An convenient reagent for the one-carbon homologation of an aldehyde to the corresponding alkyne is reported. This reagent allows this conversion to conveniently be carried out on a large scale under ambient conditions.

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Diethyl (2-oxo-2-phenylethyl)phosphonate