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410756

Sigma-Aldrich

Diethyl (2-oxo-2-phenylethyl)phosphonate

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

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.)

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

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

Eyeshields, Gloves

Certificates of Analysis (COA)

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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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