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Safety Information

47400

Sigma-Aldrich

Triethyl 2-fluoro-2-phosphonoacetate

technical, ≥96% (GC)

Synonym(s):

2-Fluoro-2-phosphonoacetic acid triethyl ester, Diethyl [(ethoxycarbonyl)fluoromethyl]phosphonate, Ethyl diethylphosphonofluoroacetate

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About This Item

Linear Formula:
(C2H5O)2P(O)CH(F)CO2C2H5
CAS Number:
Molecular Weight:
242.18
Beilstein:
1912161
MDL number:
UNSPSC Code:
12352000

grade

technical

Assay

≥96% (GC)

refractive index

n20/D 1.425 (lit.)
n20/D 1.625

bp

75 °C/0.01 mmHg (lit.)

density

1.194 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)C(F)P(=O)(OCC)OCC

InChI

1S/C8H16FO5P/c1-4-12-8(10)7(9)15(11,13-5-2)14-6-3/h7H,4-6H2,1-3H3

InChI key

FVPISMANESAJQZ-UHFFFAOYSA-N

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Application

Reactant for:
  • Diels-Alder reactions
  • Biosynthesis of terpene
  • Stereoselective synthesis of unsaturated esters, fluorides and nitriles from the reactions of aldehydes and ketones using Wadsworth-Emmons phosphonates
  • Synthesis of quinolones
  • Horner-Wadsworth-Emmons asymmetric hydration
  • Addition reactions and the subsequent application to click chemistry
  • Asymmetric intermolecular Stetter reactions

Other Notes

Horner-Wittig reagent for the synthesis of α-fluoro-α,β-unsaturated esters

replaced by

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A. Thenappan et al.
The Journal of Organic Chemistry, 55, 4639-4639 (1990)
G. Etemad-Moghadam et al.
Bulletin de la Societe Chimique De France, 448-448 (1985)
H.J. Tsai et al.
The Journal of Organic Chemistry, 59, 7085-7085 (1994)

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