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374717

Sigma-Aldrich

Triethyl 2-fluoro-2-phosphonoacetate

96%

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:
2356-16-3
Molecular Weight:
242.18
Beilstein/REAXYS Number:
1912161
MDL number:
MFCD00134400
UNSPSC Code:
12352108
PubChem Substance ID:
24863330
NACRES:
NA.22

assay

96%

form

liquid

reaction suitability

reaction type: C-C Bond Formation

refractive index

n20/D 1.425 (lit.)

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

163.4 °F - closed cup

flash_point_c

73 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
08511KE
06209KD
28025CR
19829DA
18717BB

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P W Collins et al.
Journal of medicinal chemistry, 30(11), 1952-1955 (1987-11-01)
A 4-fluoro analogue of enisoprost was prepared and evaluated for gastric antisecretory and mucosal protective activity in animals. The synthesis centered upon cuprate chemistry but also involved a Wittig reaction to produce a cis fluoro olefinic moiety, a furan rearrangement/isomerization

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