Triethyl 2-fluoro-2-phosphonoacetate Chemical Properties

Boiling point:

75 °C0.01 mm Hg(lit.)

Density 

1.194 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.425(lit.)

Flash point:

165 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

clear liquid

color 

Colorless to Almost colorless

Specific Gravity

1.194

BRN 

1912161

InChI

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

InChIKey

FVPISMANESAJQZ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

2356-16-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,F

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

F 

10-21

Hazard Note 

Irritant

HazardClass 

IRRITANT, FLAMMABLE

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Triethyl 2-fluoro-2-phosphonoacetate Usage And Synthesis

Chemical Properties

clear colorless liquid

Uses

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

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 4730, 1995 DOI: 10.1021/jo00120a014

reaction suitability

reaction type: C-C Bond Formation

Synthesis

Ethyl 2-bromo-2-fluoroacetate (5.0 g, 27 mmol) was mixed with triethyl phosphite (13 mL) and the reaction was heated at 130°C for 23 hours. After completion of the reaction, the resulting mixture was distilled under reduced pressure (1.4 mbar, 75-110°C) to afford triethyl 2-fluoro-2-phosphonoacetate, the product being a pale yellow oil (6.0 g, 92% yield).

References

[1] Phosphorus, Sulfur and Silicon and Related Elements, 2000, vol. 160, p. 195 - 205
[2] Patent: WO2017/100668, 2017, A1. Location in patent: Page/Page column 162
[3] Patent: WO2018/103058, 2018, A1. Location in patent: Page/Page column 161; 165-166; 339
[4] Journal of the American Chemical Society, 2007, vol. 129, # 15, p. 4536 - 4537
[5] Heterocycles, 2004, vol. 63, # 3, p. 699 - 706

Triethyl 2-fluoro-2-phosphonoacetate(2356-16-3)Related Product Information

• Ethyl chloroacetate
• Ethyl bromodifluoroacetate
• Ethyl acetate
• Ethyl trifluoroacetate
• Triethyl phosphate
• Triethyl phosphite
• Ethyl phenylacetate
• Triethyl phosphonoacetate
• Ethyl bromoacetate
• Triethyl 2-chloro-2-phosphonoacetate
• Ethyl dimethylphosphonoacetate
• Ethyl fluoroacetate
• DIETHYLPHOSPHONOACETIC ACID
• Trimethyl phosphonoacetate
• PHOSPHONOACETIC ACID
• Methyl diethylphosphonoacetate
• TRIETHYL PHOSPHONOACETATE
• ARSENIC ACID TRIETHYL ESTER