BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE Chemical Properties

Boiling point:

246.6±40.0 °C(Predicted)

Density 

1.504 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.370(lit.)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,Room Temperature

form 

Liquid

Specific Gravity

1.50

color 

Clear orange to dark orange-brown

BRN 

3594044

InChI

InChI=1S/C7H9F6O5P/c1-16-5(14)2-19(15,17-3-6(8,9)10)18-4-7(11,12)13/h2-4H2,1H3

InChIKey

PVSJXEDBEXYLML-UHFFFAOYSA-N

SMILES

C(OC)(=O)CP(OCC(F)(F)F)(OCC(F)(F)F)=O

CAS DataBase Reference

88738-78-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

10

Hazard Note 

Irritant

HS Code 

29319090

MSDS

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

BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE Usage And Synthesis

Chemical Properties

clear orange to dark orange-brown liquid

Uses

Methyl?P,P-bis(2,2,2-trifluoroethyl)phosphonoacetate can be used:

• In one of the key synthetic steps for the preparation of?trans-hydrindanes and (R)-(+)-umbelactone.
• To prepare a cis-olefinic ester derivative by Still–Gennari olefination of an aldehyde derivative using 18-crown ether and potassium bis(trimethylsilyl)amide (KHMDS).
• In the synthesis of (?)-(6S,2′S)-epi?cryptocaryalactone.

Synthesis

The synthesis method of Bis(2,2,2-trifluoroethyl) (Methoxycarbonylmethyl) phosphonate is as follows: To a stirred solution of dried 18-crown-6 (4.53 g, 17.14 mmol), THF (20 mL), and Bis(2,2,2-trifluoroethyl) Phosphite (0.70 mL, 1.29 mmol), was added KHMDS (9.0 mL, 4.50 mmol, 0.5M in toluene) by syringe in a dropwise manner at -78 ℃. After 15 min, methyl chloroacetate (0.30 mL, 3.41 mmol) was added and the reaction mixture was allowed to stir for 4 hr at room temperature. The reaction mixture was diluted with EtOAc (20 mL) and then quenched with sat. ammonium chloride (50 mL). The aqueous layer was extracted with EtOAc (3 x 30 mL). The combined organic extracts were dried under anhydrous magnesium sulfate. Following filtration, the solvents were removed in vacuo. The crude product was then purified by flash column chromatography (33% EtOAc in hexanes, Rf = 0.22 in 33% EtOAc in hexanes) yielding Bis(2,2,2-trifluoroethyl) (Methoxycarbonylmethyl)phosphonate (766 mg, 2.41 mmol, 70.3%) as a yellow syrup.

BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE(88738-78-7)Related Product Information

• TFEC
• MALONIC ACID BIS(2,4,6-TRICHLOROPHENYL) ESTER
• BIS(2,2,2-TRIFLUOROETHYL) PHOSPHITE
• Dimethyl 2-hydroxyethylphosphonate
• PHOSPHONOACETIC ACID
• DIETHYL ETHYLPHOSPHONATE
• DIMETHYL ETHYLPHOSPHONITE
• DIETHYLPHOSPHONOACETIC ACID
• Trimethyl phosphonoacetate
• DIMETHYL ETHYLPHOSPHONATE
• Methyl diethylphosphonoacetate
• Diethyl methylphosphonate
• Methyldiethoxyphosphine
• ETHYL METHYLPHOSPHONIC ACID
• BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE
• METHYLPHOSPHONIC ACID
• ETHYLPHOSPHONIC ACID
• 2,2,2-TRIFLUOROETHYL TRICHLOROMETHANESULFONATE