BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE Property

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

10

Hazard Note 

Irritant

HS Code 

29319090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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

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.