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HomeProduct name listBIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE

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

Synonym(s):Bis(2,2,2-trifluoroethyl) (methoxycarbonylmethyl)phosphonate

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

What is BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE?

Chemical properties

clear orange to dark orange-brown liquid

The Uses of BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE

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.

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

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
color  Clear orange to dark orange-brown
Specific Gravity 1.50
BRN  3594044
CAS DataBase Reference 88738-78-7(CAS DataBase Reference)

Safety information for BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE

InChIKey PVSJXEDBEXYLML-UHFFFAOYSA-N

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