BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE
Synonym(s):Bis(2,2,2-trifluoroethyl) (methoxycarbonylmethyl)phosphonate
- CAS NO.:88738-78-7
- Empirical Formula: C7H9F6O5P
- Molecular Weight: 318.11
- MDL number: MFCD00009901
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-08-15 16:23:59
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 | n |
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) |
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 |
New Products
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