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| | BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE Basic information |
| Product Name: | BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE | | Synonyms: | BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE;BIS(2,2,2-TRIFLUOROETHYL)PHOSPHONOACETIC ACID METHYL ESTER;METHYL [BIS(2,2,2-TRIFLUOROETHOXY)PHOSPHINYL]ACETATE;METHYL BIS(2,2,2-TRIFLUOROETHYL)PHOSPHONOACETATE;METHYL O,O'-BIS(2,2,2-TRIFLUOROETHYL)PHOSPHONOACETATE;METHYL P,P-BIS(2,2,2-TRIFLUOROETHYL)PHOSPHONOACETATE;Bis(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate 95%;Bis(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate95% | | CAS: | 88738-78-7 | | MF: | C7H9F6O5P | | MW: | 318.11 | | EINECS: | | | Product Categories: | Small molecule;Horner-Emmons Reaction;Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction | | Mol File: | 88738-78-7.mol |  |
| | 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.) | | Fp | >230 °F | | storage temp. | Inert atmosphere,Room Temperature | | form | Liquid | | color | Clear orange to dark orange-brown | | Specific Gravity | 1.50 | | BRN | 3594044 | | InChIKey | PVSJXEDBEXYLML-UHFFFAOYSA-N | | CAS DataBase Reference | 88738-78-7(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | F | 10 | | Hazard Note | Irritant | | HS Code | 29319090 |
| | 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 Preparation Products And Raw materials |
| Raw materials | methylacetylphosphonate-->Acetic acid, 2-[bis[(trimethylsilyl)oxy]phosphinyl]-, methyl ester-->Acetic acid, 2-(dichlorophosphinyl)-, methyl ester-->2,2,2-Trifluoroethanol | | Preparation Products | (2E,4E,6Z)-methyl deca-2,4,6-trienoate-->Propanoic acid, 2-[bis(2,2,2-trifluoroethoxy)phosphinyl]-, methyl ester |
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