| Identification | More | [Name]
BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE | [CAS]
88738-78-7 | [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%
Methyl p,p-bis(2,2,2trifluoroethyl)-phosphonoacetate, min. 90 %
(2-Methoxy-2-oxoethyl)phosphonic acid bis(2,2,2-trifluoroethyl) ester
(Methoxycarbonyl)methylphosphonic acid bis(2,2,2-trifluoroethyl) ester
[Bis(2,2,2-trifluoroethoxy)phosphinyl]acetic acid methyl ester | [Molecular Formula]
C7H9F6O5P | [MDL Number]
MFCD00009901 | [Molecular Weight]
318.11 | [MOL File]
88738-78-7.mol |
| Chemical Properties | Back Directory | [Appearance]
clear orange to dark orange-brown liquid | [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 | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [F ]
10 | [Hazard Note ]
Irritant | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [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.
| [Hazard]
Bis(2,2,2-trifluoroethyl) (Methoxycarbonylmethyl) phosphonate is irritant.
| [reaction suitability]
reaction type: C-C Bond Formation | [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. | [Purification Methods]
Silica gel chromatography.
|
| Spectrum Detail | Back Directory | [Spectrum Detail]
BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE(88738-78-7)MS
BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE(88738-78-7)1HNMR
BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE(88738-78-7)13CNMR
BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE(88738-78-7)IR1
BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE(88738-78-7)Raman
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