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Published TCIMAIL newest issue No.197
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CAS RN: 88738-78-7 | Product Number: B1714
Bis(2,2,2-trifluoroethyl) (Methoxycarbonylmethyl)phosphonate
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Purity: >95.0%(GC)
Synonyms:
- Bis(2,2,2-trifluoroethyl)phosphonoacetic Acid Methyl Ester
- Methyl [Bis(2,2,2-trifluoroethoxy)phosphinyl]acetate
- Methyl Bis(2,2,2-trifluoroethyl)phosphonoacetate
Product Documents:
| Size | Unit Price | Belgium | Japan* | Quantity |
|---|---|---|---|---|
| 1G |
£41.00
|
1 | 6 |
|
| 5G |
£131.00
|
Contact Us | 30 |
|
| 25G |
£512.00
|
3 | 2 |
|
*Stock available in Belgium will be delivered in 1 to 3 days
*Stock available in Japan will be delivered in 1 to 2 weeks (excludes regulated items and dry ice shipments).
| Product Number | B1714 |
| Purity / Analysis Method | >95.0%(GC) |
| Molecular Formula / Molecular Weight | C__7H__9F__6O__5P = 318.11 |
| Physical State (20 deg.C) | Liquid |
| Storage Temperature | Room Temperature (Recommended in a cool and dark place, <15°C) |
| Store Under Inert Gas | Store under inert gas |
| Condition to Avoid | Air Sensitive |
| CAS RN | 88738-78-7 |
| Reaxys Registry Number | 3594044 |
| PubChem Substance ID | 87564613 |
| SDBS (AIST Spectral DB) | 21981 |
| MDL Number | MFCD00009901 |
Specifications
| Appearance | Colorless to Light yellow clear liquid |
| Purity(GC) | min. 95.0 % |
Properties (reference)
| Specific Gravity (20/20) | 1.50 |
| Refractive Index | 1.37 |
GHS
| Pictogram |
|
| Signal Word | Warning |
| Hazard Statements | H315 : Causes skin irritation. H319 : Causes serious eye irritation. |
| Precautionary Statements | P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ eye protection/ face protection. P302 + P352 : IF ON SKIN: Wash with plenty of water. P337 + P313 : If eye irritation persists: Get medical advice/ attention. P362 + P364 : Take off contaminated clothing and wash it before reuse. P332 + P313 : If skin irritation occurs: Get medical advice/ attention. |
Related Laws:
Transport Information:
| HS Number | 2931599090 |
Application
TCI Practical Example: Z-Stereoselective Horner-Wadsworth-Emmons Olefination via Still-Gennari Method
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Used Chemicals
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Procedure
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Potassium tert-butoxide (236 mg, 2.1 mmol, 2.1 eq.) in dry THF (5 mL) was added dropwise to the solution of p-tolualdehyde (120 mg, 1.0 mmol), bis(2,2,2-trifluoroethyl) (methoxycarbonylmethyl)phosphonate (636 mg, 2.0 mmol, 2.0 eq.) and 18-crown-6-ether (793 mg, 3.0 mmol, 3.0 eq.) in dry THF (5 mL) at -78 °C. The mixture was stirred for 2 hours. Then the mixture was stirred at r.t. for overnight and quenched with water (15 mL). The aqueous layer was extracted with ethyl acetate (15 mL x 3) and the combined organic layer was washed with 2 mol/L HCl aq. (10 mL), sat. NaHCO3 aq. (10 mL), and brine (10 mL), dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography (on silica gel, toluene:diethyl ether = 40:1) to give 1 as a pale yellow liquid (138 mg, 78% yield, E:Z = 1:15.5).
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Experimenter’s Comments
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The reaction mixture was monitored by UPLC.
The ratio of E form and Z form was estimated from NMR.
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Analytical Data
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Compound 1
1H NMR (400 MHz, CDCl3);
1-Z: δ 7.53 (d, J = 7.6 Hz, 2H), 7.17 (d, J = 7.6 Hz, 2H), 6.91 (d, J = 12.8 Hz, 1H), 5.90 (d, J = 12.8 Hz, 1H), 3.72 (s, 3H), 2.36 (s, 3H).
1-E: δ 7.67 (d, J = 16.0 Hz, 1H), 7.42 (d, J = 8.4 Hz, 2H), 7.20 (d, J = 8.4 Hz, 2H), 6.40 (d, J = 16.0 Hz, 1H), 3.80 (s, 3H), 2.37 (s, 3H). -
Lead Reference
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- Direct synthesis of Z-unsaturated esters. A useful modification of the horner-emmons olefination.
Application
Z-Selective Horner-Emmons Olefination
References
Direct synthesis of Z-unsaturated esters
S. J. Danishefsky, M. P. DeNinno, J. Org. Chem. 1986, 51, 2615.
W. R. Roush, A. D. Palkowitz, ibid. 1989, 54, 3009.
α-Alkylation of reagent B1714 and olefination
J. C. Medina, R. Guajardo, K. S. Kyler, J. Am. Chem. Soc. 1989, 111, 2310.
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