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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 | Philadelphia, PA | Portland, OR | Japan* | Quantity |
Shipping Information
|
|---|---|---|---|---|---|---|
| 1G |
$51.00
|
Ships from Portland the same day* | 1 | 7 |
|
|
| 5G |
$174.00
|
1 | Ships from Philadelphia the same day* | 23 |
|
|
| 25G |
$678.00
|
2 | 1 | 14 |
|
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| 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. P337 + P313 : If eye irritation persists: Get medical advice/ attention. P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P302 + P352 : IF ON SKIN: Wash with plenty of soap and water. P332 + P313 : If skin irritation occurs: Get medical advice/ attention. P362 : Take off contaminated clothing and wash before reuse. |
Related Laws:
Transport Information:
| HS Number | 2931.59.0080 |
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.
PubMed Literature
Documents
Product Articles
[TCI Practical Example] Z-Stereoselective Horner-Wadsworth-Emmons Olefination via Still-Gennari MethodProduct Documents (Note: Some products will not have analytical charts available.)
Safety Data Sheet (SDS)
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Specifications
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