Dimethyl fluoromalonate CAS#: 344-14-9; 凯望编码 (ChemWhat Code): 55481
Identification
| 英文名 | Dimethyl fluoromalonate |
| IUPAC Name | dimethyl 2-fluoropropanedioate |
| 分子结构 |  |
| CAS编号 | 344-14-9 |
| MDL Number | MFCD00054680 |
| 别名 | dimethyl 2-fluoromalonate DIMETHYL FLUOROMALONATE 344-14-9 dimethylfluoromalonate dimethyl2-fluoromalonate |
| 分子式 | C5H7FO4 |
| 分子量 | 150.107 |
| InChI | InChI=1S/C5H7FO4/c1-9-4(7)3(6)5(8)10-2/h3H,1-2H3 |
| InChI Key | ZVXHZSXYHFBIEW-UHFFFAOYSA-N |
| Canonical SMILES | COC(=O)C(C(=O)OC)F |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| US5319131 | α-fluoroacrylic acid esters and polymers thereof | 1994 |
| EP249867 | Substituted phenyl esters of alpha-fluoroacrylic acid | 1987 |
Physical Data
| Appearance | Colorless to yellow liquid or solid (low temperature) |
| Boiling Point, °C | Pressure (Boiling Point), Torr |
| 111-112 | 45 |
| 76 | 4 |
| 82-85 | 15 |
| 100 – 102 | 22 |
| Refractive Index | Wavelength (Refractive Index), nm | Temperature (Refractive Index), °C |
| 1.4008 | 589 | 20 |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Temperature (NMR Spectroscopy), °C | Frequency (NMR Spectroscopy), MHz |
| Chemical shifts, Spectrum | 1H | chloroform-d1 | 25 | 400 |
| Chemical shifts, Spectrum | 13C | chloroform-d1 | 25 | 101 |
| Chemical shifts, Spectrum | 19F | chloroform-d1 | 25 | 376 |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) | Comment (IR Spectroscopy) |
| Bands | neat (no solvent) | 1750 cm**(-1) |
Route of Synthesis (ROS)
| Conditions | Yield |
| With copper nitrate hemi(pentahydrate); fluorine In acetonitrile at 0 – 5℃; for 7h; Green chemistry; | 97% |
| With sodium hydride; N-fluorobis<(trifluoromethyl)sulfonyl>imide In tetrahydrofuran at -50 – 22℃; for 5h; | 78% |
| With triethylamine pentahydrogen fluoride salt; iodosylbenzene In 1,2-dichloro-ethane at 70℃; for 24h; Experimental Procedure Fluorination of Malonic Esters 1; General Procedure General procedure: PhIO (550 mg, 2.5 mmol), Et3N·5HF (800 mg, 4 mmol), and DCE (1 mL)were placed in a Teflon test tube. After stirring at r.t. for 15 min, the appropriate malonic ester 1 (1 mmol) and DCE (1 mL) were added. The test tube was sealed with a septum rubber and heated at 70 °C for 24 h with stirring. The reaction mixture was neutralized with aq NaHCO3 and the product was extracted with CH2Cl2 (3 × 10 mL). The combined organic layers were washed with brine (20 mL), dried (Na2SO4), and concentrated under reduced pressure. The product was purified by column chromatography on silica gel with hexane–CH2Cl2 as eluent. | 45% |
| With uranium hexafluoride In 1,1,2-Trichloro-1,2,2-trifluoroethane at 20℃; for 20h; Inert atmosphere; | 15% |
| With N-fluorobis<(trifluoromethyl)sulfonyl>imide 1.) THF, 2.) 5 h; Yield given. Multistep reaction; |
Safety and Hazards
| Pictogram(s) |   |
| Signal | Danger |
| GHS Hazard Statements | H301: Toxic if swallowed [Danger Acute toxicity, oral] H311: Toxic in contact with skin [Danger Acute toxicity, dermal] H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation] H331: Toxic if inhaled [Danger Acute toxicity, inhalation] Information may vary between notifications depending on impurities, additives, and other factors. |
| Precautionary Statement Codes | P260, P261, P264, P270, P271, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P330, P361, P363, P403+P233, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Other Data
| Transportation | Class 8; Packaging Group: II; UN Number: 3265 |
| Under the room temperature and away from light | |
| HS Code | 294200 |
| Storage | Under the room temperature and away from light |
| Shelf Life | 1 year |
| Market Price | USD 45/kg |
| Use Pattern |
| Dimethyl fluoromalonate CAS#: 344-14-9 is an intermediate product for production of 4,6-dichloro-5-flouoro-pyrimidine. |
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