DIETHYL 2-FLUORO-2-METHYL-MALONATE Chemical Properties

Boiling point:

74-75°C 7mm

Density 

1?+-.0.06 g/cm3(Predicted)

storage temp. 

2-8°C

Appearance

Colorless to light yellow Liquid

Safety Information

Risk Statements 

34-36/37/38

Safety Statements 

26-36/37/39

RIDADR 

1760

DIETHYL 2-FLUORO-2-METHYL-MALONATE Usage And Synthesis

Synthesis Reference(s)

Journal of the American Chemical Society, 109, p. 7194, 1987 DOI: 10.1021/ja00257a051

Synthesis

In a test tube fitted with a stir bar, N-fluorobis(methylsulfonyl)imide (38.2 mg, 0.2 mmol) and 1,2-dichloroethane (1.0 mL) were added and stirred at room temperature until completely dissolved. Subsequently, diethyl 2-methylmalonate (17.4 mg, 0.1 mmol) and tetraisopropoxy prototitanate (0.016 mL, 0.05 mmol) were added to this solution and the reaction was carried out for 12 hours at room temperature. After completion of the reaction, water was added, extracted with dichloromethane (3 times), the organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to give the crude product. The crude product was analyzed by 19F-NMR and the yield of the target product diethyl 2-fluoro-2-methylmalonate was quantified using hexafluorobenzene as an internal standard. Finally, the product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane = 10/90, v/v) to afford the purified diethyl 2-fluoro-2-methylmalonate (7) as a colorless and transparent liquid (18.7 mg, 0.097 mmol, 97% yield).

References

[1] Patent: JP2016/23178, 2016, A. Location in patent: Paragraph 0031-0033
[2] Green Chemistry, 2016, vol. 18, # 7, p. 1864 - 1868
[3] Patent: WO2017/49069, 2017, A1. Location in patent: Paragraph 00160
[4] Journal of the American Chemical Society, 1984, vol. 106, # 2, p. 452 - 454
[5] Canadian Journal of Chemistry, 1965, vol. 43, p. 1700 - 1713

DIETHYL 2-FLUORO-2-METHYL-MALONATE(16519-02-1)Related Product Information

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• DIETHYL 2-FLUORO-2-METHYL-MALONATE
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• Diethyl fluoromalonate
• 2-FLUORO-2-METHANESULFONYLOXYMETHYL-MALONIC ACID DIETHYL ESTER
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