Dimethyl fluoromalonate Chemical Properties

Boiling point:

76 °C

Density 

1.4g/ml

refractive index 

1.4032

Flash point:

111-112°C/45mm

pka

10.35±0.46(Predicted)

form 

solid

color 

Colourless to off-white / liquid

BRN 

1768414

CAS DataBase Reference

344-14-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,C

Risk Statements 

34

Safety Statements 

26-36/37/39-45-23 2636/37/3945-20

RIDADR 

3265

Hazard Note 

Toxic

HazardClass 

8

PackingGroup 

II

HS Code 

29171900

MSDS

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Dimethyl fluoromalonate Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

Dimethyl 2-fluoromalonate is used as an intermediate in organic synthesis.

Preparation

synthesis of dimethyl 2-fluoromalonate: Dimethyl malonate (19.8 g, 0.15 mol) and Cu(NO3)2·2.5H2O (3.50 g, 15 mmol) were dissolved in acetonitrile (85 mL), the mixture was cooled to 0–5 °C and stirred at 650 rpm using an overhead stirrer. After purging the system with N2 for 5 minutes, fluorine gas (20% v/v in N2, 50 mL min-1 , 170 mmol) was introduced into the reaction mixture for 7 h. After purging with nitrogen for 20 minutes, the solvent was removed in vacuo and the residue was partitioned between water (30 mL) and ethyl acetate (20 mL). The aqueous phase was extracted with ethyl acetate (2 × 20 mL) and the combined organic layer was washed with saturated brine (20 mL). After drying over sodium sulphate, the solvent was evaporated under reduced pressure to give dimethyl 2-fluoromalonate (21.8 g, 97% yield, 95% purity) as a colourless oil;
IR (neat, cm-1 ) 2962, 1748, 1438, 1250, 1206, 1112, 1016; δH (CDCl3, 400 MHz) 3.85 (6H, s, CH3), 5.31 (1H, d, 2 JHF 48.0, CHF); δF (CDCl3, 376 MHz): -195.73 (d, 2 JHF 48.0, CH–F); δC (CDCl3, 100 MHz) 53.48 (CH3), 85.19 (d, 1 JCF 197.2, C–F), 164.39 (d, 2 JCF 24.0, CvO); m/z (EI+ ) 150 (3%, [M]+ ), 119 (42%, [M-OMe]+ ), 91 (73%, [M-COOMe]+ ), 59 (100%, [COOMe]+ ).

Dimethyl fluoromalonate(344-14-9)Related Product Information

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