ethyl 4-cyclopropyl-2,4-dioxobutanoate

ethyl 4-cyclopropyl-2,4-dioxobutanoate Property

Boiling point:

149 °C(Press: 23 Torr)

Density 

1.218±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

6.79±0.20(Predicted)

Appearance

Colorless to light yellow Liquid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

ethyl 4-cyclopropyl-2,4-dioxobutanoate Chemical Properties,Usage,Production

Synthesis

Sodium ethanolate solution was prepared by dissolving sodium metal (16.19 g) in anhydrous ethanol (150 ml) at room temperature and under nitrogen protection. After cooling the reaction mixture to 0°C, a mixture of diethyl oxalate (34.76 g) and cyclopropylmethyl ketone (20 g) was slowly added dropwise for about 15 min. After the dropwise addition was completed, the reaction mixture was allowed to warm up to room temperature naturally. Subsequently, anhydrous ethanol (100 ml) was added and stirring was continued for 1 hour at room temperature. The reaction mixture was heated to 80 °C, maintained for 45 minutes and then cooled to room temperature and subsequently concentrated under reduced pressure. Ethyl acetate was added to the resulting solid, washed with ethanol and filtered through a Brinell funnel to give a fine powdery solid. The solid was dissolved in water and acidified by adjusting the pH to 2 with dilute sulfuric acid. The acidified solution was extracted with ether, the organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure to obtain the target compound ethyl 4-cyclopropyl-2,4-oxobutanoate in brown liquid form (40 g, 93% yield).

References

[1] Patent: WO2010/127855, 2010, A1. Location in patent: Page/Page column 159
[2] Patent: US2012/115903, 2012, A1. Location in patent: Page/Page column 40
[3] Patent: WO2012/62463, 2012, A1. Location in patent: Page/Page column 87-88
[4] Patent: WO2013/39988, 2013, A1. Location in patent: Page/Page column 138
[5] Patent: US2003/236287, 2003, A1. Location in patent: Page 46, 47