3-(3-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER

3-(3-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER Property

Boiling point:

255-256 °C(lit.)

Density 

1.416 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.565(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

pka

9.91±0.46(Predicted)

Appearance

Light brown to reddish brown Liquid

CAS DataBase Reference

21575-91-7(CAS DataBase Reference)

Safety

WGK Germany 

3

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

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

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

P321Specific treatment (see … on this label).

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

P362Take off contaminated clothing and wash before reuse.

3-(3-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER Chemical Properties,Usage,Production

Uses

Reactant involved in synthesis of:

• Aroylbenzoxepinones for analgesic activity
• (Heteroaryl)(carboxamido)arylpyrrole derivatives with Cdc7 kinase inhibitory activity
• Cambinol analogs for sirtuin inhibition and antitumor activity
• TunePhos-type diphosphine ligands via asymmetric hydrogenation

Synthesis

A solution of 1.3 M LHMDS (25 mL, 32.7 mmol) in THF (10 mL) was stirred at -78 °C and under an inert atmosphere, and ethyl acetate (1.9 g, 21.8 mmol) was added slowly. After stirring for 15 min, ethyl 3-bromobenzoate (5 g, 21.8 mmol) was added and stirring was continued for 2 hours. The reaction progress was monitored by TLC. Upon completion of the reaction, the reaction was quenched with 10 mL of saturated aqueous NH4Cl and extracted with ethyl acetate (3 x 20 mL). The organic phases were combined, dried with anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography with 4% ethyl acetate/hexane as eluent to afford the target compound, ethyl 3-bromobenzoylacetate (4.5 g, 76.9%) as a mixture of enol forms in the form of a brown oil.1H NMR (500 MHz, CDCl3): δ 8.07 (s, 1H), 7.86 (d, J=7.5 Hz, 1H), 7.73 -7.69 (m, 1H), 7.37 (t, J=7.0Hz, 1H), 4.28-4.26 (m, 2H), 3.92 (s, 2H), 1.24 (t, J=6.2Hz, 3H).MS (ESI): m/z 298.8 [M-1].

References

[1] Patent: WO2015/191630, 2015, A1. Location in patent: Paragraph 00457
[2] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 13, p. 2991 - 3013