Ethyl 4-bromoacetoacetate Chemical Properties

Boiling point:

231.6 °C

Density 

1.511

refractive index 

1.5281 (estimate)

storage temp. 

2-8°C(protect from light)

pka

9.56±0.46(Predicted)

form 

liquid

color 

Colourless

InChI

InChI=1S/C6H9BrO3/c1-2-10-6(9)3-5(8)4-7/h2-4H2,1H3

InChIKey

MGDWUTQKXCZNAJ-UHFFFAOYSA-N

SMILES

C(OCC)(=O)CC(=O)CBr

Safety Information

Hazard Codes 

F

HS Code 

2918300090

Ethyl 4-bromoacetoacetate Usage And Synthesis

Chemical Properties

Density 1.511 (28℃) 1.528 (18℃), boiling point 115-116℃/15mmHg.

Synthesis

To a solution of Ethyl acetoacetate (10.0 g, 76.9 mmol, 1 .0 eq) in acetic acid (30 mL) was added bromine (12.3 g, 76.9 mmol, 1 .0 eq) at 0 °C over 10 min. The mixture was stirred at 0 °C for 1 h, the solvent was removed under reduced pressure, and the residue was diluted with water (50 mL). The aqueous mixture was extracted with CH2CI2 (50 mL x 3). The combined organic layers were washed with brine (60 mL x 2), dried over MgS04 and concentrated under reduced pressure to give ethyl 4-bromo-3-oxobutanoate (14.3 g, 85 per cent) as a yellow oil.

References

[1] Patent: CN105820102, 2016, A. Location in patent: Paragraph 0029-0031
[2] Patent: WO2012/63085, 2012, A2. Location in patent: Page/Page column 81
[3] Patent: US2013/225594, 2013, A1. Location in patent: Paragraph 0252; 0253
[4] Canadian Journal of Chemistry, 2001, vol. 79, # 8, p. 1259 - 1271
[5] Patent: TW2016/5831, 2016, A. Location in patent: Paragraph 0211

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