| Identification | More | [Name]
3-(4-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER | [CAS]
26510-95-2 | [Synonyms]
3-(4-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER
ETHYL 3-(4-BROMOPHENYL)-3-OXOPROPANOATE
ETHYL (4-BROMOBENZOYL)ACETATE
3-(4-Bromophenyl)-3-oxo-propionic acid | [Molecular Formula]
C11H11BrO3 | [MDL Number]
MFCD00231243 | [Molecular Weight]
271.11 | [MOL File]
26510-95-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear yellow to light brown liquid | [Boiling point ]
268-269 °C(lit.) | [density ]
1.432 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.5700(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
Liquid | [pka]
9.56±0.25(Predicted) | [color ]
Clear yellow | [InChI]
1S/C11H11BrO3/c1-2-15-11(14)7-10(13)8-3-5-9(12)6-4-8/h3-6H,2,7H2,1H3 | [InChIKey]
PBDYXCKRDRCJDC-UHFFFAOYSA-N | [SMILES]
CCOC(=O)CC(=O)c1ccc(Br)cc1 | [CAS DataBase Reference]
26510-95-2(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Clear yellow to light brown liquid | [Uses]
Ethyl (4-bromobenzoyl)acetate may be used to synthesize 2-(carboethoxy)-3-(4′-bromo)phenylquinoxaline 1,4-dioxide. | [Uses]
Ethyl 3-(4-bromophenyl)-3-oxo-propionate | [General Description]
Ethyl (4-bromobenzoyl)acetate can be prepared by employing the following reagents:
- ethyl acetylacetate
- petroleum ether
- NaOH
- 4-bromobenzoyl chloride
| [Synthesis]
Diethyl carbonate (295 g, 2.50 mol) was slowly added to a suspension of NaH (80 g, 60% mineral oil dispersion, 2 mol) in toluene (1.2 L) at 0 °C. After stirring at room temperature for 2 h, the mixture was slowly added dropwise under reflux conditions to a solution of p-bromoacetophenone (99 g, 0.50 mol) in toluene (400 mL). After the reaction mixture was refluxed overnight, it was cooled to room temperature and quenched sequentially with acetic acid (140 mL) and 2M aqueous hydrochloric acid (864 mL). The resulting mixture was extracted with ethyl acetate (400 mL x 3), the organic phases were combined, washed sequentially with water (500 mL x 4) and saturated saline (200 mL x 2) and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure and the residue was dried under vacuum to give ethyl (4-bromobenzoyl)acetate (122 g, 90% yield) as an oil.LC-MS (ESI): m/z 271.0 [M + H]+. | [References]
[1] European Journal of Organic Chemistry, 2017, vol. 2017, # 31, p. 4543 - 4547
[2] Patent: WO2012/58125, 2012, A1. Location in patent: Page/Page column 147
[3] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 1950 - 1956
[4] Archiv der Pharmazie, 2003, vol. 336, # 3, p. 181 - 190
[5] Molecules, 2004, vol. 9, # 3, p. 135 - 157 |
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