4-Bromo-6-chloro-indan-1-one

4-Bromo-6-chloro-indan-1-one Property

storage temp. 

Sealed in dry,Room Temperature

Appearance

Off-white to light brown Solid

InChI

InChI=1S/C9H6BrClO/c10-8-4-5(11)3-7-6(8)1-2-9(7)12/h3-4H,1-2H2

InChIKey

WCCKBUGGMIUBNX-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C(Br)=CC(Cl)=C2)CC1

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

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

4-Bromo-6-chloro-indan-1-one Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 4-bromo-6-chloro-2,3-dihydro-1H-inden-1-one using 3-(2-bromo-4-chlorophenyl)propionic acid as starting material was as follows: oxalyl chloride (3.6 mL) was added slowly and dropwise under stirring to a solution of 3-(2-bromo-4-chlorophenyl)propionic acid (4.4 g) in dichloromethane (40 mL). The reaction mixture was stirred continuously at 40 °C for 2 hours. Subsequently, aluminum trichloride (AlCl3, 2.7 g) was added to the reaction system and the mixture was heated to reflux and maintained for 1 hour. Upon completion of the reaction, the mixture was cooled to room temperature and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate (NaHCO3). The aqueous phase was extracted twice with ethyl acetate, all organic phases were combined and washed with brine. The organic layer was dried over anhydrous sodium sulfate (Na2SO4) and evaporated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography with the eluent cyclohexane/ethyl acetate (95:5→90:10) to afford the target compound 4-bromo-6-chloro-2,3-dihydro-1H-inden-1-one. Yield: 3.7 g; liquid chromatography (Method 1): retention time (tR) = 1.20 min; mass spectrometry (ESI+): m/z = 245 [M + H]+.

References

[1] Patent: WO2013/144098, 2013, A1. Location in patent: Page/Page column 123
[2] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 16, p. 3368 - 3372