2-Bromo-3',4'-(methylenedioxy)propiophenone Chemical Properties

Boiling point:

345.7±42.0 °C(Predicted)

Density 

1.584±0.06 g/cm3(Predicted)

solubility 

Chloroform: Soluble; DMSO: 1 mg/mL*; Ethanol: 1 mg/mL

form 

A crystalline solid

InChI

InChI=1S/C10H9BrO3/c1-6(11)10(12)7-2-3-8-9(4-7)14-5-13-8/h2-4,6H,5H2,1H3

InChIKey

NTPQGLLTGPTOAA-UHFFFAOYSA-N

SMILES

C(C1=CC=C2OCOC2=C1)(=O)C(Br)C

2-Bromo-3',4'-(methylenedioxy)propiophenone Usage And Synthesis

Chemical Properties

Pale Yellow Solid

Uses

1-(benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one (2-Bromo-3',4'-(methylenedioxy)propiophenone) can be used in the preparation of antifungal agents and MDMA analogs.

Application

2-Bromo-3',4'-(methylenedioxy)propiophenone, also known as 4′-(methylenedioxy)propiophenone, is an analytical reference standard categorized as a precursor in the synthesis of cathinones. This product is intended for research and forensic applications.

Synthesis

Bromine (10.0 mmol) was added to a solution of the ketone (10.0 mmol) in Et2O (25 mL). The solution was stirred for 30 min (until the color of the solution changed from red to light-yellow). Then, the reaction was quenched with water (10 mL), and the mixture was diluted with Et2O (25 mL). The organic layer was washed with a saturated solution of aqueous NaHCO3 (30 mL), a saturated solution of aqueous Na2S2O3 (30 mL), and brine (30 mL), and then it was dried over MgSO4, filtered, and concentrated. The α-bromoketone was purified by flash chromatography on silica gel. 2-Bromo-3',4'-(methylenedioxy)propiophenone [52190-28-0]. This compound was prepared according to the General Procedure from 3,4-methylenedioxypropiophenone (1.78 g, 10.0 mmol). The product was obtained as a white solid (eluted with 50% CH2Cl2 in hexanes; 2.13 g, 82% yield). 1H NMR (CDCl3, 500 MHz) δ 7.64 (d, J= 8.0 Hz, 1H), 7.49 (s, 1H), 6.87 (d, J= 8.0 Hz, 1H), 6.07 (s, 2H), 5.21 (q, J= 7.0 Hz, 1H), 1.88 (d, J= 7.0 Hz, 3H).