1,2-DIBROMO-4,5-(METHYLENEDIOXY)BENZENE

1,2-DIBROMO-4,5-(METHYLENEDIOXY)BENZENE Property

Melting point:

83-85°C

Boiling point:

294.7±40.0 °C(Predicted)

Density 

2.104±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMF: 30 mg/ml; DMSO: 30 mg/ml; DMSO:PBS (pH 7.2) (1:2): 0.33 mg/ml; Ethanol: 10 mg/ml

form 

A crystalline solid

color 

Off-white to light brown

BRN 

145633

Safety

Hazard Codes 

Xi

Safety Statements 

22-24/25

HS Code 

2932.99.7000

HazardClass 

IRRITANT

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

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

P271Use only outdoors or in a well-ventilated area.

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

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

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

1,2-DIBROMO-4,5-(METHYLENEDIOXY)BENZENE Chemical Properties,Usage,Production

Uses

1,2-Dibromo-4,5-methylenedioxybenzene is an impurity in the synthesis of amphetamines[1].

Synthesis

Dichloromethane (762 μL, 11.94 mmol) was added dropwise to a stirred solution of 4,5-dibromobenzene-1,2-diol (2.00 g, 7.46 mmol) and cesium carbonate (3.89 g, 11.94 mmol) in N,N-dimethylformamide (DMF, 75 mL), and the reaction was carried out at room temperature. Subsequently, the reaction mixture was heated to 120 °C and maintained for 2 h, after which it was cooled to room temperature. Upon completion of the reaction, the reaction was quenched by the addition of water (150 mL), and the resulting solution was extracted several times with ethyl acetate (EtOAc, 5 × 100 mL). The organic phases were combined, washed sequentially with water (5×150 mL) and saturated brine (2×150 mL), dried over anhydrous sodium sulfate (Na2SO4), and concentrated under reduced pressure to remove the solvent. Finally, the product was purified by silica gel column chromatography eluting with a gradient of petroleum ether (PET)/ethyl ether (Et2O) (100:0 to 95:5) to afford 5,6-dibromobenzo[d][1,3]dioxole (1.54 g, 5.50 mmol, 74% yield) as a white crystalline solid.

References

[1] Heather E, et al. Organic impurity profiling of 3,4-methylenedioxymethamphetamine (MDMA) synthesised from catechol. Forensic Sci Int. 2015 Mar;248:140-7. DOI:10.1016/j.forsciint.2014.12.021