2,3-DIBROMOQUINOLINE

2,3-DIBROMOQUINOLINE Property

Melting point:

77 °C

Boiling point:

332.5±22.0 °C(Predicted)

Density 

1.923±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

-1.97±0.50(Predicted)

Appearance

Off-white to yellow Solid

Safety

HazardClass 

IRRITANT

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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

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

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

2,3-DIBROMOQUINOLINE Chemical Properties,Usage,Production

Application

2,3-Dibromoquinoline is a heterocyclic organic compound that can be used as a pharmaceutical intermediate.

Synthesis

General procedure for the synthesis of 2,3-dibromoquinoline from 3-bromoquinoline: To a stirred solution of 3-bromoquinoline (306 mg, 1.47 mmol) in dichloromethane (3 mL) was added m-chloroperoxybenzoic acid (m-CPBA, 358 mg, 85% max, 1.76 mmol) at 0 °C and the reaction was stirred overnight at room temperature. Additional dichloromethane (11.6 mL) was added to the reaction mixture. Phosphorus tribromide oxide (POBr3, 516 mg, 1.76 mmol) was added to the resulting solution at 0 °C, followed by dropwise addition of N,N-dimethylformamide (DMF, 57 μL, 0.74 mmol) under argon protection. The reaction mixture was gradually warmed to 25 °C and stirred for 2 h, after which additional dichloromethane (10 mL) was added. Saturated aqueous sodium carbonate solution was slowly added to the reaction mixture and the pH was adjusted to 7-8. The resulting mixture was separated and the aqueous phase was thoroughly extracted with dichloromethane. The organic phases were combined, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (petroleum ether: ethyl acetate = 100:1) to afford 2,3-dibromoquinoline (335 mg, 79% yield) as a white solid.

References

[1] Tetrahedron, 2016, vol. 72, # 38, p. 5762 - 5768
[2] Organic Letters, 2007, vol. 9, # 26, p. 5525 - 5528