3,7-Dibromo-1,5-naphthyridine

3,7-Dibromo-1,5-naphthyridine Property

Boiling point:

326.9±37.0 °C(Predicted)

Density 

2.022±0.06 g/cm3(Predicted)

storage temp. 

Store at room temperature

pka

-0.52±0.30(Predicted)

Appearance

White to off-white Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

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

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

3,7-Dibromo-1,5-naphthyridine Chemical Properties,Usage,Production

Application

3,7-Dibromo-1,5-naphthidine is a pharmaceutical intermediate that can be obtained by brominating 1,5-naphthidine with elemental bromine. 3,7-Dibromo-1,5-naphthidine can be used to prepare an electron transport material.

Synthesis

General procedure for the synthesis of 3,7-dibromo-1,5-naphthyridine from 1,5-naphthyridine: 1. 1,5-naphthyridine (30.80 g, 236.7 mmol) and sodium acetate (38.83 g, 473.3 mmol) were dissolved in acetic acid (236.7 mL) and heated to 60°C. The mixture was then heated to 60°C. The mixture was then heated to 60°C. 2. a solution of bromine (25.6 mL, 496.9 mmol) in acetic acid (35 mL) was added slowly and dropwise over 30 minutes. 3. the reaction mixture is stirred continuously at 60°C for 22 hours. 4. After completion of the reaction, it was cooled to room temperature, diluted with water (250 mL) and alkalized with 4N aqueous NaOH (300 mL), at which time a beige precipitate was produced. 5. The precipitate was collected by filtration and washed with water, methanol and acetone. 6. The resulting solid (54.7 g) was recrystallized from chloroform (1.36 L) to afford a pure cream colored solid 3,7-dibromo-1,5-naphthyridine (30 g, 44% yield). Product characterization: 1H NMR (400 MHz, CDCl3) δ 9.08-8.95 (m, 2H), 8.62 (dd, J = 2.2, 0.7 Hz, 1H), 8.46-8.35 (m, 1H), 8.23 (d, J = 8.8 Hz, 1H), 7.79 (d, J = 8.8 Hz, 1H), 7.69 (dd, J = 8.5, 4.3 Hz, 1H). [M + H]+ = 286.9.

References

[1] Patent: US2014/275548, 2014, A1. Location in patent: Paragraph 0370; 0371