5-Bromobenzo[c][1,2,5]oxadiazole Chemical Properties

Melting point:

72 °C

Boiling point:

255.8±32.0 °C(Predicted)

Density 

1.826±0.06 g/cm3(Predicted)

storage temp. 

Room temperature.

pka

-1.63±0.36(Predicted)

form 

Solid

CAS DataBase Reference

51376-06-8

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

Hazard Note 

Irritant

HS Code 

2934999090

5-Bromobenzo[c][1,2,5]oxadiazole Usage And Synthesis

Uses

5-Bromobenzo[c][1,2,5]oxadiazole, also known as 5-Bromo-2,1,3-benzoxadiazole, is a heterocyclic compound. It can be used as a pharmaceutical intermediate in drug synthesis. It is a derivative of benzo[c][1,2,5]oxadiazole which is a strong electron‐withdrawing unit compared to benzo[c][1,2,5]thiadiazole (BT). Hence BO is usually introduced as an acceptor to construct narrow band-gap donor-acceptor (D-A) materials[1]. BO is incorporated into the naphthalenediimide (NDI) based polymer backbone to improve the performance of polymer semiconductor.

Preparation

Triphenylphosphine (1.1 mmol) was dissolved in dry toluene (3 mL) and stirred at 110°C under argon atmosphere; then 6-bromobenzo[c][1,2,5]oxadiazole 1-oxide (1 mmol) in toluene (0.5 mL) was added dropwise over 1 hour and the resulting mixture was stirred for 3 hours. After completion, the solvent was evaporated in vacuo, and the crude was purified through flash column chromatography (cyclohexane - diethyl ether 98:2) to afford 5-Bromobenzo[c][1,2,5]oxadiazole which is a pale pink solid.

References

[1] Song X, et al. Fusing Benzo[c][1,2,5]oxadiazole Unit with Thiophene for Constructing Wide-bandgap High-performance IDT-based Polymer Solar Cell Donor Material. Macromolecular Rapid Communications, 2018; 39: 1700782.

5-Bromobenzo[c][1,2,5]oxadiazole(51376-06-8)Related Product Information

• Dibenzothiophene
• Thianaphthene
• 6-Chloro-2-benzoxazolethiol
• 5-BROMO[1,2,5]THIADIAZOLO[3,4-E][2,1,3]BENZOXADIAZOLE 3-OXIDE
• 5-Bromobenzo[c][1,2,5]oxadiazole