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

5-Bromobenzo[c][1,2,5]oxadiazole Structure
CAS No.
51376-06-8
Chemical Name:
5-Bromobenzo[c][1,2,5]oxadiazole
Synonyms
BUTTPARK 85\04-54;5-Bromobenzofurazan,97%;5-BROMO-2,1,3-BENZOXADIAZOLE;2,1,3-Benzoxadiazole,5-bromo-;5-BROMOBENZO[1,2,5]OXA-DIAZOLE;5-Bromobenzo[c][1,2,5]oxadiazole
CBNumber:
CB0189006
Molecular Formula:
C6H3BrN2O
Molecular Weight:
199
MOL File:
51376-06-8.mol
Modify Date:
2024/7/9 21:58:15

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

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P280g-P305+P351+P338
Hazard Codes  Xi,Xn
Risk Statements  22
Hazard Note  Irritant
HS Code  2934999090
NFPA 704
0
2 0

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

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.
5-BROMO-2,1,3-BENZOXADIAZOLE

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 Preparation Products And Raw materials

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5-BROMOBENZO[1,2,5]OXA-DIAZOLE 5-BROMO-2,1,3-BENZOXADIAZOLE BUTTPARK 85\04-54 2,1,3-Benzoxadiazole,5-bromo- 5-Bromobenzofurazan,97% 5-Bromobenzo[c][1,2,5]oxadiazole 51376-06-8 C6H3BrN2O Heterocyclic Building Blocks