6-BROMO-BENZOXAZOLINONE Chemical Properties

Melting point:

192-196 °C

Boiling point:

-2.6°C (rough estimate)

Density 

1.809

refractive index 

1.6120 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

8.34±0.70(Predicted)

color 

White to Light yellow to Dark green

CAS DataBase Reference

19932-85-5

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36

Safety Statements 

26

WGK Germany 

3

RTECS 

DM4960000

HazardClass 

IRRITANT

HS Code 

29349990

6-BROMO-BENZOXAZOLINONE Usage And Synthesis

Chemical Properties

White solid

Definition

ChEBI: A member of the class of benzoxazoles that is 2-benzoxazolinone substituted at position 6 by a bromo group.

Synthesis

General procedure for the synthesis of 6-bromobenzo[d]oxazol-2(3H)-ones from 2-benzoxazolidinones: 3H-1,3-benzoxazol-2-one (5.00 g, 37.00 mmol) was dissolved in acetic acid (50 mL), and bromine (1.9 mL, 37.0 mmol) was slowly added dropwise. The reaction mixture was stirred at 20°C for 4 hours. After completion of the reaction, the mixture was poured into ice water, the precipitate was collected by filtration, washed with water and dried over air to give a pink solid product (7.48 g, 34.8 mmol, 94% yield). The melting point of the product was 191.6-192.3 °C. 1H NMR (300 MHz, DMSO-d6): δ 11.81 (s, 1H), 7.57 (dd, J=1.9 Hz, 0.3 Hz, 1H), 7.30 (dd, J=8.3 Hz, 1.9 Hz, 1H), 7.04 (dd, J=8.3 Hz, 0.3 Hz, 1H) .13C NMR (75MHz, DMSO-d6): δ154.5, 144.5, 130.3, 126.9, 113.5, 113.2, 111.7.LCMS m/z calculated values [M-H]+: 211.9, 213.9; measured values: 211.8, 213.8.

References

[1] European Journal of Medicinal Chemistry, 2018, vol. 159, p. 104 - 125
[2] Patent: US6372933, 2002, B1. Location in patent: Page column 5 - 6
[3] Patent: US2008/138413, 2008, A1. Location in patent: Page/Page column 22
[4] Monatshefte fur Chemie, 2011, vol. 142, # 1, p. 67 - 80
[5] Patent: EP1251128, 2002, A1. Location in patent: Page 38

6-BROMO-BENZOXAZOLINONE(19932-85-5)Related Product Information

• 2-(Boc-amino)-5-bromopyridine
• 6-CHLORO-BENZOFURAN-3-ONE
• 3-AMINO-6-BROMO-2-CHLOROPYRIDINE
• 2-Bromo-3-hydroxypyridine
• 2-AMINO-5-CHLORO-3-PICOLINE
• 3-BROMO-6-HYDROXY-2-METHYLPYRIDINE
• 2,6-Dibromopyridin-3-amine
• 2-AMINO-5-BROMO-3-IODOPYRIDINE
• 2-Benzoxazolinone
• Benzoxazole
• 2-AMINO-5-BROMOPHENOL
• bromchlorenone
• 2-Benzoxazolinone, 6-bromo-5-chloro-3-(3-chloropropyl)-
• 4-BROMO-2-METHOXY-PHENYLAMINE
• 6-BROMO-BENZOXAZOLINONE