5-BROMO-2-BENZOXAZOLINONE 97 Chemical Properties

Melting point:

218-222 °C(lit.)

Boiling point:

10.85°C (rough estimate)

Density 

1.809

refractive index 

1.6120 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

8.46±0.70(Predicted)

color 

White to Yellow to Orange

InChI

InChI=1S/C7H4BrNO2/c8-4-1-2-6-5(3-4)9-7(10)11-6/h1-3H,(H,9,10)

InChIKey

DMHTZWJRUUOALC-UHFFFAOYSA-N

SMILES

O1C2=CC=C(Br)C=C2NC1=O

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36

Safety Statements 

26

WGK Germany 

3

RTECS 

DM4950000

HS Code 

2934.99.4400

5-BROMO-2-BENZOXAZOLINONE 97 Usage And Synthesis

Chemical Properties

White to off-white crystalline solid

Synthesis

General procedure for the synthesis of 5-bromo-2(3H)-benzoxazolone from 2-amino-4-bromophenol and N,N'-carbonyldiimidazole: Referring to Example 2, to a solution of 2-amino-4-bromophenol (3.50 g, 18.6 mmol) in tetrahydrofuran (100 mL) was slowly added N,N'-carbonyldiimidazole (3.62 g, 22.3 mmol). The reaction mixture was heated to reflux for 1.5 hours. Upon completion of the reaction, the reaction solution was cooled to 20-25 °C, acidified by addition of 2N aqueous hydrochloric acid and subsequently extracted with ethyl acetate. The organic layers were combined and washed sequentially with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, then dried with anhydrous sodium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure to give 5-bromo-1,3-benzoxazol-2(3H)-one (3.89 g, quantitative yield).IR (cm-1): 960, 1149, 1474, 1622, 1751.

References

[1] Patent: EP1719761, 2006, A1. Location in patent: Page/Page column 26
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 18, p. 5568 - 5582
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 20, p. 8191 - 8195
[4] Synthesis (Germany), 2013, vol. 45, # 23, p. 3269 - 3275
[5] Patent: WO2013/64984, 2013, A1. Location in patent: Page/Page column 125

5-BROMO-2-BENZOXAZOLINONE 97(14733-73-4)Related Product Information

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• 2-Chlorobenzoxazole
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• 5-BROMO-2-METHOXYANILINE
• 5,7-DIBROMOBENZO[D]OXAZOL-2(3H)-ONE