6-BROMOBENZO[D]ISOXAZOL-3-YLAMINE Chemical Properties

Boiling point:

371.1±22.0 °C(Predicted)

Density 

1.804±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

0.72±0.30(Predicted)

Appearance

Off-white to light brown Solid

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2934999090

6-BROMOBENZO[D]ISOXAZOL-3-YLAMINE Usage And Synthesis

Uses

6-Bromobenzo[D]Isoxazol-3-Amine is a useful research reagent for organic synthesis.

Synthesis

Step A: 6-Bromobenzo[d]isoxazol-3-amine (1.13 g, 15.0 mmol) and N-hydroxyacetamide were dissolved in N,N-dimethylformamide (DMF, 20 mL). Potassium tert-butoxide (KOt-Bu, 1.68 g, 15.0 mmol) was added to the reaction system and stirred at room temperature for 30 min. Subsequently, 4-bromo-2-fluorobenzonitrile (2.0 g, 10.0 mmol) was added and the reaction was continued at room temperature for 2 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (50 mL) and water (50 mL). The aqueous layer was separated and extracted with ethyl acetate. The organic phases were combined, washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by fast column chromatography using ethyl acetate/hexane (1:4, v/v) and ethyl acetate/hexane (1:3, v/v) sequentially as eluent to afford the target compound 3-amino-6-bromobenzo[D]isoxazole (1.35 g, 63% yield). Mass spectra (APCI) m/z: 215.2, 217.1 ([M+H]+).

References

[1] Tetrahedron Letters, 1996, vol. 37, # 17, p. 2885 - 2886
[2] Patent: US2007/49603, 2007, A1. Location in patent: Page/Page column 61-62
[3] Patent: WO2010/51042, 2010, A1. Location in patent: Page/Page column 135
[4] Patent: WO2014/151147, 2014, A1. Location in patent: Paragraph 00502
[5] Patent: US2014/357651, 2014, A1. Location in patent: Paragraph 0485

6-BROMOBENZO[D]ISOXAZOL-3-YLAMINE(177995-39-0)Related Product Information

• 3-AMINO-4-CYANOPYRIDINE
• 3-AMINO-6-BROMOPYRAZINE-2-CARBONITRILE
• 3-aMino-5-broMo-4-chloropyridine
• 3-Amino-6-trifluoromethyl-pyridin-2-ol
• 3-AMINO-6-IODOPYRAZINE-2-CARBOXYLIC ACID METHYL ESTER
• 3-amino-6-chloropyrazine-2-carboxylic acid
• 3-AMINO-4-METHOXYPYRIDINE
• 3-AMINO-3-(4-CYANOPHENYL)PROPANOIC ACID
• 3-Amino-5-chloropyridin-2-ol HCl
• (3-aminopyrazin-2-yl)methanol
• 3-Amino-3-(4-methoxyphenyl)propionic acid
• 3-PYRIDINAMINE, 6-(1-METHYLETHYL)-
• 3-AMINO-5-HYDROXYBENZOIC ACID
• 2-CHLORO-5-IODO-PYRIDIN-3-YLAMINE
• 2-CHLORO-5-(TRIFLUOROMETHYL)-3-PYRIDINAMINE
• 7-Bromobenzo[d]isoxazol-3-amine
• 3-Amino-1,2-benzisoxazole
• 6-BROMOBENZO[D]ISOXAZOL-3-YLAMINE