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

storage temp. 

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

Appearance

Off-white to light brown Solid

InChI

InChI=1S/C7H5BrN2O/c8-4-1-2-6-5(3-4)7(9)10-11-6/h1-3H,(H2,9,10)

InChIKey

BGMYWBQEKIMHGU-UHFFFAOYSA-N

SMILES

O1C2=C(C=C(Br)C=C2)C(N)=N1

CAS DataBase Reference

455280-00-9

Safety Information

HS Code 

2934999090

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

Synthesis

3-Amino-5-bromobenzo[d]isoxazoles were synthesized from acetohydroxamic acid and 2-fluoro-5-bromobenzonitrile according to a modified literature method (Palermo, M.G., Tetrahedron Lett, 37: 2885, 1996). The procedure was as follows: in a 50 mL single-neck flask equipped with a magnetic stirrer, N-hydroxyacetamide (2.63 g, 35.0 mmol) and N,N-dimethylformamide (DMF, 100 mL) were added. Subsequently, potassium tert-butoxide (KOtBu, 3.93 g, 35.0 mmol) was added all at once. The reaction system was heated to 300 °C and stirred for 1 h. 5-Bromo-2-fluorobenzonitrile (7 g, 35.0 mmol) was added. Stirring of the reaction mixture was continued overnight. Another portion of potassium tert-butoxide (1.96 g, 17.5 mmol) was added and the solution was stirred again overnight. After completion of the reaction, the mixture was poured into saturated saline and dichloromethane (CH2Cl2) to separate the organic and aqueous phases. The organic phase was dried with anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The residue was purified by fast column chromatography (BIOTAGE system with 0 to 40% ethyl acetate/hexane gradient elution) to afford the target product 3-amino-5-bromobenzo[d]isoxazole (4.59 g, 62% yield) as a colorless solid. The product was confirmed by 1H NMR (500 MHz, DMSO-d6) and LCMS characterization.1H NMR data: δ 8.09 (d, J = 1.8 Hz, 1H), 7.65 (dd, J = 2.1, 8.9 Hz, 1H), 7.45 (d, J = 8.9 Hz, 1H), 6.49 (s, 2H).The LCMS result was in agreement with the calculated value ( C7H5BrN2O) were consistent.

References

[1] Patent: WO2010/138488, 2010, A1. Location in patent: Page/Page column 57-58
[2] Patent: WO2010/51042, 2010, A1. Location in patent: Page/Page column 134
[3] Patent: WO2014/151147, 2014, A1. Location in patent: Paragraph 00502
[4] Patent: US2014/357651, 2014, A1. Location in patent: Paragraph 0485

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