3-Amino-1,2-benzisoxazole Chemical Properties

Melting point:

110 °C

Boiling point:

311.6±15.0 °C(Predicted)

Density 

1.317±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

2.04±0.30(Predicted)

color 

White to Off-White

Stability:

Hygroscopic

CAS DataBase Reference

36216-80-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38-36-25

Safety Statements 

26-36/37/39-37/39-45

HazardClass 

IRRITANT

HS Code 

29349990

3-Amino-1,2-benzisoxazole Usage And Synthesis

Chemical Properties

White to light brown solid

Uses

1,2-Benzisoxazol-3-amine is a useful reagent for the preparation of benzisoxazole sulfonamides useful in treatment of diseases

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 26, p. 1293, 1989 DOI: 10.1002/jhet.5570260515

Synthesis

General procedure for the synthesis of 1,2-benzisoxazol-3-amine from 2-fluorobenzonitrile: (1) Synthesis of 1,2-benzisoxazol-3-amine: potassium tert-butoxide (14.9 g, 133 mmol) was added to a solution of N,N-dimethylformamide (150 ml) containing acetohydroxamic acid (10.0 g, 133 mmol), and stirred for 30 min at room temperature. Subsequently 2-fluorobenzonitrile (18.0 g, 133 mmol) was added and the reaction continued to be stirred at room temperature for 5 hours. After completion of the reaction, the mixture was poured into water and extracted with ethyl acetate. The organic phases were combined, washed with water and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure and the residue was recrystallized from hexane to give 4.80 g (27.0% yield) of the target product 1,2-benzisoxazol-3-amine as a solid. The product was characterized by 1H-NMR (CDCl3): δ 4.43 (2H, br s), 7.23-7.28 (1H, m), 7.43 (1H, d, J = 9.3Hz), 7.50-7.56 (2H, m).

References

[1] Patent: EP1813606, 2007, A1. Location in patent: Page/Page column 24
[2] Journal of Organic Chemistry, 2000, vol. 65, # 10, p. 2924 - 2932
[3] Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1293 - 1298
[4] Patent: EP2460799, 2012, A1
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 18, p. 6157 - 6165

3-Amino-1,2-benzisoxazole(36216-80-5)Related Product Information

• p-Phenylenediamine
• 3-Aminopyridine
• Glycine
• o-Phenylenediamine
• ISOXAFLUTOLE
• Betaine
• Aniline
• Sulfamethoxazole
• Isoxazole
• ALTRENOGEST
• Tamoxifen
• Sulfisoxazole
• 2,1-BENZISOXAZOLE
• m-Phenylenediamine
• Bis(2-ethylhexyl)amine
• 3-AMINO-5-NITRO-1,2-BENZISOXAZOLE
• 6-BROMOBENZO[D]ISOXAZOL-3-YLAMINE
• (5-AMINOBENZO[D]ISOXAZOL-3-YL)CARBAMIC ACID TERT-BUTYL ESTER