| Identification | More | [Name]
3-Amino-1,2-benzisoxazole | [CAS]
36216-80-5 | [Synonyms]
1,2-BENZISOXAZOL-3-AMINE
AKOS BBS-00002920
BENZO[D]ISOXAZOL-3-YLAMINE
IFLAB-BB F1935-0009
OTAVA-BB BB7119710108
3-Amino-1,2-benzisoxazole
3-Amino-1,2-benzisoxazole 97%
1,2-Benzisoxazol-3-amine ,97%
1,2-Benzoisoxazol-3-amine | [Molecular Formula]
C7H6N2O | [MDL Number]
MFCD03407353 | [Molecular Weight]
134.14 | [MOL File]
36216-80-5.mol |
| Chemical Properties | Back Directory | [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 | [Detection Methods]
HPLC | [Stability:]
Hygroscopic | [CAS DataBase Reference]
36216-80-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S37/39:Wear suitable gloves and eye/face protection . | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29349990 |
| Hazard Information | Back Directory | [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 |
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