| Identification | More | [Name]
2-BROMO-5-NITROANISOLE | [CAS]
77337-82-7 | [Synonyms]
2-BROMO-5-NITROANISOLE
4-BROMO-3-METHOXYNITROBENZENE
1-BROMO-2-METHOXY-4-NITROBENZENE | [EINECS(EC#)]
278-669-5 | [Molecular Formula]
C7H6BrNO3 | [MDL Number]
MFCD00041250 | [Molecular Weight]
232.03 | [MOL File]
77337-82-7.mol |
| Chemical Properties | Back Directory | [Appearance]
light brown crystalline powder | [Melting point ]
99-103 °C
| [Boiling point ]
302.1±22.0 °C(Predicted) | [density ]
1.640±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [Water Solubility ]
Insoluble in water | [form ]
Crystalline Powder | [color ]
Light brown | [λmax]
324nm(EtOH)(lit.) | [BRN ]
2520496 | [CAS DataBase Reference]
77337-82-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [Hazard Note ]
Irritant | [HS Code ]
29093090 |
| Hazard Information | Back Directory | [Chemical Properties]
light brown crystalline powder | [Synthesis]
General procedure for the synthesis of 2-bromo-5-nitroanisole from 2-methoxy-4-nitroaniline: a catalytic amount of copper bromide (1 mol%) was added to a solution of 2-methoxy-4-nitroaniline (2.5 mmol) in acetonitrile (30 ml), followed by camphorsulfonic acid (3.0 mmol), sodium nitrite or tert-butyl nitrite (3.0 mmol), and tetrabutylammonium bromide (5.0 mmol). The reaction mixture was stirred at 60°C for 24 h (Tables 1 and 2). Nitrogen release was observed immediately during the reaction. After completion of the reaction (confirmed by β-naphthol test and thin layer chromatography), the solvent was removed using a rotary evaporator. The residue was washed with water and extracted with dichloromethane. The organic phases were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. Finally, purification by column chromatography using a hexane/dichloromethane solvent mixture as eluent gave the pure product 2-bromo-5-nitroanisole. The physical properties and 1H NMR data of the product were consistent with the commercially available analytically pure sample. | [References]
[1] Tetrahedron, 2013, vol. 69, # 16, p. 3511 - 3517
[2] Tetrahedron, 2010, vol. 66, # 37, p. 7418 - 7422
[3] Tetrahedron Letters, 2010, vol. 51, # 51, p. 6769 - 6771
[4] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 10, p. 979 - 988
[5] Journal of the American Chemical Society, 1935, vol. 57, p. 1592,1594 |
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