| Identification | Back Directory | [Name]
5-BROMO-2-CHLORONITROBENZENE | [CAS]
16588-24-2 | [Synonyms]
5-BROMO-2-CHLORONITROBENZENE
2-chloro-5-bromonitrobenzene
4-BROMO-1-CHLORO-2-NITROBENZENE
Benzene, 4-broMo-1-chloro-2-nitro-
4-Bromo-1-chloro-2-nitrobenzene > | [Molecular Formula]
C6H3BrClNO2 | [MDL Number]
MFCD05863216 | [MOL File]
16588-24-2.mol | [Molecular Weight]
236.45 |
| Chemical Properties | Back Directory | [Melting point ]
0°C | [Boiling point ]
0°C | [density ]
2.035 g/cm3(Temp: 16 °C) | [Fp ]
0°C | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [color ]
White to Light yellow | [λmax]
313nm(H2O)(lit.) | [CAS DataBase Reference]
16588-24-2 |
| Hazard Information | Back Directory | [Uses]
4-Bromo-1-chloro-2-nitrobenzene (5-Bromo-2-chloronitrobenzene) is a pharmaceutical intermediate compound used in the preparation of vismodegib, a molecular inhibitor of the Hedgehog signalling pathway approved for the treatment of metastatic and locally advanced basal cell carcinoma (BCC). | [Synthesis]
General procedure for the synthesis of 5-bromo-2-chloronitrobenzene from 3-nitro-4-chloroaniline: 4-chloro-3-nitroaniline (17.2 g, 0.1 mol) was dissolved in 260 mL of 48% hydrobromic acid (HBr) at 0 °C. Subsequently, an aqueous solution of sodium nitrite (NaNO2, 13.8 g, 0.2 mol) was added slowly and dropwise. The reaction mixture was stirred continuously for 1 h at 0 °C. After that, cuprous bromide (CuBr, 24 g, 0.17 mol) was added in batches and stirring was continued for 1 hour at 0°C. Upon completion of the reaction, water was added and the mixture was gradually warmed to room temperature and extracted with ethyl acetate (EtOAc). The crude product was purified by silica gel column chromatography to give the final 5-bromo-2-chloronitrobenzene (13 g, 55% yield). The structure of the product was confirmed by 1H NMR (CDCl3, 400 MHz): δ 8.03-8.02 (m, 1H), 7.66-7.63 (m, 1H), 7.45-7.42 (m, 1H). | [References]
[1] Patent: WO2013/117522, 2013, A1. Location in patent: Page/Page column 40
[2] Patent: US2015/18367, 2015, A1. Location in patent: Paragraph 0177; 0178
[3] Journal of the American Chemical Society, 1962, vol. 84, p. 1026 - 1032
[4] Journal of Organic Chemistry USSR (English Translation), 1967, vol. 3, p. 1795 - 1799
[5] Zhurnal Organicheskoi Khimii, 1967, vol. 3, # 10, p. 1839 - 1843 |
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