| Identification | Back Directory | [Name]
5-bromo-2-nitrobenzenamine | [CAS]
5228-61-5 | [Synonyms]
5-bromo-2-nitroanline
5-bromo-2-nitrobenzenamine
2-Amino-4-bromonitrobenzene
(5-BroMo-2-nitrophenyl)aMine
BenzenaMine, 5-broMo-2-nitro- | [Molecular Formula]
C6H5BrN2O2 | [MDL Number]
MFCD09056836 | [MOL File]
5228-61-5.mol | [Molecular Weight]
217.02 |
| Chemical Properties | Back Directory | [Melting point ]
151-152 °C | [Boiling point ]
331.9±22.0 °C(Predicted) | [density ]
1.812±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [form ]
solid | [pka]
-1.53±0.25(Predicted) | [color ]
Light yellow to yellow | [InChI]
InChI=1S/C6H5BrN2O2/c7-4-1-2-6(9(10)11)5(8)3-4/h1-3H,8H2 | [InChIKey]
RMIFLIVHJLREFJ-UHFFFAOYSA-N | [SMILES]
C1(N)=CC(Br)=CC=C1[N+]([O-])=O |
| Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of 2-nitro-5-bromoaniline from 1-bromo-4-nitrobenzene:
Step 1: Synthesis of 5-bromo-2-nitroaniline (142)
[0745] To a solution of ethylene glycol dimethyl ether (170 mL) containing potassium tert-butoxide (21.92 g, 195 mmol) and copper(I) chloride (2.36 g, 23.8 mmol) was added dropwise a solution of 1-bromo-4-nitrobenzene (141, 8.69 g, 43.0 mmol) in DMF (45 mL) at 0 °C and protected by nitrogen, the time of dropwise addition was 50 min. After the dropwise addition, the cooling bath was removed and the reaction mixture was continued to be stirred at room temperature for 4 hours. After completion of the reaction, the reaction solution was diluted with dichloromethane, washed sequentially with aqueous ammonium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated to give the target compound 142 (7.85 g, 84% yield).
[0746] 1H NMR (CDCl3) δ (ppm): 7.98 (d, J = 9.2 Hz, 1H), 7.02 (d, J = 2.0 Hz, 1H), 6.82 (dd, J = 9.2, 2.0 Hz, 1H), 6.12 (bs, 2H). | [References]
[1] Patent: WO2007/118137, 2007, A1. Location in patent: Page/Page column 109-110
[2] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 11, p. 1437 - 1444
[3] Patent: WO2016/89830, 2016, A1. Location in patent: Page/Page column 43
[4] Patent: WO2016/89797, 2016, A1. Location in patent: Page/Page column 65
[5] Patent: WO2016/89833, 2016, A1. Location in patent: Page/Page column 42 |
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