| Identification | More | [Name]
5'-BROMO-2'-HYDROXY-3'-NITROACETOPHENONE | [CAS]
70978-54-0 | [Synonyms]
1-(5-BROMO-2-HYDROXY-3-NITROPHENYL)ETHANONE
3-BROMO-6-HYDROXY-5-NITRO ACETOPHENONE
5'-BROMO-2'-HYDROXY-3'-NITROACETOPHENONE
5-BROMO-2-HYDROXY-3-NITROACETOPHENONE
5'-Bromo-3'-nitro-2'-hydroxyacetophenone | [Molecular Formula]
C8H6BrNO4 | [MDL Number]
MFCD01631134 | [Molecular Weight]
260.04 | [MOL File]
70978-54-0.mol |
| 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:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
29145090 |
| Hazard Information | Back Directory | [Uses]
5'-Bromo-2'-hydroxy-3'-nitroacetophenone is used as a chemical reagent in the synthesis of amides and benzoxazoles directly using a sulfate catalyst and microwaves. 1-(5-Bromo-2-hydroxy-3-nitrophen yl)ethanone is used in studies involving HIV-1 integrase inhibitors.
| [Preparation]
Preparation by nitration of 5-bromo-2-hydroxyacetophenone in refluxing carbon tetrachloride (88%). | [Synthesis]
1. Synthesis of 5-bromo-2-hydroxy-3-nitroacetophenone
To a solution of 5-bromo-2-hydroxyacetophenone (23.7 g, 0.110 mol) in carbon tetrachloride (90 mL) was slowly added concentrated nitric acid (17.2 mL). The reaction mixture was stirred at 75 °C for 50 min and subsequently cooled to room temperature. The precipitated solid was collected by filtration and washed with cold carbon tetrachloride. After vacuum drying, 20.9 g of the target product 5-bromo-2-hydroxy-3-nitroacetophenone was obtained as a light yellow solid in 73% yield.
1H NMR (300 MHz, CDCl3) δ: 2.73 (s, 3H), 8.14 (d, 1H), 8.31 (d, 1H), 12.92 (s, 1H). | [References]
[1] Patent: US5990142, 1999, A
[2] Patent: EP1391451, 2004, A1. Location in patent: Page 113
[3] Patent: WO2017/221002, 2017, A1. Location in patent: Page/Page column 92 |
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