Benzene, 1-(1-broMoethyl)-4-nitro-
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Benzene, 1-(1-broMoethyl)-4-nitro-
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CAS No:
19935-81-0
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Formula:
C8H8BrNO2
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Chemical Name:
Benzene, 1-(1-broMoethyl)-4-nitro-
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Synonyms:
1-(1-Bromoethyl)-4-nitrobenzene;1-(1-bromo-ethyl)-4-nitro-benzene;Benzene, 1-(1-bromoethyl)-4-nitro-;methyl 4-nitro benzyl bromide;SCHEMBL678502;1-(4-nitrophenyl)ethyl bromide;DTXSID80452200;AKOS009437324;DS-5576;NE48559
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CAS No:
Benzene, 1-(1-broMoethyl)-4-nitro- Use and Manufacturing
Asolution of 1-ethyl-4-nitrobenzene (10.0 g, 66 mmol), N-bromosuccinamide (11.8g, 66 mmol) and benzoyl peroxide (160 mg, 0.66 mmol) in CCIGeneral procedure: To a solution of aromatic compound 1a-q (1 mmol) in CH3CN (6 mL) and H2O (0.5 mL) were added KBr (0.5 mmol) and Oxone (2.2 mmol), and the mixture was stirred at 45°C. After completion (monitored by TLC), the reaction mixture was filtered and the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, washed with saturated aqueous Na2S2O3 and brine, dried over anhydrous Na2SO4. Removal of the solvent under vacuum afforded the crude product, which was purified by column chromatography using hexane/ethyl acetate as eluent (20 - 80 : 1).A mixture of 1-ethyl-4-nitro-benzene (3.4 mL, 25 mmol), N-bromosuccinimide (4.38 g, 24.6 mmol) and benzoylperoxide (0.04g, 0.18 mmol) in carbon tetrachloride (30 mL) was refluxed 1h, cooled and filtered, washing with 1:1 ethyl acetate : hexanes. The filtrate was evaporated and purified by flash chromatography (SiO2) eluted with 2:98 ethyl acetate : hexanes to provide 1-(1-bromo-ethyl)-4-nitro-benzene (5.18 g, 90percent yield) as a yellow oil. 1H-NMR (CDCl3, 500 MHz) 8.22 (d, 2H), 7.62 (d, 2H), 5.22 (q, 1H), 2.08 (d, 3H) ppm; HPLC (Method A) 3.837 min.
Computed Properties
Molecular Weight:230.06
XLogP3:3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:228.97384
Monoisotopic Mass:228.97384
Topological Polar Surface Area:45.8
Heavy Atom Count:12
Complexity:161
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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