4-(BROMOMETHYL)-2-FLUOROBENZONITRILE
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4-(BROMOMETHYL)-2-FLUOROBENZONITRILE
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CAS No:
222978-03-2
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Formula:
C8H5BrFN
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Chemical Name:
4-(BROMOMETHYL)-2-FLUOROBENZONITRILE
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Synonyms:
4-CYANO-3-FLUOROBENZYL BROMIDE;4-(BROMOMETHYL)-2-FLUOROBENZONITRILE;4-Cyano-3-fluorobenzyl bromide 98%;4-Cyano-3-fluorobenzylbromide98%;4-(Bromomethyl)-2-fluorobenzonitrile 98%;4-Cyano-3-fluorobenzyl bromide, alpha-Bromo-2-fluoro-p-tolunitrile;Benzonitrile, 4-(bromomethyl)-2-fluoro-
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CAS No:
Characteristics
23.8
2.3
1.6±0.1 g/cm3
44-45 °C
275.6°C at 760 mmHg
120.5±24.6 °C
1.564
0.00505mmHg at 25°C
Safety Information
20/21/22
36/37
C,Xn
Corrosive/Lachrymatory
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P501
H302+H312+H332
|Warning|H302+H312+H332 (97.44%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
4-(BROMOMETHYL)-2-FLUOROBENZONITRILE Use and Manufacturing
3-fluoro-4-nitrile toluene 1 (10 g, 74.07 mmol)Dissolved in chloroform 200mL, Add BPO 1g, stirring dissolved, NBS (19.77 g, 11.11 mmol) was added portionwise, Reflux 12h, Cooling, the reaction solution with saturated aqueous solution of sodium bicarbonate 3 times wash, Wash the amount of water 3 times, the amount of saturated salt water washed 3 times, evaporation of the solvent under reduced pressure, column chromatography was pale yellow liquid 14.00g, yield88.79percent.To the solution of 83 2-fluoro-4-methylbenzonitrile 16 (10g, 74.07mmol) in 73 CHClTo a solution of 2-fluoro-4-methyl-benzonitrile (1.45 g, 10.7 mmol) in CClStep E Preparation of 2-fluoro-4-imidazol-1-ylmethyl-benzonitrile 4-Bromomethyl-2-fluoro-benzonitrile (3.44 g, 16.0 mmol) and imidazole (5.47 g, 80.3 mmol) were dissolved in DMF (40 mL) and stirred at ambient temperature for 2 h. The DMF was removed in vacuo and the residue was partitioned between EtOAc (300 mL) and aqueous saturated NaHCO3 solution. The organic layer was separated, washed with NaHCO3 solution, H2O, brine, and dried (MgSO4). Filtration and concentration to dryness gave the title compound after chromatography (silica gel, 1-2% CH3OH/CH2Cl2). 1H NMR (CDCl3) delta 7.62 (dd, 1H, J=8.5, 9.5 Hz), 7.57 (s, 1H), 7.16 (s, 1H), 7.00 (d, 1H, J=8.5 Hz), 6.94 (d, 1H, J=9.5 Hz), 6.91 (s, 1H), 5.21 (s, 2H).Step E Preparation of 2-Fluoro-4-imidazol-1-ylmethyl-benzonitrile 4-Bromomethyl-2-fluoro-benzonitrile (3.44 g, 16.0 mmol) and imidazole (5.47 g, 80.3 mmol) were dissolved in DMF (40 mL) and stirred at ambient temperature for 2 h. The DMF was removed in vacuo and the residue was partitioned between EtOAc (300 mL) and aqueous saturated NaHCO3 solution. The organic layer was separated, washed with NaHCO3 solution, H2O, brine, and dried (MgSO4). Filtration and concentration to dryness gave the title compound after chromatography (silica gel, 1-2% CH3OH/CH2Cl2). 1H NMR (CDCl3) d 7.62 (dd, 1H, J=8.5, 9.5 Hz), 7.57 (s, 1H), 7.16 (s, 1H), 7.00 (d, 1H, J=8.5 Hz), 6.94 (d, 1H, J=9.5 Hz), 6.91 (s, 1H), 5.21 (s, 2H).
4-(BROMOMETHYL)-2-FLUOROBENZONITRILE
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