4-BROMO-2-(TRIFLUOROMETHYL)BENZONITRILE
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4-BROMO-2-(TRIFLUOROMETHYL)BENZONITRILE
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CAS No:
191165-13-6
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Formula:
C8H3BrF3N
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Chemical Name:
4-BROMO-2-(TRIFLUOROMETHYL)BENZONITRILE
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Synonyms:
4-BROMO-2-(TRIFLUOROMETHYL)BENZONITRILE;3-Bromo-6-cyanobenzotrifluoride;5-Bromo-2-cyanobenzotrifluoride;4-Bromo-2-(trifluoromethyl)benzonitrile ,98%;Benzonitrile, 4-broMo-2-(trifluoroMethyl)-;5-Bromo-2-cyanobenzotrifluoride, 4-Bromo-alpha,alpha,alpha-trifluoro-o-tolunitrile
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CAS No:
4-BROMO-2-(TRIFLUOROMETHYL)BENZONITRILE Basic Attributes
250.02
248.940094
DTXSID90624956
2926909090
Safety Information
P260, P261, P264, P270, P271, P280, P284, P301+P310, P302+P352, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501
H301
|Danger|H301+H311+H331 (20%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]|P260, P261, P264, P270, P271, P280, P284, P301+P310, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P310, P311, P312, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 5 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
4-BROMO-2-(TRIFLUOROMETHYL)BENZONITRILE Use and Manufacturing
To a solution of 4-amino-2-(trifluoromethyl)benzonitrile 29 (1.02 g, 5.48 mmol) in acetonitrile (30 mL) was added tert-butyl nitrite (0.95 mL, 7.19 mmol) dropwise at 0 °C. After stirring at 0 °C for 0.5 h, copper (II) bromide (1.39 g, 6.22 mmol) was added and the mixture was warmed to room temperature. The mixture was stirred at room temperature for 14 h, poured into brine, and extracted with EtOAc. The organic layer was dried over anhydrous MgSOGeneral procedure: 4-Cyano-3-(substituted) aniline 4a or 4b (38 mmol) was dissolved in conc. HCl (27 ml). After cooling to 0 C, sodium nitrite (39 mmol, 1.5 eq) was added very slowly to the stirred solution with the temperature being kept within (0 and 5 °C). This diazonium salt solution was then poured into a flask containing CuBr (53 mmol, 1.4 eq) and 22 ml of conc. HCl. The solution was stirred for 2 h, and then, the reaction mixture was poured into ice water (50 ml) extracted with Ethyl acetate (100 ml). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (2 x 50 ml). The combined extracts were washed with saturated aqueous NaHCO3 solution (1 x 150 ml), brine (3 x 100 ml) and dried over Na2SO4. The resulting material was concentrated, and the residue was purified by silica gel chromatography (petroleum ether:ethyl acetate, 10:1) to afford the title compound (5a or 5b) as white solid (72–75 percent yield). 4-Bromo-2-(trifluoromethyl) benzonitrile (5a) Yield 75 percent; White Solid; IR (KBr) ν max: 3101, 3040 (C–Harom), 2924, 2853 (C–Halk), 2235 (C:N), 1594, 1558, 1542, 1508, 1484, 1405 (C=Carom), 1182, 1142, 1057 (C–Hbend), 1304, 1270, 551 (C–CF3) cm-1; 1H NMR (400 MHz, CDCl3, ppm): δ 7.96 (s, 1H, H-2), d 7.87 (d, J = 8.0 Hz, 1H, H-6), 7.74 (d, J = 8.0 Hz, 1H, H-5); 13C NMR (100 MHz, CDCl3, ppm): δ 135.8 (C6), 134.4, 133.8 (q, J = 65.5 Hz, C2), 130.3 (q, CF3), 128.2 (d, J = 26 Hz, C5), 122.9 (C3), 120.2 (C4), 114.8 (CN), 108.9 (C1); HRMS (ESI): m/z Calcd for C8H3 79BrF3N [M'H]?: 249. 94737 Found: 249.94696; Calcd for C8H3 81BrF3N [M'H]?: 251.94520; Found: 251.94479.Examples 1 and 2; 4-bromo-2-(trifluoromethyl) benzonitrileIntermediate lb; To a solution of 4-amino-2-(trifluoromethyl) benzonitrile (la) (5.0 g, 26.9 mmol) in CH
Computed Properties
Molecular Weight:250.01
XLogP3:3.2
Hydrogen Bond Acceptor Count:4
Exact Mass:248.94010
Monoisotopic Mass:248.94010
Topological Polar Surface Area:23.8
Heavy Atom Count:13
Complexity:229
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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4-BROMO-2-(TRIFLUOROMETHYL)BENZONITRILE
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