5-Fluoro-2-methylbenzonitrile
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5-Fluoro-2-methylbenzonitrile
structure -
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CAS No:
77532-79-7
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Formula:
C8H6FN
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Chemical Name:
5-Fluoro-2-methylbenzonitrile
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Synonyms:
Benzonitrile, 5-fluoro-2-methyl- (9CI);5-Fluoro-2-methylbenzonitrile,98%;5-Fluoro-2-methylbenzonitrile 98%;5-Fluoro-o-tolunitrile (CN=1);2-cyano-4-fluorotoluene;2-methyl-5-fluorobenzonitrile;5-Fluoro-2-methylben;2-Cyano-4-fluorotoluene, 5-Fluoro-o-tolunitrile
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CAS No:
Characteristics
23.8
2.1
yellow low melting solid
1.1±0.1 g/cm3
43-45 °C(lit.)
19.5ºC at 760mmHg
175 °F
1.508
Room temperature.
Safety Information
III
6.1
3276
3
37/38-41
26-39
Xi,T
Toxic
P261-P280-P305 + P351 + P338
H315-H318-H335
|Danger|H302 (13.04%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 46 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
5-Fluoro-2-methylbenzonitrile Use and Manufacturing
General procedure: A mixture of aldoximes (1 mmol) and imidazole (3 mmol) in anhydrous DCM (10-15 mL) was charged into an oven-dried round-bottom flask under nitrogen and the reaction mixture was stirred at r.t. for 20 min, after which triflic anhydride (0.4-1.0 mmol) was added dropwise via syringe under nitrogen, and the reaction mixture was allowed to stir at r.t. for a specific time (Table 1). Progress of the reaction was monitored by TLC and/or by GC-MS. Upon completion, the reaction mixture was quenched with dilute NaHCON2 was passed through a mixture of N2 was passed through a mixture of 2-(Bromomethyl-5-fluorobenzonitrile. N2 was passed through a mixture of 2-(Bromomethyl)-5-fluorobenzonitrile. N2 was passed through a mixture of 5- fluoro-2-methylbenzonitrile (28.51 g, 211 mmol), NBS (41.31 g, 232 mmol) and AIBN (2.5 g, 15 mmol) in CCl4 (845 mL) for 10 min after which the reaction was heated at reflux for 8 h. After standing at room temperature overnight, the reaction mixture was filtered and the filter cake washed with CCl4 (500 mL). The combined filtrate was evaporated to give a yellow oil. Flash chromatography (SiO2) using 5- 25% ethyl acetate/Hexanes as eluent afforded the title compound (29.74 g, 66% yield) as a pale yellow oil. 1H NMR (500 MHz, CDCl3) 6: 7.55 (IH, dd, J = 8.6, 5.2 Hz)5 7.37 (IH, dd, J = 7.9, 2.8 Hz), 7.32-7.28 (IH, m), 4.61 (2H, s).To a solution of 5-fluoro-2- methylbenzonitrile (5a)(5 g, 37 mmol) in CC14 (50 mL) was added NBS (7.3 g, 41 mmol) and AIBN (0.6 g, 3.7 mmol). The resulting mixture was heated at 80 C overnight. The reaction mixture concentrated under reduced pressure and the residue was purified by silica gel chromatography (petroleum ether/ethylacetate = 5: 1) to afford the compound as a white solid (2.8 g, 35 %). MS m/z 214.96[M+H]+.A solution of 1 (3.4 g, 25.2 mmol), NBS (4.63 g, 26 mmol) and 100 mg AIBN was refluxed for 2 hours under nitrogen. After cooling to room temperature, the solvent was removed and the residue was purified by column chromatography. 1H NMR (400 MHz, CDCl3): 7.51-7.59 (m, 1H), 7.26-7.39 (m, 2H), 4.61 (s, 2H).Step A. 2-(Bromomethyl)-5-fluorobenzonitrile A solution of To a nitromethane (0.1 mL) solution of
Computed Properties
Molecular Weight:135.14
XLogP3:2.1
Hydrogen Bond Acceptor Count:2
Exact Mass:135.048427358
Monoisotopic Mass:135.048427358
Topological Polar Surface Area:23.8
Heavy Atom Count:10
Complexity:158
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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