4-Amino-2-fluorobenzonitrile
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4-Amino-2-fluorobenzonitrile
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CAS No:
53312-80-4
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Formula:
C7H5FN2
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Chemical Name:
4-Amino-2-fluorobenzonitrile
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Synonyms:
Benzonitrile,4-amino-2-fluoro-;4-Amino-2-fluorobenzonitrile;2-Fluoro-4-aminobenzonitrile;4-Cyano-3-fluoroaniline
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CAS No:
Safety Information
IRRITANT
Xi
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
4-Amino-2-fluorobenzonitrile Use and Manufacturing
Step A. Preparation of 4-amino-2-fluorobenzonitrile [00175] The mixture of 2-fluoro-4-nitrobenzonitrile (8.31 g, 50 mmol) and tin (II) chloride dihydrate (56.4 g, 250 mmol) in 250 mL of EtOAc was stirred at 25 °C overnight. LCMS (78109-084) indicated the reaction was completed. 25 mL of sat. K2CO3 was added to the reaction. The resulting mixture was stirred at room temperature for 2h and was followed by addition of lOOg of solid KA mixture of 4-nitro-2-fluorobenzonitrile (1.83 g, 5 mmol) and iron (1.68 g, 6 mmol) in a mixture of acetic acid (40 ml) and ethyl acetate (40 ml) was refluxed for 2 hours. The solid was filtered off and the filtrate was washed with water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, concentrated and chromatographed (dichloromethane:acetone, 95:5) to yield 4- amino-2-fluorobenzonitrile (54a) (0.653 g, 4.8 mmol, 96percent).To 2-fluoro-4-nitrobenzonitrile (8.5 g, 51.2 mmol) was added 10percent palladium on carbon (0.5 g) and EtOAc (42.5 mL) and EtOH (170 mL) and the reaction was hydrogenated at 50 psi for 1 h. The reaction was filtered through Celite and the reaction mixture was concentrated to afford 6.7 g (96percent yield) as a light brown solid. LCMS m/z 135.1[M + H]Reference Example 114 General procedure for deprotection of tert-butylsulfinyl group: N-(4-cyano-3-fluorophenyl)-2-methylpropane-2-sulfinamide (240 mg, 1.0 mmol) in 1, 4-dioxane (4 ml) was added 4.0M HCl in dioxane (4ml) and stirred at room temperature for 15 min. Reaction mixture was diluted with water, basified with saturated NaHCO2, 4-Difluorobenzonitrile (2.78 g, 20 mmol) and 3, 4, 5-trimethoxybenzylamine (3.94 g, 20 mmol) are combined and heated at 140 C for 40 m.
Computed Properties
Molecular Weight:136.13
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:136.04367633
Monoisotopic Mass:136.04367633
Topological Polar Surface Area:49.8
Heavy Atom Count:10
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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