1-(4-BROMO-PHENYL)-CYCLOPROPYLAMINE
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1-(4-BROMO-PHENYL)-CYCLOPROPYLAMINE
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CAS No:
345965-54-0
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Formula:
C9H10BrN
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Chemical Name:
1-(4-BROMO-PHENYL)-CYCLOPROPYLAMINE
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Synonyms:
1-(4-BROMO-PHENYL)-CYCLOPROPYLAMINE;1-(4-BROMOPHENYL)CYCLOPROPANAMINE;Cyclopropanamine, 1-(4-bromophenyl)-;1-(4-bromophenyl)cyclopropan-1-amine
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CAS No:
Safety Information
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, 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.
1-(4-BROMO-PHENYL)-CYCLOPROPYLAMINE Use and Manufacturing
General procedure: Compound 3a (1.42g, 4.73mmol) in a 3.0N HCl solution in MeOH (10mL) was stirred at rt for 24h. The solvent was removed under reduced pressure. The resulting residue was then suspended in DCM and basified by a 2.0N solution of NaOH (20mL). The organic phases were then separated and combined and dried by anhydrous magnesium sulfate. The solvent was then removed and the residue was purified by column chromatography with pre-packed silica gel disposable column to afford the title compound 1a (1.12g, 99percent) as a brown foam.General procedure: General Procedure G: Cyclopropanation (0459) To a mixture of arylnitrile (1 equivalent) and Ti(Oi-Pr)4-bromobenzonitrile (3.00 g, 16.48 mmol) and titanium tetraisopropoxide (5.4 mL, 18.13 mmol) were dissolved in anhydrous ether (40 mL)Cooled to -78 ° C, A solution of ethylmagnesium bromide in diethyl ether (3M, 12 mL, 39.88 mmol) was added dropwise.After dripping, The reaction was continued for 10 minutes at this temperature, And then allowed to react at room temperature for 1 hour.A solution of boron trifluoride in ether (4.2 mL, 36.26 mmol) was added, After stirring for 1 hour, Then add 1N dilute hydrochloric acid and ether.Water phase collection, And basified with 10percent aqueous sodium hydroxide solution, Ethyl acetate extraction.The organic phase is dried, After filtration and concentration, Intermediate 8 (1.7 g) was obtained in 48percent yield.To a solution of To a stirred solution of 4-fluorobenzoic acid (290 mg, 2.070 mmol) in DMF (8 mL) were added HATU (905 mg, 2.380 mmol), l-(4-bromophenyl)cyclopropanamine (505 mg, 2.380 mmol) and TEA (0.87 mL, 6.24 mmol) at RT and the reaction was stirred RT for 16 h. Then the mixture was diluted with water (50 mL), extracted with EtOAc (30 mLx3), and the organic layers were collected, washed with brine, dried over Na^SO^ and filtered. After filtration, the filtrate was concentrated in vacuo. The residue was purified by flash silica gel chromatography to afford the title compound as a solid. MS (ESI) m/z: 333.9 [M+H+]
Computed Properties
Molecular Weight:212.09
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:210.99966
Monoisotopic Mass:210.99966
Topological Polar Surface Area:26
Heavy Atom Count:11
Complexity:146
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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1-(4-BROMO-PHENYL)-CYCLOPROPYLAMINE
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