6-Bromo-1,2,3,4-tetrahydroisoquinoline
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6-Bromo-1,2,3,4-tetrahydroisoquinoline
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CAS No:
226942-29-6
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Formula:
C9H10BrN
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Chemical Name:
6-Bromo-1,2,3,4-tetrahydroisoquinoline
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CAS No:
Safety Information
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
6-Bromo-1,2,3,4-tetrahydroisoquinoline Use and Manufacturing
To a solution of methanol (20 mL) and saturated sodium carbonate solution (20 mL) are added a mixture of l-(6-Bromo-3, 4-dihydro-lH-isoquinolin-2-yl)-2, 2, 2-trifluoro- ethanone and l-(8-bromo-3, 4-dihydro-lH-isoquinolin-2-yl)-2, 2, 2-trifluoro-ethanone (3 g, 9.7 mmol). The reaction mixture is refluxed overnight, concentrated and the residue is extracted with dichloromethane. The combined organic layers are washed with water and brine, dried over sodium sulfate and the solvent is evaporated. The crude product is purified by column chromatography (silica gel, 230-400 mesh) using 0-2percent methanol in chloroform as eluent to obtain 8-bromo-l, 2, 3, 4-tetrahydro-isoquinoline as colorless viscous oil (first fraction, 0.45 g, 22percent) and 6-Bromo-l, 2, 3, 4-tetrahydro-isoquinoline as white solid (second fraction, 1.0 g, 48percent). MS m/z 211.9 (M+l)NaBHGeneral procedure: To the solution of amine (2a-10a) (1mmol) in DCM (5mL), triethylamine (2mmol) was added followed by benzylsulfonyl chloride, 2-Phenylethanesulfonyl chloride, benzene sulfonyl chloride, benzoyl chloride or phenylacetyl chloride (1.5mmol), and the mixture was stirred overnight at room temperature. The reaction was filtered, concentrated and solved by EA (20mL), then washed with ethyl acetate (3×15mL). The organic was combined and was dried over Na2SO4. After filtration, the filtrate was removed in vacuo. The residue was purified by silica gel column chromatography to give 2b-12b, 16b-17b.A mixture of To a stirred solution of
Computed Properties
Molecular Weight:212.09
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:210.99966
Monoisotopic Mass:210.99966
Topological Polar Surface Area:12
Heavy Atom Count:11
Complexity:138
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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6-Bromo-1,2,3,4-tetrahydroisoquinoline
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