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[ CAS No. 226942-29-6 ]

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2D
Chemical Structure| 226942-29-6
Chemical Structure| 226942-29-6
Structure of 226942-29-6 *Storage: {[proInfo.prStorage]}

Quality Control of [ 226942-29-6 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 226942-29-6 ]

SDS

Product Details of [ 226942-29-6 ]

CAS No. :226942-29-6MDL No. :MFCD07374370
Formula :C9H10BrNBoiling Point :283°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :212.09Pubchem ID :15885183
Synonyms :

Computed Properties of [ 226942-29-6 ]

TPSA : 12 H-Bond Acceptor Count : 1
XLogP3 : 2 H-Bond Donor Count : 1
SP3 : 0.33 Rotatable Bond Count : 0

Safety of [ 226942-29-6 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 226942-29-6 ]

  • Upstream synthesis route of [ 226942-29-6 ]
  • Downstream synthetic route of [ 226942-29-6 ]

[ 226942-29-6 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 252331-63-8 ]
  • [ 726136-49-8 ]
  • [ 226942-29-6 ]
  • [ 75416-51-2 ]
YieldReaction ConditionsOperation in experiment
22% With water; sodium carbonate In methanolHeating / reflux 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)
Reference: [1] Patent: WO2008/76954, 2008, A2. Location in patent: Page/Page column 50
[2] Patent: US2008/171754, 2008, A1. Location in patent: Page/Page column 101; 102
[3] Patent: WO2009/39134, 2009, A1. Location in patent: Page/Page column 179
[4] Patent: WO2006/65215, 2006, A1. Location in patent: Page/Page column 17; 24
[5] Patent: WO2006/65216, 2006, A1. Location in patent: Page/Page column 16; 24
  • 2
  • [ 34784-05-9 ]
  • [ 226942-29-6 ]
YieldReaction ConditionsOperation in experiment
67.2% at 10 - 35℃; for 1.50 h; NaBH4 (3.46 g, 91.51 mmol) was slowly added to a mixture of 6-bromoisoquinoline (4.76 g, 22.88 mmol) and acetic acid (90 mL) at room temperature, and the mixture was stirred at room temperature for 1.5 hr.
To the reaction mixture was added water, and the mixture was adjusted to pH 8 with 8N aqueous sodium hydroxide solution.
The mixture was extracted 3 times with ethyl acetate/THF mixed solution (3:1).
The organic layer was washed with water, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure.
The residue was purified by silica gel column chromatography (NH, solvent gradient; 20→90percent ethyl acetate/hexane) to give 6-bromo-1,2,3,4-tetrahydroisoquinoline (3.26 g, 15.37 mmol, 67.2percent) as a colorless oil.
1H NMR (300 MHz, CDCl3):δ 1.63(1H,s), 2.77(2H,t,J=6.0 Hz), 3.11(2H,t,J=5.9 Hz), 3.95(2H,s), 6.85-6.90(1H,m), 7.21-7.26(2H,m).
Reference: [1] Patent: EP3192791, 2017, A1. Location in patent: Paragraph 0593
[2] Patent: WO2013/80222, 2013, A1. Location in patent: Page/Page column 39
[3] Applied Catalysis A: General, 2018, vol. 560, p. 37 - 41
  • 3
  • [ 147497-32-3 ]
  • [ 226942-29-6 ]
Reference: [1] Patent: US5977134, 1999, A
[2] Patent: EP1724263, 2006, A1. Location in patent: Page/Page column 40
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