6-Bromo-1,2,3,4-tetrahydronaphthalen-2-amine Chemical Properties

Boiling point:

298.7±40.0 °C(Predicted)

Density 

1.413±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

10.02±0.20(Predicted)

Safety Information

HS Code 

2921490090

6-Bromo-1,2,3,4-tetrahydronaphthalen-2-amine Usage And Synthesis

Synthesis

General procedure: preparation of 6-bromo-1,2,3,4-tetrahydronaphthalen-2-amine. To a solution of methanol (100 mL) containing 6-bromo-3,4-dihydro-1H-2-naphthalenone (2 g, 8.89 mmol) and NH4OAc (5.52 g, 71.61 mmol), NaCNBH3 (0.67 g, 10.66 mmol) was added at room temperature. The reaction mixture was stirred at room temperature for 20 h. The solution was observed to turn yellow. After completion of the reaction, the reaction mixture was acidified with 2M HCl and stirred for 10 min, followed by evaporation to remove methanol. The mixture was extracted twice with dichloromethane (CH2Cl2). The aqueous layer was adjusted to pH 10 with 1.0 N NaOH and again extracted twice with dichloromethane (CH2Cl2). The organic layers were combined, dried over anhydrous MgSO4 and concentrated in vacuum to afford 1.31 g (65% yield) of the target product 6-bromo-1,2,3,4-tetrahydronaphthalen-2-amine as a yellow oil, which could be used in the subsequent reaction without further purification.LRMS: m/z 226.1 (M + H)+, 209 (M + H-NH3)+. Retention time: 3.84 min (Method B). 1H NMR (300 MHz, CD3OD) δ 7.27-7.35 (m, 8H), 7.05 (d, J = 8.4Hz, 4H), 3.56 (m, 1H), 3.17 (dd, J = 3.9,16.2Hz, 1H), 2.95 (m, 2H), 2.81 (dd, J = 9.9,16.2Hz, 1H), 2.19-2.29 (m, 1H), 1.79-1.92 (m, 1H).

References

[1] Patent: EP2202232, 2010, A1. Location in patent: Page/Page column 71
[2] Patent: WO2016/16162, 2016, A1. Location in patent: Page/Page column 21
[3] Patent: WO2016/33025, 2016, A1. Location in patent: Page/Page column 62-63
[4] Patent: WO2008/1160, 2008, A1. Location in patent: Page/Page column 21-23
[5] Patent: US2005/75324, 2005, A1. Location in patent: Page/Page column 9; 10

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