7-BROMO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE Chemical Properties

Melting point:

32-35°C

Boiling point:

282.9±40.0 °C(Predicted)

Density 

1.428±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

form 

solid

pka

9.14±0.20(Predicted)

color 

White

Water Solubility 

Insoluble in water.

InChI

InChI=1S/C9H10BrN/c10-9-2-1-7-3-4-11-6-8(7)5-9/h1-2,5,11H,3-4,6H2

InChIKey

OYODEQFZAJVROF-UHFFFAOYSA-N

SMILES

C1C2=C(C=CC(Br)=C2)CCN1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933499090

7-BROMO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE Usage And Synthesis

Uses

7-Bromo-1,2,3,4-tetrahydroisoquinoline is used as a pharmaceutical intermediate.

Synthesis Reference(s)

The Journal of Organic Chemistry, 63, p. 4116, 1998 DOI: 10.1021/jo972184e

Synthesis

The general procedure for the synthesis of 7-bromo-1,2,3,4-tetrahydroisoquinoline from N-trifluoroacetyl-7-bromo-1,2,3,4-tetrahydroisoquinoline was as follows: 1-(7-bromo-3,4-dihydro-1H-isoquinolin-2-yl)-2,2,2-trifluoroacetophenone (14.3 g, 46.4 mmol) was added to a mixture of methanol (50 mL) and saturated sodium carbonate solution ( 50 mL) to a mixture of methanol (50 mL) and saturated sodium carbonate solution (50 mL). The reaction mixture was stirred at 60 °C for 1 hour. After completion of the reaction, the mixture was concentrated and the residue was extracted with ethyl acetate. The organic layers were combined, washed sequentially with water and brine, and then dried over anhydrous sodium sulfate. After evaporation of the solvent, the crude product was purified by column chromatography to afford the light yellow solid product 7-bromo-1,2,3,4-tetrahydroisoquinoline (8.4 g, 85% yield). Mass spectrometry analysis showed m/z 213.8 (M + 1).

References

[1] Patent: WO2008/76954, 2008, A2. Location in patent: Page/Page column 51
[2] Patent: US2008/81803, 2008, A1. Location in patent: Page/Page column 34-35

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