8-bromo-1,2,3,4-tetrahydroisoquinoline Chemical Properties

Boiling point:

294℃

Density 

1.428

Flash point:

132℃

storage temp. 

2-8°C(protect from light)

pka

8.88±0.20(Predicted)

Appearance

Off-white to yellow Solid-liquid mixture

InChI

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

InChIKey

KHWGHUZYXQPIKA-UHFFFAOYSA-N

SMILES

C1C2=C(C=CC=C2Br)CCN1

8-bromo-1,2,3,4-tetrahydroisoquinoline Usage And Synthesis

Uses

8-Bromo-1,2,3,4-tetrahydroisoquinoline is a useful intermediate for organic synthesis.

Uses

8-Bromo-1,2,3,4-tetrahydroisoquinoline is a useful intermediate for organic synthesis.

Synthesis

To a solvent mixture of methanol (20 mL) and saturated aqueous sodium carbonate (20 mL) was added 1-(6-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroacetophenone mixed with 1-(8-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone (3 g, 9.7 mmol). The reaction mixture was heated to reflux overnight and subsequently concentrated. The residue was extracted with dichloromethane, the organic layers were combined, washed sequentially with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The crude product was purified by silica gel column chromatography (230-400 mesh) with 0-2% methanol/chloroform solution as eluent to give 8-bromo-1,2,3,4-tetrahydroisoquinoline (first fraction, colorless viscous oil, 0.45 g, 22% yield) and 6-bromo-1,2,3,4-tetrahydroisoquinoline (second fraction, white solid, 1.0 g, 48% yield) sequentially. Mass spectrum (MS) m/z: 211.9 [M + H]+.

References

[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

8-bromo-1,2,3,4-tetrahydroisoquinoline(75416-51-2)Related Product Information

• 8-BROMO-1,2,3,4-TETRAHYDROISOQUINOLINE HYDROCHLORIDE
• 8-Bromo-1,2,3,4-tetrahydroquinoline hydrochloride
• Tetrahydropyran
• 8-broMo-4,4-diMethyl-1,2,3,4-tetrahydroquinoline
• 8-BROMO-1,3,4,5-TETRAHYDROBENZO[B]AZEPINE-2-ONE
• 8-bromo-1,2,3,4-tetrahydroquinoline
• 8-Iodo-naphthalen-1-ylamine
• 8-FLUORO-1,2,3,4-TETRAHYDROISOQUINOLINE HCL
• 1,2,3,4-TETRAHYDRO-ISOQUINOLIN-8-OL
• 1-Amino-8-chloronaphthalene
• 8-CHLORO-[1,7]NAPHTHYRIDINE
• 8-Fluoroisoquinoline
• IMIDAZO[1,2-A]PYRIDINE-8-CARBOXYLIC ACID
• 8-FLUORO-3,4-DIHYDRONAPHTHALEN-1(2H)-ONE
• 8-amino-1,2,3,4-tetrahydronaphthalen-1-one
• 1,2,3,4-TETRAHYDROISOQUINOLINE
• 5,6,7,8-TETRAHYDROISOQUINOLINE
• 8-bromo-1,2,3,4-tetrahydroisoquinoline