6-BROMO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE Chemical Properties

Boiling point:

116-118 °C(Press: 4 Torr)

Density 

1.514±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

4.28±0.20(Predicted)

Appearance

Off-white to pale purple Solid

Safety Information

Hazard Codes 

T

Risk Statements 

25-51/53-36/37/38

Safety Statements 

45-61-36-26

RIDADR 

UN2811

HS Code 

29339900

6-BROMO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE Usage And Synthesis

Chemical Properties

White to off-white to light brown powder

Synthesis

Step 1: Synthesis of 6-bromo-2,3-dihydro-1H-indole To a mixed solution of 6-bromo-1H-indole (11.0 g, 56.1 mmol) in dichloromethane (180 mL) and trifluoroacetic acid (60 mL) was added triethylsilane (22.6 mL, 2.5 equiv). The reaction mixture was stirred at room temperature for 16 hours. Subsequently, additional dichloromethane (180 mL), concentrated ammonium hydroxide solution (about 50 mL) and water (200 mL) were added. The mixture was extracted with dichloromethane, the organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was redissolved in a solvent mixture of ether and hexane (1:1, 100 mL), and a dioxane solution of 4N HCl (14 mL) was slowly added, and a precipitate was immediately observed to form. The precipitate was collected by filtration and the resulting solid was treated with saturated sodium bicarbonate solution. The mixture was again extracted with dichloromethane, the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 6-bromo-2,3-dihydro-1H-indole as a brown oil (ca. 10.0 g), which was used directly in the subsequent reaction without further purification.LC-MS analysis: m/z 195.9/197.9 [M-H]+, retention time 0.98 min.

References

[1] ChemMedChem, 2016, vol. 11, # 23, p. 2607 - 2620
[2] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 5, p. 373 - 377
[3] Patent: WO2016/25932, 2016, A1. Location in patent: Page/Page column 144
[4] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 2425 - 2437
[5] Organic and Biomolecular Chemistry, 2018, vol. 16, # 32, p. 5889 - 5898

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