Phenol, 3-aMino-2-broMo- Chemical Properties

Boiling point:

262.2±20.0 °C(Predicted)

Density 

1.768±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

8.48±0.10(Predicted)

Appearance

White to off-white Solid

Safety Information

HS Code 

2922290090

Phenol, 3-aMino-2-broMo- Usage And Synthesis

Synthesis

General procedure for the synthesis of 3-amino-2-bromophenol from 2-bromo-3-nitrophenol: 2-bromo-3-nitrophenol (3.35 g, 15.4 mmol), acetic acid (35 mL), and powdered iron (4.5 g, 77.2 mmol) were mixed in ethanol (50 mL), and the reaction was stirred overnight under reflux conditions. Upon completion of the reaction, the mixture was diluted with 100 mL of water and neutralized with potassium carbonate. Subsequently, extraction was carried out with dichloromethane (DCM). The organic phase was dried with anhydrous sodium sulfate and concentrated under vacuum to give a brown oily crude product. The crude product was purified by column chromatography by dry loading onto a silica gel column using a 0-50% ethyl acetate/isohexane gradient elution. The target fraction was collected and concentrated in vacuum to give 3-amino-2-bromophenol (1.27 g, 6.75 mmol, 43.9% yield) as a light yellow solid. [00409] 1H NMR (DMSO-d6): δ 7.02 (t, J = 8.0 Hz, 1H), 6.45 (dd, J = 1.6 and 8.0 Hz, 1H), 6.38 (dd, J = 1.6 and 8.0 Hz, 1H), 5.44 (br s, 1H), 4.89 (br s, 2H).

References

[1] Journal of Organic Chemistry, 1988, vol. 53, # 6, p. 1170 - 1176
[2] Chemistry - A European Journal, 2017, vol. 23, # 42, p. 9996 - 10000
[3] Patent: WO2015/79251, 2015, A1. Location in patent: Paragraph 00408; 00409