5-Amino-2-fluorophenol

5-Amino-2-fluorophenol Property

Melting point:

156-158℃

Boiling point:

255.3±20.0 °C(Predicted)

Density 

1.347±0.06 g/cm3(Predicted)

storage temp. 

2-8°C, protect from light, stored under nitrogen

form 

Solid

pka

8.76±0.10(Predicted)

color 

White to yellow

Safety

HazardClass 

IRRITANT

HS Code 

2922290090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

5-Amino-2-fluorophenol Chemical Properties,Usage,Production

Uses

5-Amino-2-fluorophenol is used as synthetic building block.

Synthesis

Example 9A Step 1: 4-Fluoro-3-methoxyaniline (2.0 g, 14.2 mmol) was dissolved in dichloromethane (20 mL) at 0 °C and a dichloromethane solution of 1.0 M boron tribromide (40 mL) was slowly added dropwise. The reaction mixture was stirred at 0 °C, followed by gradual warming to room temperature and continued stirring overnight. Upon completion of the reaction, the reaction was quenched by the addition of methanol, followed by removal of the solvent under reduced pressure. Water was added to the residue, which was alkalized with saturated sodium bicarbonate solution to pH neutral and then extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 5-amino-2-fluorophenol as a white solid (1.3 g, 73% yield). The product was characterized by 1H NMR (300 MHz, DMSO-d6): δ 9.26 (s, 1H), 6.81 (dd, 1H), 6.34 (dd, 1H), 6.04 (dd, 1H), 4.63 (br, 2H).

References

[1] Patent: WO2009/117080, 2009, A1. Location in patent: Page/Page column 171
[2] Patent: US2002/198194, 2002, A1
[3] Patent: WO2011/119704, 2011, A1. Location in patent: Page/Page column 45