2-AMINO-4-FLUOROPHENOL Chemical Properties

Melting point:

130-135 °C

Boiling point:

252.9±25.0 °C(Predicted)

Density 

1.347±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

9.77±0.18(Predicted)

color 

Light yellow to Brown

InChI

InChI=1S/C6H6FNO/c7-4-1-2-6(9)5(8)3-4/h1-3,9H,8H2

InChIKey

ULDFRPKVIZMKJG-UHFFFAOYSA-N

SMILES

C1(O)=CC=C(F)C=C1N

CAS DataBase Reference

399-97-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38-22

Safety Statements 

26-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29222990

2-AMINO-4-FLUOROPHENOL Usage And Synthesis

Application

2-Amino-4-fluorophenol has wide applications in drug synthesis, serving as a synthetic intermediate for certain drugs. Furthermore, it possesses antibacterial and anti-inflammatory properties, making it useful in treating some infectious and inflammatory diseases.

Chemical Properties

White to brown solid

Synthesis

The general procedure for the synthesis of 2-amino-4-fluorophenol from 2-nitro-4-fluorophenol was as follows: tin(II) chloride (12.1 g, 63.6 mmol) was added to a solution of 4-fluoro-2-nitrophenol (2.00 g, 12.7 mmol) in ethanol (45 mL). The reaction mixture was heated to 70 °C and maintained at this temperature for 2 hours. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently poured into ice water (~200 mL). After the mixture was warmed to room temperature, the pH was adjusted with 2N NaOH aqueous solution to about 9. The reaction mixture was filtered and the filtrate was extracted with ethyl acetate (3×). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and the organic phase was concentrated under reduced pressure. 1.21 g (75% yield) of 2-amino-4-fluorophenol was finally obtained.Results of LC-MS analysis: retention time (RT) = 4.48 min, [M + H]+ = 128.0.

References

[1] Patent: EP1346982, 2003, A1
[2] Inorganic Chemistry, 2010, vol. 49, # 23, p. 11106 - 11117
[3] Patent: WO2007/146066, 2007, A2. Location in patent: Page/Page column 80
[4] Journal of Organic Chemistry, 1951, vol. 16, p. 1345,1348
[5] J. Gen. Chem. USSR (Engl. Transl.), 1975, vol. 45, p. 2372 - 2379

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