2-AMINO-5-FLUOROPHENOL Chemical Properties

Melting point:

38°C

Boiling point:

246.1±25.0 °C(Predicted)

Density 

1.347±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMSO, Methanol

pka

8.76±0.10(Predicted)

form 

Solid

color 

Dark Beige

Water Solubility 

Slightly soluble in water.

Sensitive 

Air Sensitive

InChI

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

InChIKey

IIDUNAVOCYMUFB-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

53981-24-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

29089990

2-AMINO-5-FLUOROPHENOL Usage And Synthesis

Chemical Properties

Dark Beige Solid

Uses

2-Amino-5-fluorophenol is a fluoroaniline metabolite. 2-Amino-5-fluorophenol is used as organic intermediate. To synthesize the intermediate (2-amino-5-fluorophenol-N, N, O-triacetic acid trimethyl ester) of indicator which used in the determination Mg2+ by NMR, three feasible reactions were experimentally carried out, such as alkaline hydrolysis, catalytic hydrogenation and esterification.

Synthesis

The general procedure for the synthesis of 2-amino-5-fluorophenol from 5-fluoro-2-nitrophenol is as follows: 5-fluoro-2-nitrophenol (2.50 g, 15.9 mmol, commercially available from e.g., Aldrich) was dissolved in ethanol (50 ml), and 10% palladium-carbon catalyst (980 mg) was added for the hydrogenation reaction, which lasted for 1.5 hours. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated. The solid residue obtained was dissolved in ether, followed by addition of an equal volume of cyclohexane. The ether was removed by vacuum distillation at room temperature to give a light gray solid product. The product was filtered and washed with cyclohexane to give 2-amino-5-fluorophenol (1.90 g, 94% yield). Elemental analysis measured values: C, 56.4; H, 4.8; N, 10.9. theoretical values (C6H6FNO): C, 56.7; H, 4.8; N, 11.0%.

References

[1] Journal of Medicinal Chemistry, 2015, vol. 58, # 24, p. 9742 - 9753
[2] Patent: WO2010/94643, 2010, A1. Location in patent: Page/Page column 46
[3] Patent: US5238908, 1993, A
[4] Patent: US5393735, 1995, A
[5] Chemistry - A European Journal, 2011, vol. 17, # 33, p. 9076 - 9082

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