2-HYDROXY-1-(4-NITROPHENYL)-1-ETHANONE Chemical Properties

Melting point:

140-143°C

Boiling point:

338.4±17.0 °C(Predicted)

Density 

1.390±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

12.42±0.10(Predicted)

form 

solid

InChI

InChI=1S/C8H7NO4/c10-5-8(11)6-1-3-7(4-2-6)9(12)13/h1-4,10H,5H2

InChIKey

DRGHCHSDUDQWHJ-UHFFFAOYSA-N

SMILES

C(=O)(C1=CC=C([N+]([O-])=O)C=C1)CO

Safety Information

HazardClass 

IRRITANT

2-HYDROXY-1-(4-NITROPHENYL)-1-ETHANONE Usage And Synthesis

Synthesis

Example 13A Synthesis of 2-hydroxy-1-(4-nitrophenyl)ethanone: 2-bromo-1-(4-nitrophenyl)ethanone (5 g, 20.5 mmol) and silver nitrate (5 g, 29.4 mmol) were dissolved in a solvent mixture of water (250 mL) and acetone (150 mL) and heated to reflux the reaction for 4 hours. After the reaction was completed, it was cooled to room temperature. The reaction mixture was filtered and the filtrate was extracted twice with dichloromethane. The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated. The concentrate was purified by silica gel fast column chromatography with 2:1 hexane/ethyl acetate as eluent to give 3.7 g (50% yield) of the target product 2-hydroxy-1-(4-nitrophenyl)ethanone. Thin layer chromatography (TLC) showed an Rf value of 0.4 (eluent ratio 1:1 hexane/ethyl acetate).

References

[1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 1, p. 74 - 80
[2] Journal of Organic Chemistry, 1989, vol. 54, # 18, p. 4473 - 4474
[3] European Journal of Medicinal Chemistry, 2013, vol. 67, p. 142 - 151
[4] Patent: US2003/225098, 2003, A1. Location in patent: Page 32
[5] Chemische Berichte, 1889, vol. 22, p. 203

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