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466964

Sigma-Aldrich

4′-Fluoro-2′-hydroxyacetophenone

98%

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About This Item

Fórmula lineal:
FC6H3(OH)COCH3
Número de CAS:
1481-27-2
Peso molecular:
154.14
MDL number:
MFCD00143203
UNSPSC Code:
12352100
PubChem Substance ID:
24870373
NACRES:
NA.22

Quality Level

100

assay

98%

mp

31-35 °C (lit.)

SMILES string

CC(=O)c1ccc(F)cc1O

InChI

1S/C8H7FO2/c1-5(10)7-3-2-6(9)4-8(7)11/h2-4,11H,1H3

InChI key

HLTBTUXAMVOKIH-UHFFFAOYSA-N

General description

4′-Fluoro-2′-hydroxyacetophenone is a substituted acetophenone derivative. Biological Baeyer-Villiger oxidation of 4′-fluoro-2′-hydroxyacetophenone to 4-fluorocatechol by using whole cells of Pseudomonas fluorescens ACB has been reported. Its crystals belong to the monoclinic crystal system and space group P21/n.

Application

4′-Fluoro-2′-hydroxyacetophenone may be used in the preparation of series of 4′-fluoro-2′-hydroxychalcones, via aldol condensation with substituted aldehydes followed by cyclization with hydrazine hydrate.
Used recently in the preparation of medicinally active benzo[b]furans and thiophenes.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

210.2 °F - closed cup

flash_point_c

99 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Khaled R A Abdellatif et al.
Journal of enzyme inhibition and medicinal chemistry, 30(3), 484-491 (2014-09-10)
In an effort to develop safe and potent anti-inflammatory agents, a series of novel 4'-fluoro-2'-hydroxychalcones 5a-d and their dihydropyrazole derivatives 6a-d was prepared. It was synthesized via aldol condensation of 4'-fluoro-2'-hydroxyacetophenone with appropriately substituted aldehydes followed by cyclization with hydrazine
4'-Fluoro-2'-hydroxyacetophenone.
Rizal MR and Ng SW.
Acta Crystallographica Section E, Structure Reports Online, 64(5), o916-o916 (2008)
M J Moonen et al.
Journal of industrial microbiology & biotechnology, 26(1-2), 35-42 (2001-09-11)
The biological Baeyer-Villiger oxidation of acetophenones was studied by 19F nuclear magnetic resonance (NMR). The 19F NMR method was used to characterise the time-dependent conversion of various fluorinated acetophenones in either whole cells of Pseudomonas fluorescens ACB or in incubations
Journal of Heterocyclic Chemistry, 30, 445-445 (1993)

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