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278564

Sigma-Aldrich

4′-Hydroxyacetophenone

99%

Synonym(s):

4-Hydroxyphenylethanone, p-Acetophenol, p-Hydroxyphenyl methyl ketone, Piceol

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About This Item

Linear Formula:
HOC6H4COCH3
CAS Number:
99-93-4
Molecular Weight:
136.15
Beilstein:
774355
EC Number:
202-802-8
MDL number:
MFCD00002359
UNSPSC Code:
12352100
PubChem Substance ID:
24856821
NACRES:
NA.22

Assay

99%

form

solid

bp

147-148 °C/3 mmHg (lit.)

mp

109-111 °C (lit.)

solubility

95% ethanol: 5%, colorless to faintly yellow

SMILES string

CC(=O)c1ccc(O)cc1

InChI

1S/C8H8O2/c1-6(9)7-2-4-8(10)5-3-7/h2-5,10H,1H3

InChI key

TXFPEBPIARQUIG-UHFFFAOYSA-N

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General description

Molecular dynamics simulation study of the two known polymorphs of 4′-hydroxyacetophenone (form I, monoclinic; form II, orthorhombic) has been described.

Application

4′-Hydroxyacetophenone has been used as ketone component in the preparation of 1-aryl-3-phenethylamino-1-propanone hydrochlorides, potential cytotoxic agents, via Mannich reactions.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319,H412

Hazard Classifications

Aquatic Chronic 3 - Eye Irrit. 2

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 1

Flash Point(F)

330.8 °F

Flash Point(C)

166 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Colbie R Chinowsky et al.
Molecular biology of the cell, 31(25), 2803-2815 (2020-10-08)
Brush border microvilli enable functions that are critical for epithelial homeostasis, including solute uptake and host defense. However, the mechanisms that regulate the assembly and morphology of these protrusions are poorly understood. The parallel actin bundles that support microvilli have
Ebru Mete et al.
Molecules (Basel, Switzerland), 12(12), 2579-2588 (2008-02-09)
1-Aryl-3-phenethylamino-1-propanone hydrochlorides 1-10, which are potentialpotent cytotoxic agents, were synthesized via Mannich reactions using paraformaldehyde,phenethylamine hydrochloride as the amine component and acetophenone, 4'-methyl-, 4'-methoxy-, 4'-chloro-, 4'-fluoro-, 4'-bromo-, 2',4'-dichloro-, 4'-nitro-, 4'-hydroxyacetophenone or 2-acetylthiophene as the ketone component. Yields were in the87-98
Carlos E S Bernardes et al.
The journal of physical chemistry. B, 116(17), 5179-5184 (2012-04-12)
A molecular dynamics simulation study of the two known polymorphs of 4′-hydroxyacetophenone (HAP; form I, monoclinic; form II, orthorhombic) is described. The modeling of the lattice energetics was found to be particularly sensitive to the atomic point charge (APC) selection
Peng Zuo et al.
The Journal of organic chemistry, 70(22), 8661-8675 (2005-10-22)
[reaction; see text] Picosecond and nanosecond time-resolved resonance Raman (TR(3)) spectroscopy was employed to investigate the deprotonation/ionization reaction of p-hydroxyacetophenone (HA) after ultraviolet photolysis in water solution. The TR(3) spectra in conjunction with density functional theory (DFT) calculations were used
Mariëlle J H Moonen et al.
Journal of bacteriology, 190(15), 5190-5198 (2008-05-27)
The catabolism of 4-hydroxyacetophenone in Pseudomonas fluorescens ACB is known to proceed through the intermediate formation of hydroquinone. Here, we provide evidence that hydroquinone is further degraded through 4-hydroxymuconic semialdehyde and maleylacetate to beta-ketoadipate. The P. fluorescens ACB genes involved
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