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Merck
CN

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:
Molecular Weight:
136.15
Beilstein:
774355
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level

Assay

99%

form

solid

bp

147-148 °C/3 mmHg (lit.)

mp

109-111 °C (lit.)

solubility

95% ethanol: 5%, colorless to faintly yellow

functional group

ketone

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

Signal Word

Warning

Hazard Statements

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

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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
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
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), 5199-5209 (2008-05-27)
Hydroquinone 1,2-dioxygenase (HQDO), an enzyme involved in the catabolism of 4-hydroxyacetophenone in Pseudomonas fluorescens ACB, was purified to apparent homogeneity. Ligandation with 4-hydroxybenzoate prevented the enzyme from irreversible inactivation. HQDO was activated by iron(II) ions and catalyzed the ring fission
Roumen Christov et al.
Natural product research, 20(6), 531-536 (2006-07-13)
The chemical composition of propolis from two regions in Canada was studied: Boreal forest and Pacific coastal forest that lay outside the area of distribution of Aigeiros poplars, the usual propolis source plants. In the sample from Victoria, p-hydroxyacetophenone, benzyl

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