acetophenone

Also known as benzoyl methanide, 1-phenylethanone, methylphenylketone, phenylmethylketone, methyl phenyl ketone, phenyl methyl ketone, acetylbenzene, benzoylmethane

Acetophenone is the organic compound with the formula C6H5C(O)CH3. It is the simplest aromatic ketone. This colorless, viscous liquid is a precursor to useful resins and fragrances.

In the Vinony graph

Within Vinony's link graph, acetophenone is referenced by 699 other articles, and connects out to benzodiazepine drug, alphenal and apple.

Vinony files it under Acetophenones, Acetyl compounds and Chembox having GHS data.

Its subject is documented across 39 Wikipedia language editions.

Chemical data

Formula: C8H8O
Molecular weight: 120.15 g/mol
IUPAC name: 1-phenylethanone
SMILES: CC(=O)C1=CC=CC=C1
InChIKey: KWOLFJPFCHCOCG-UHFFFAOYSA-N
XLogP: 1.6
Polar surface area: 17.1 Å²
H-bond donors: 0
H-bond acceptors: 1
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Has part: benzoyl
Mass: 120.058
Image: Ацетофенон.jpg
Autonomy: 535

Show 23 more facts

Commons category: Acetophenone
chemical formula: C₈H₈O
canonical SMILES: CC(=O)C1=CC=CC=C1
crystal system: monoclinic crystal system
subject has role: excipient
MCN code: 2914.39.10
safety classification and labelling: Regulation (EC) No. 1272/2008
melting point: 20
boiling point: 202
density: 1.03
dynamic viscosity: 0.634
refractive index: 1.5372
partition coefficient water/octanol: 1.63
solubility: 6.9
phase point: critical point
surface tension: 33.27
vapor pressure: 2.9
electric dipole moment: 3.02
flash point: 77
lower flammable limit: 55
has characteristic: bitterness
ionization energy: 9.29
different from: benzophenone

Sources (3)

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~4 min read

Encyclopedic overview

11 sections

Contents

Production
Uses
Precursor to resins
Niche uses
Laboratory reagent
Drugs
Natural occurrence
Pharmacology
Toxicity
References
External links

Acetophenone is the organic compound with the formula C6H5C(O)CH3. It is the simplest aromatic ketone. This colorless, viscous liquid is a precursor to useful resins and fragrances.

==Production== Acetophenone is formed as a byproduct of the cumene process, the industrial route for the synthesis of phenol and acetone. In the Hock rearrangement of isopropylbenzene hydroperoxide, migration of a methyl group rather than the phenyl group gives acetophenone and methanol as a result of an alternate rearrangement of the intermediate:

Excerpted from Wikipedia’s “acetophenone” article, available under the CC BY-SA 4.0 licence.