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Acetanisole

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(Redirected from 4-methoxyacetophenone)
Acetanisole
Names
Preferred IUPAC name 1-(4-Methoxyphenyl)ethan-1-one
Other names 4-Acetylanisole; para-Acetanisole; 4-Methoxyacetophenone; Linarodin; Novatone; Vananote; Castoreum anisole; 4-Methoxyphenyl methyl ketone
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.560 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H10O2/c1-7(10)8-3-5-9(11-2)6-4-8/h3-6H,1-2H3
SMILES
  • CC(=O)C1=CC=C(C=C1)OC
Properties
Chemical formula C9H10O2
Molar mass 150.177 g·mol
Appearance White to pale yellow crystals
Density 1.094 g/cm
Melting point 38.2 °C (100.8 °F; 311.3 K)
Boiling point 254 °C (489 °F; 527 K)
Solubility in water 2470 mg/L
Hazards
Flash point 138 °C (280 °F)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Acetanisole is an aromatic chemical compound with an aroma described as sweet, fruity, nutty, and similar to vanilla. In addition acetanisole can sometimes smell like butter or caramel. Its chemical names are based on considering the structure as either an acetyl (methyl-ketone) analog of anisole. Other names It can also be seen as a methyl ether analog of acetophenone.

Acetanisole is found naturally in castoreum, the glandular secretion of the beaver.

Preparation

Acetanisole can be prepared synthetically by Friedel-Crafts acylation of anisole with acetyl chloride:

Application

It is used as a cigarette additive, a fragrance, and a flavoring in food.

Reactions

4-Methoxyacetophenone is a standard substrate or product of much research, such as transfer hydrogenation and directed arylations.

References

  1. ^ Para-Acetanisole, The Good Scents Company
  2. ^ 4'-Methoxyacetophenone from PubChem
  3. ^ Acetanisole at Sigma-Aldrich
  4. Tobacco Documents | Profiles | Additives | Acetanisole Archived April 11, 2008, at the Wayback Machine
  5. 21 CFR 172.515
  6. Noyori, Ryoji; Yamakawa, Masashi; Hashiguchi, Shohei (2001). "Metal−Ligand Bifunctional Catalysis: A Nonclassical Mechanism for Asymmetric Hydrogen Transfer between Alcohols and Carbonyl Compounds". The Journal of Organic Chemistry. 66 (24): 7931–7944. doi:10.1021/jo010721w. PMID 11722188.
  7. Palucki, Michael; Buchwald, Stephen L. (1997). "Palladium-Catalyzed α-Arylation of Ketones". Journal of the American Chemical Society. 119 (45): 11108–11109. doi:10.1021/ja972593s.
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