Acetanisole

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Acetanisole
Acetanisole V.1.svg
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.560 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C9H10O2/c1-7(10)8-3-5-9(11-2)6-4-8/h3-6H,1-2H3
  • CC(=O)C1=CC=C(C=C1)OC
Properties
C9H10O2
Molar mass 150.177 g·mol−1
AppearanceWhite to pale yellow crystals [1]
Density 1.094 g/cm3
Melting point 38.2 °C (100.8 °F; 311.3 K) [2]
Boiling point 254 °C (489 °F; 527 K) [2]
2470 mg/L [1]
Hazards
Flash point 138 °C (280 °F) [3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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. [3] 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.

Contents

Acetanisole is found naturally in castoreum, the glandular secretion of the beaver. [1]

Preparation

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

Acetanisol Synthesis.svg

Application

It is used as a cigarette additive, [4] a fragrance, [1] and a flavoring in food. [5]

Reactions

4-Methoxyacetophenone is a standard substrate or product of much research, such as transfer hydrogenation [6] and directed arylations. [7]

References

  1. 1 2 3 4 Para-Acetanisole, The Good Scents Company
  2. 1 2 4'-Methoxyacetophenone from PubChem
  3. 1 2 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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