2-Acetylfuran
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| Names | |
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| Preferred IUPAC name
1-(Furan-2-yl)ethan-1-one | |
| Other names
1-(Furan-2-yl)ethanone
1-(2-Furanyl)-ethanone 2-Acetylfuran Acetyl furan 2-Furyl methyl ketone | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.013.416 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C6H6O2 | |
| Molar mass | 110.112 g·mol−1 |
| Appearance | Low melting solid |
| Density | 1.0975 at 20 °C |
| Melting point | 30 °C (86 °F; 303 K) |
| Boiling point | 168 to 169 °C (334 to 336 °F; 441 to 442 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Acetylfuran has a low melting point and a high boiling point.[1][2] The solid melts at 30 °C and has a density of 1.0975 g/ml at 20 °C, while the normal boiling point of the liquid is 168–169 °C.[3] 2-Acetylfuran is a useful intermediate in the synthesis of fine chemicals and pharmaceuticals, and is used in the production of the generic cephalophosphorin antibiotic cefuroxime.[4]
Synthesis
[edit]2-Acetylfuran was prepared by Ashina in 1914 via the reaction of the methyl Grignard reagent on 2-furonitrile.[3] Modern industrial synthesis generally involves the Friedel–Crafts acylation of furan with acetic anhydride.
Applications
[edit]Pharmaceuticals
[edit]A one-pot synthesis of an intermediate to the HIV integrase inhibitor S-1360 was based on the Friedel-Crafts alkylation of 2-acetylfuran with 4-fluorobenzyl chloride using zinc chloride catalyst.[5]
Reaction of 2-acetylfuran with aqueous sodium nitrite gave 2-furanyloxoacetic acid, an intermediate to Cefuroxime, a second-generation cephalosporin antibiotic.[6]
Artificial flavouring
[edit]This compound has a balsamic, caramellic, sweet, almond, nutty profile with recommended uses in bakery, chocolate, cocoa, coffee, nut and tomato products.[7]
See also
[edit]- Isomaltol - same core, with a hydroxy group in the 3-position
- 2-Furoic acid
References
[edit]- ^ Howard D. Hartough; Kosak, Alvin I. (1948). "Acylation of thiophene and furan by means of boron trifluoride. VII". Journal of the American Chemical Society. 70 (2): 867. doi:10.1021/ja01182a510.
- ^ Walther Borsche; Leditschke, Heinrich; Lange, Karl (1938). "Cleavage of the furan ring by primary aromatic amines and hydrochloric acid". Berichte der Deutschen Chemischen Gesellschaft B. 71: 957–66.
- ^ a b Asahina, Y.; Murayama, Y. (1914). "Ethereal oil of Elsholtzia cristata Willdenow (Lablatae)". Archiv der Pharmazie. 252: 435–48. doi:10.1002/ardp.19142520609. S2CID 94708979.
- ^ Rong-geng Wang; Liu, Cheng-ping; Zhu, Kun-peng; Du, Hai-lin; Liu, Lie-yi (2004). "Side chain of cefuroxime: (Z)-2-methoxyimino-2-(fury-2-yl)acetic acid ammonium salt". Jingxi Yu Zhuanyong Huaxuepin. 12 (17): 10–11.
- ^ Kenji Izumi; Kabaki, Mikio; Uenaka, Masaaki; Shimizu, Sumio (2007). "One-Step Synthesis of 5-(4-Fluorobenzyl)-2-furyl Methyl Ketone: A Key Intermediate of HIV-Integrase Inhibitor S-1360". Organic Process Research & Development. 11 (6): 1059–1061. doi:10.1021/op700117q.
- ^ Rui-min Lv; Zhang, Zhi-de; Zhang, Zhi-cheng (2005). "The research for the synthesis of 2-methoxyimino-2-furylacetic acid". Shandong Huagong. 34 (6): 5–8.
- ^ "Online Compendium".