2-Acetylfuran

2-Acetylfuran
Names
	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
CAS Number	1192-62-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:59983;
ChemSpider	13849;
ECHA InfoCard	100.013.416
PubChem CID	14505;
UNII	Q5ZRP80K02 ;
CompTox Dashboard (EPA)	DTXSID0051601 ;
	InChI InChI=1S/C6H6O2/c1-5(7)6-3-2-4-8-6/h2-4H,1H3 Key: IEMMBWWQXVXBEU-UHFFFAOYSA-N; InChI=1/C6H6O2/c1-5(7)6-3-2-4-8-6/h2-4H,1H3 Key: IEMMBWWQXVXBEU-UHFFFAOYAG;
	SMILES CC(=O)C1=CC=CO1;
Properties
Chemical formula	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). Infobox references

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

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

Pharmaceuticals

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

This compound has a balsamic, caramellic, sweet, almond, nutty profile with recommended uses in bakery, chocolate, cocoa, coffee, nut and tomato products.^[7]

References

^ 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".

[1] 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.

[2] 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-3] 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.

[4] 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.

[5] 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.

[6] 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.

[7] "Online Compendium".

[1]

[2]

[3]

[4]

[5]

[6]

[7]