2-Acetylfuran

{{Chembox

| ImageFile = 2-Acetylfuran.svg

| ImageSize = 150px

| PIN = 1-(Furan-2-yl)ethan-1-one

| OtherNames = 1-(Furan-2-yl)ethanone
1-(2-Furanyl)-ethanone
2-Acetylfuran
Acetyl furan
2-Furyl methyl ketone

|Section1={{Chembox Identifiers

| CASNo = 1192-62-7

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = Q5ZRP80K02

| PubChem = 14505

| ChemSpiderID = 13849

| ChEBI = 59983

| SMILES = CC(=O)C1=CC=CO1

| InChI = 1/C6H6O2/c1-5(7)6-3-2-4-8-6/h2-4H,1H3

| InChIKey = IEMMBWWQXVXBEU-UHFFFAOYAG

| StdInChI = 1S/C6H6O2/c1-5(7)6-3-2-4-8-6/h2-4H,1H3

| StdInChIKey = IEMMBWWQXVXBEU-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| C=6 | H=6 | O=2

| Appearance = Low melting solid

| Density = 1.0975 at 20 °C

| MeltingPtC = 30

| BoilingPtC = 168 to 169

| Solubility =

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|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

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2-Acetylfuran has a low melting point and a high boiling point.

{{cite journal

| author = Howard D. Hartough| title = Acylation of thiophene and furan by means of boron trifluoride. VII| journal = Journal of the American Chemical Society| volume = 70 | pages = 867| year = 1948| last2 = Kosak| first2 = Alvin I.| issue = 2|doi=10.1021/ja01182a510 }}

{{cite journal

| author = Walther Borsche| title = Cleavage of the furan ring by primary aromatic amines and hydrochloric acid| journal = Berichte der Deutschen Chemischen Gesellschaft B| volume = 71| pages = 957–66| year = 1938| last2 = Leditschke| first2 = Heinrich| last3 = Lange| first3 = Karl}} 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.{{cite journal | first1 = Y. |last1 = Asahina| title = Ethereal oil of Elsholtzia cristata Willdenow (Lablatae)| journal = Archiv der Pharmazie| volume = 252| pages =435–48| year = 1914 | last2 = Murayama| first2 = Y.| doi=10.1002/ardp.19142520609|s2cid = 94708979| url = https://zenodo.org/record/1424585}} 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.{{cite journal | author = Rong-geng Wang| title = Side chain of cefuroxime: (Z)-2-methoxyimino-2-(fury-2-yl)acetic acid ammonium salt| journal = Jingxi Yu Zhuanyong Huaxuepin| volume = 12 | issue = 17| pages = 10–11| year = 2004| last2 = Liu| first2 = Cheng-ping| last3 = Zhu| first3 = Kun-peng| last4 = Du| first4 = Hai-lin | last5 = Liu| first5 = Lie-yi }}

Synthesis

2-Acetylfuran was prepared by Ashina in 1914 via the reaction of the methyl Grignard reagent on 2-furonitrile.

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.

{{cite journal | author = Kenji Izumi| title = One-Step Synthesis of 5-(4-Fluorobenzyl)-2-furyl Methyl Ketone: A Key Intermediate of HIV-Integrase Inhibitor S-1360| journal = Organic Process Research & Development| volume = 11 | issue = 6| pages = 1059–1061| year = 2007| last2 = Kabaki| first2 = Mikio| last3 = Uenaka| first3 = Masaaki| last4 = Shimizu| first4 = Sumio| doi=10.1021/op700117q}}

Reaction of 2-acetylfuran with aqueous sodium nitrite gave 2-furanyloxoacetic acid, an intermediate to Cefuroxime, a second-generation cephalosporin antibiotic.

{{cite journal | author = Rui-min Lv| title = The research for the synthesis of 2-methoxyimino-2-furylacetic acid| journal = Shandong Huagong| volume = 34 | issue = 6| pages = 5–8| year = 2005| last2 = Zhang| first2 = Zhi-de| last3 = Zhang| first3 = Zhi-cheng}}

=Artificial flavouring=

This compound has a balsamic, caramellic, sweet, almond, nutty profile with recommended uses in bakery, chocolate, cocoa, coffee, nut and tomato products.{{cite web | url=http://lmrnaturals.iff.com/en/site-services/flavor-online-compendium-iframe#2-furyl-methyl-ketone | title=Online Compendium }}

See also

References

{{Reflist}}

{{DEFAULTSORT:Acetylfuran, 2-}}

Category:2-Furyl compounds

Category:Acetyl compounds