2-Acetylfuran has a low melting point and a high boiling point. 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.
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
Cefuroxime, sold under the brand name Zinacef among others, is a second-generation cephalosporin antibiotic used to treat and prevent a number of bacterial infections. These include pneumonia, meningitis, otitis media, sepsis, urinary tract inf ...
.
Synthesis
2-Acetylfuran was prepared by Ashina in 1914 via the reaction of the methyl
Grignard reagent
Grignard reagents or Grignard compounds are chemical compounds with the general formula , where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromi ...
on
2-furonitrile
2-Furonitrile is a colorless derivative of furan possessing a nitrile group.
Synthesis
Industrial synthesis is based on the vapor phase ammoxidation of furfural with ammonia over bismuth molybdate catalyst at 440–480 °C.
Numerous labor ...
.
Modern industrial synthesis generally involves the
Friedel–Crafts acylation of
furan
Furan is a Heterocyclic compound, heterocyclic organic compound, consisting of a five-membered aromatic Ring (chemistry), ring with four carbon Atom, atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as f ...
with
acetic anhydride
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the chemical formula, formula . Commonly abbreviated , it is one the simplest organic acid anhydride, anhydrides of a carboxylic acid and is widely used in the production of c ...
.
Applications
Pharmaceuticals
A one-pot synthesis of an intermediate to the
HIV integrase
Retroviral integrase (IN) is an enzyme produced by a retrovirus (such as HIV) that integrates (forms covalent links between) its genetic information into that of the host cell it infects. Retroviral INs are not to be confused with phage inte ...
inhibitor S-1360 was based on the
Friedel-Crafts alkylation of 2-acetylfuran with 4-fluorobenzyl chloride using zinc chloride catalyst.
Reaction of 2-acetylfuran with aqueous
sodium nitrite
Sodium nitrite is an inorganic compound with the chemical formula . It is a white to slightly yellowish crystalline powder that is very soluble in water and is hygroscopic. From an industrial perspective, it is the most important nitrite sa ...
gave 2-furanyloxoacetic acid, an intermediate to
Cefuroxime
Cefuroxime, sold under the brand name Zinacef among others, is a second-generation cephalosporin antibiotic used to treat and prevent a number of bacterial infections. These include pneumonia, meningitis, otitis media, sepsis, urinary tract inf ...
, a second-generation cephalosporin antibiotic.
Artificial flavouring
This compound has a balsamic, caramellic, sweet, almond, nutty profile with recommended uses in bakery, chocolate, cocoa, coffee, nut and tomato products.
See also
*
Isomaltol
Isomaltol is a natural furan obtained by the enzymatic degradation of starch. It is also a flavor component in bread crust, produced by thermal degradation (caramelization) of sugars.''Principles of Food Chemistry'' (1999), John M. DeMan, pg 28 ...
- same core, with a hydroxy group in the 3-position
*
2-Furoic acid
References
{{DEFAULTSORT:Acetylfuran, 2-
2-Furyl compounds
Acetyl compounds