5-(Hydroxymethyl)furan-2-carbaldehyde

The title compound (HMF), C(6)H(6)O(3), is one of the products of acid-catalyzed dehydration of high-fructose corn syrup, and has been shown to be toxic to honey bees. The compound was crystallized at 276 K, and it was found that the two independent molecules in the asymmetric unit form an infinite O-H center dot center dot center dot O hydrogen-bonding chain that is linked into a three-dimensional network structure by weak intermolecular C-H center dot center dot center dot O contacts.