Hydroxymethylfurfural

Hydroxymethylfurfural

Names
IUPAC name 5-(hydroxymethyl)-2-furaldehyde
Identifiers
CAS Number	67-47-0 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:412516 Y
ChEMBL	ChEMBL185885 Y
ChemSpider	207215 Y
ECHA InfoCard	100.000.595
KEGG	C11101 Y
InChI InChI=1S/C6H6O3/c7-3-5-1-2-6(4-8)9-5/h1-3,8H,4H2 Y Key: NOEGNKMFWQHSLB-UHFFFAOYSA-N Y InChI=1/C6H6O3/c7-3-5-1-2-6(4-8)9-5/h1-3,8H,4H2 Key: NOEGNKMFWQHSLB-UHFFFAOYAB
SMILES c1cc(oc1CO)C=O
Properties
Chemical formula	C6H6O3
Molar mass	126.11 g/mol
Density	1.29 g/cm3
Melting point	30 to 34 °C (86 to 93 °F; 303 to 307 K)
Boiling point	114 to 116 °C (237 to 241 °F; 387 to 389 K) (1 mbar)
UV-vis (λmax)	282 nm
Related compounds
Related furan-2-carbaldehydes	Furfural Methoxymethylfurfural
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Methoxymethylfurfural

Hydroxymethylfurfural (HMF), also 5-(Hydroxymethyl)furfural, is an organic compound derived from dehydration of certain sugars. This yellow low-melting solid is highly water-soluble. The molecule consists of a furan ring, containing both aldehyde and alcohol functional groups. HMF has been identified in a wide variety of baked goods. HMF, which is derived from hexoses, is a potential "carbon-neutral" feedstock for fuels and chemicals.

Related to the production of furfural, HMF is produced from sugars. It arises via the dehydration of fructose. Treatment of fructose with acids followed by liquid-liquid extraction into organic solvents such as methyl isobutyl ketone. The conversion is affected by various additives such as DMSO, 2-butanol, and polyvinyl pyrrolidone, which minimize the formation of side product. Ionic liquids facilitate the conversion of fructose to HMF. When hexoses are hydrolyzed with hydrochloric acid, 5-chloromethylfurfural is produced instead of HMF.

In the image above are displayed in a series of chemical equilibria: fructopyranose 1, fructofuranose 2, two intermediate stages of dehydration (not isolated) 3,4 and finally HMF 5.