5-Chloromethylfurfural

5-Chloromethylfurfural is an organic compound with the formula C4H2O(CH2Cl)CHO. It consists of a furan substituted at the 2- and 5-positions with formyl (CHO) and chloromethyl (CH2Cl) groups. CMF, as it is called, is obtained by dehydration of fructose and other cellulose derivatives using hydrochloric acid. It is a colourless liquid.[1] It can be reduced to give 5-methylfurfural, and can be hydrolyzed to give hydroxymethylfurfural.

5-Chloromethylfurfural
Names
Preferred IUPAC name
5-(Chloromethyl)furan-2-carbaldehyde
Other names
5-(Chloromethyl)-2-furaldehyde
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.015.099 Edit this at Wikidata
UNII
  • c1cc(oc1CCl)C=O
Properties
C6H5ClO2
Molar mass 144.55 g·mol−1
Appearance Colourless liquid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Typical nitrile gloves do not protect against CMF. The compound, even when handled as a solid, can absorb through gloves and stain the skin a dark brown black color. The health implications of dermal CMF exposure are unclear; CMF should be handled with caution.

References

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  1. ^ I. J. Rinkes "5-Methylfurfural" Org. Synth. 1934, volume 14, 62. doi:10.15227/orgsyn.014.0062