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. 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
CAS Number	1623-88-7
3D model (JSmol)	Interactive image
ChemSpider	66800
ECHA InfoCard	100.015.099
PubChem CID	74191
UNII	MXU4UQA8XG Y
CompTox Dashboard (EPA)	DTXSID70167351
SMILES c1cc(oc1CCl)C=O
Properties
Chemical formula	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). Infobox references

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.