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.
![]() | |
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 |
PubChem CID
|
|
UNII | |
CompTox Dashboard (EPA)
|
|
| |
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
edit- ^ I. J. Rinkes "5-Methylfurfural" Org. Synth. 1934, volume 14, 62. doi:10.15227/orgsyn.014.0062