5-Methylfurfural

5-Methylfurfural
Names
	IUPAC name 5-Methylfuran-2-carbaldehyde
	Other names 5-Methyl-2-furaldehyde; 2-Furancarboxaldehyde, 5-methyl-;
Identifiers
CAS Number	620-02-0;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:2091;
ChEMBL	ChEMBL2230304;
ChemSpider	11600;
ECHA InfoCard	100.009.658
EC Number	210-622-6;
KEGG	C11115;
PubChem CID	12097;
CompTox Dashboard (EPA)	DTXSID1060714 ;
	InChI InChI=1S/C6H6O2/c1-5-2-3-6(4-7)8-5/h2-4H,1H3 Key: OUDFNZMQXZILJD-UHFFFAOYSA-N;
	SMILES CC1=CC=C(O1)C=O;
Properties
Chemical formula	C6H6O2
Molar mass	110.112 g·mol−1
Density	1.098-1.108 g/mL (20 °C)
Boiling point	187 °C (369 °F; 460 K)
Solubility in water	3.3 g/100mL
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

5-Methylfurfural is an organic compound with the formula C₆H₆O₂. An aldehyde that is derived through various extractions and reductions from cellulose products,^[5]^[6] it has applications as a synthetic intermediate^[7] relevant to the fields of medicine, agriculture and cosmetics.^[8] It is a food additive, and has FEMA number 270s and JECFA number 745.^[2] Reduction of 5-methylfurfural gives the product 5-methylfurfuryl alcohol.^[9]

Synthesis

The synthesis of 5-methylfurfural has been documented from as early as 1891. It was originally synthesized from rhamnose, but can be produced from the dehydration of sucrose and other cellulose products.^[5] Several synthetic pathways have been proposed from 5-hydroxymethylfurfural.^[7]^[10] The compound has been produced in the 21st century using the historical precursor of rhamnose with the aim to use it as a precursor to biogasoline.^[11]^[8]

References

^ "2-Furancarboxaldehyde, 5-methyl-". NIST Chemistry WebBook, SRD 69. 2023.
^ ^a ^b "Online Edition: "Specifications for Flavourings"". Food and Agriculture Organization of the United Nations. 2002. Retrieved June 25, 2024.
^ ^a ^b Zeitsch, Karl J., ed. (2000). "P. Properties of 5-methyl furfural". the chemistry and technology of furfural and its many by-products. Sugar Series. Vol. 13. Elsevier. p. 254. doi:10.1016/S0167-7675(00)80049-4. ISBN 978-0-444-50351-0. ISSN 0167-7675.
^ "5-Methylfurfural". pubchem.ncbi.nlm.nih.gov.
^ ^a ^b "5-METHYLFURFURAL". Organic Syntheses. 14: 62. 1934. doi:10.15227/orgsyn.014.0062.
^ Moe, Størker T.; Marcotullio, Gianluca; Opedal, Mihaela Tanase; Brusletto, Rune (December 2022). "Formation of 5-methylfurfural and 2-acetylfuran from lignocellulosic biomass and by Cr3+-catalyzed dehydration of 6-deoxyhexoses". Carbohydrate Research. 522: 108672. doi:10.1016/j.carres.2022.108672. hdl:11250/3055856. PMID 36183617.
^ ^a ^b Li, Shaopeng; Dong, Minghua; Yang, Junjuan; Cheng, Xiaomeng; Shen, Xiaojun; Liu, Shulin; Wang, Zhi-Qiang; Gong, Xue-Qing; Liu, Huizhen; Han, Buxing (January 26, 2021). "Selective hydrogenation of 5-(hydroxymethyl)furfural to 5-methylfurfural over single atomic metals anchored on Nb2O5". Nature Communications. 12 (1): 584. doi:10.1038/s41467-020-20878-7. ISSN 2041-1723. PMC 7838200. PMID 33500400.
^ ^a ^b Peng, Yang; Li, Xianghua; Gao, Tian; Li, Teng; Yang, Weiran (2019). "Preparation of 5-methylfurfural from starch in one step by iodide mediated metal-free hydrogenolysis". Green Chemistry. 21 (15): 4169–4177. doi:10.1039/C9GC01645G. ISSN 1463-9262.
^ Spillman, Philip J.; Pollnitz, Alan P.; Liacopoulos, Dimitra; Pardon, Kevin H.; Sefton, Mark A. (1998-02-01). "Formation and Degradation of Furfuryl Alcohol, 5-Methylfurfuryl Alcohol, Vanillyl Alcohol, and Their Ethyl Ethers in Barrel-Aged Wines". Journal of Agricultural and Food Chemistry. 46 (2): 657–663. doi:10.1021/jf970559r. ISSN 0021-8561. PMID 10554294.
^
- Sun, Guohan; An, Jiahuan; Hu, Hong; Li, Changzhi; Zuo, Songlin; Xia, Haian (2019). "Green catalytic synthesis of 5-methylfurfural by selective hydrogenolysis of 5-hydroxymethylfurfural over size-controlled Pd nanoparticle catalysts". Catalysis Science & Technology. 9 (5): 1238–1244. doi:10.1039/C9CY00039A. ISSN 2044-4753.
- Dong, Lin; Morales-Vidal, Jordi; Mu, Lili; Li, Licheng; López, Núria; Pérez-Ramírez, Javier; Chen, Zupeng (October 2023). "Selective hydrogenolysis of 5-hydroxymethylfurfural to 5-methylfurfural over Au/TiO2". Applied Catalysis B: Environmental. 335: 122893. doi:10.1016/j.apcatb.2023.122893.
^ Feng, Yunchao; Li, Zheng; Long, Sishi; Sun, Yong; Tang, Xing; Zeng, Xianhai; Lin, Lu (2020). "Direct conversion of biomass derived l -rhamnose to 5-methylfurfural in water in high yield". Green Chemistry. 22 (18): 5984–5988. doi:10.1039/D0GC02105A. ISSN 1463-9262.

[NISTWebbook-1] "2-Furancarboxaldehyde, 5-methyl-". NIST Chemistry WebBook, SRD 69. 2023.

[FAO-2] "Online Edition: "Specifications for Flavourings"". Food and Agriculture Organization of the United Nations. 2002. Retrieved June 25, 2024.

[Zeitsch-3] Zeitsch, Karl J., ed. (2000). "P. Properties of 5-methyl furfural". the chemistry and technology of furfural and its many by-products. Sugar Series. Vol. 13. Elsevier. p. 254. doi:10.1016/S0167-7675(00)80049-4. ISBN 978-0-444-50351-0. ISSN 0167-7675.

[4] "5-Methylfurfural". pubchem.ncbi.nlm.nih.gov.

[:0-5] "5-METHYLFURFURAL". Organic Syntheses. 14: 62. 1934. doi:10.15227/orgsyn.014.0062.

[6] Moe, Størker T.; Marcotullio, Gianluca; Opedal, Mihaela Tanase; Brusletto, Rune (December 2022). "Formation of 5-methylfurfural and 2-acetylfuran from lignocellulosic biomass and by Cr3+-catalyzed dehydration of 6-deoxyhexoses". Carbohydrate Research. 522: 108672. doi:10.1016/j.carres.2022.108672. hdl:11250/3055856. PMID 36183617.

[:1-7] Li, Shaopeng; Dong, Minghua; Yang, Junjuan; Cheng, Xiaomeng; Shen, Xiaojun; Liu, Shulin; Wang, Zhi-Qiang; Gong, Xue-Qing; Liu, Huizhen; Han, Buxing (January 26, 2021). "Selective hydrogenation of 5-(hydroxymethyl)furfural to 5-methylfurfural over single atomic metals anchored on Nb2O5". Nature Communications. 12 (1): 584. doi:10.1038/s41467-020-20878-7. ISSN 2041-1723. PMC 7838200. PMID 33500400.

[:2-8] Peng, Yang; Li, Xianghua; Gao, Tian; Li, Teng; Yang, Weiran (2019). "Preparation of 5-methylfurfural from starch in one step by iodide mediated metal-free hydrogenolysis". Green Chemistry. 21 (15): 4169–4177. doi:10.1039/C9GC01645G. ISSN 1463-9262.

[SpillmanA-9] Spillman, Philip J.; Pollnitz, Alan P.; Liacopoulos, Dimitra; Pardon, Kevin H.; Sefton, Mark A. (1998-02-01). "Formation and Degradation of Furfuryl Alcohol, 5-Methylfurfuryl Alcohol, Vanillyl Alcohol, and Their Ethyl Ethers in Barrel-Aged Wines". Journal of Agricultural and Food Chemistry. 46 (2): 657–663. doi:10.1021/jf970559r. ISSN 0021-8561. PMID 10554294.

[10] 
Sun, Guohan; An, Jiahuan; Hu, Hong; Li, Changzhi; Zuo, Songlin; Xia, Haian (2019). "Green catalytic synthesis of 5-methylfurfural by selective hydrogenolysis of 5-hydroxymethylfurfural over size-controlled Pd nanoparticle catalysts". Catalysis Science & Technology. 9 (5): 1238–1244. doi:10.1039/C9CY00039A. ISSN 2044-4753.
Dong, Lin; Morales-Vidal, Jordi; Mu, Lili; Li, Licheng; López, Núria; Pérez-Ramírez, Javier; Chen, Zupeng (October 2023). "Selective hydrogenolysis of 5-hydroxymethylfurfural to 5-methylfurfural over Au/TiO2". Applied Catalysis B: Environmental. 335: 122893. doi:10.1016/j.apcatb.2023.122893.

[11] Sun, Guohan; An, Jiahuan; Hu, Hong; Li, Changzhi; Zuo, Songlin; Xia, Haian (2019). "Green catalytic synthesis of 5-methylfurfural by selective hydrogenolysis of 5-hydroxymethylfurfural over size-controlled Pd nanoparticle catalysts". Catalysis Science & Technology. 9 (5): 1238–1244. doi:10.1039/C9CY00039A. ISSN 2044-4753.

[12] Dong, Lin; Morales-Vidal, Jordi; Mu, Lili; Li, Licheng; López, Núria; Pérez-Ramírez, Javier; Chen, Zupeng (October 2023). "Selective hydrogenolysis of 5-hydroxymethylfurfural to 5-methylfurfural over Au/TiO2". Applied Catalysis B: Environmental. 335: 122893. doi:10.1016/j.apcatb.2023.122893.

[11] Feng, Yunchao; Li, Zheng; Long, Sishi; Sun, Yong; Tang, Xing; Zeng, Xianhai; Lin, Lu (2020). "Direct conversion of biomass derived l -rhamnose to 5-methylfurfural in water in high yield". Green Chemistry. 22 (18): 5984–5988. doi:10.1039/D0GC02105A. ISSN 1463-9262.

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