5-Hydroxymethylfurfural

Base Information

• Chemical Name: 5-Hydroxymethylfurfural
• CAS No.: 67-47-0
• Deprecated CAS: 76330-16-0
• Molecular Formula: C6H6O3
• Molecular Weight: 126.112
• Hs Code.: 29321900
• European Community (EC) Number: 200-654-9
• NSC Number: 40738
• UNII: 70ETD81LF0
• DSSTox Substance ID: DTXSID3030428
• Nikkaji Number: J4.850J
• Wikipedia: Hydroxymethylfurfural
• Wikidata: Q414606
• Metabolomics Workbench ID: 46497
• ChEMBL ID: CHEMBL185885
• Mol file: 67-47-0.mol

Synonyms:5-(hydroxymethyl)furfural;5-HM-2-F cpd;5-HMF cpd;5-hydroxymethyl furfural;5-hydroxymethyl-2-furaldehyde;5-hydroxymethyl-2-furfural;5-hydroxymethylfuraldehyde;5-hydroxymethylfurfural;5-hydroxymethylfurfuraldehyde;Aes-103;hydroxymethylfurfural

Chemical Property of 5-Hydroxymethylfurfural

Chemical Property:

• Appearance/Colour: Beige coloured crystalline solid
• Vapor Pressure: 0.000891mmHg at 25°C
• Melting Point: 30-34 °C
• Refractive Index: n20/D 1.562(lit.)
• Boiling Point: 291.5 °C at 760 mmHg
• PKA: 12.82±0.10(Predicted)
• Flash Point: 79.4 °C
• PSA: 50.44000
• Density: 1.29 g/cm³
• LogP: 0.58440
• Storage Temp.: 2-8°C
• Sensitive.: Air & Light Sensitive
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in water, alcohol, ethyl acetate, acetone, dimethylformamide, benzene, ether and chloroform.
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 126.031694049
• Heavy Atom Count: 9
• Complexity: 103

Purity/Quality:

98% ^*data from raw suppliers

5-Hydroxymethylfurfural ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-52/53
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aldehydes
• Canonical SMILES: C1=C(OC(=C1)C=O)CO
• Recent ClinicalTrials: Evaluation of Different Dose Regimens of Aes-103 Given for 28 Days to Subjects With Stable Sickle Cell Disease
• Recent EU Clinical Trials: A Phase 2, Exploratory, Placebo-Controlled, Multicenter, Double-Blind Evaluation of the Safety, Pharmacokinetics, Pharmacodynamics, and Clinical Effects of Five Dose Regimens of Aes-103 Given for 28 Days to Subjects with Stable Sickle Cell Disease
• Description: 5-Hydroxymethylfurfural (5-HMF) derived from sugars is the link between biomass and furan-based chemicals. With its various functional groups and associated reaction sites, this small molecule opens the door to a wide range of chemical modifications, which makes 5-HMF a versatile renewable building block.5-HMF is widely spread in food products and is formed in sugar containing food when exposed to heat. It is widely used as an indicator of quality in food products. It is also employed to indicate the adulteration of food products with acid converted invert syrups.
• Uses: An antioxidant for grape and apple juice. As an indicator for excess heat-treatment in sugar-containing food. 5-Hydroxymethyl-2-furaldehyde is used as an intermediate of OMBF (5,5'-oxydimethylenebis(2- furfural)), crown ethers. It is used in organic synthesis to prepare dialdehydes, glycols, ethers, amino alcohols and acetals. It acts as an antioxidant found in some fruit juices and caramel products. 5-Hydroxymethylfurfural is a chemical substance produced by dehydration of glucose or fructose. The molecule contains a furan ring, an aldehyde group and a hydroxymethyl group. The chemical properties are relatively lively. 5-Hydroxymethylfurfural can prepare various derivatives through oxidation, hydrogenation and condensation, and is an important fine chemical raw material. 5-Hydroxymethylfurfural is a furfural compound with a furan ring structure produced by dehydration of monosaccharide compounds such as glucose under high temperature or weak acid conditions. It is an endogenous pollutant with potential safety hazards. 5-Hydroxymethylfurfural is an important chemical raw material. Its molecule contains an aldehyde group and a hydroxymethyl group, which can be used to synthesize many useful compounds and new polymer materials through hydrogenation, oxidative dehydrogenation, esterification, halogenation, polymerization, hydrolysis and other chemical reactions, including Medicine, resin-based plastics, diesel fuel additives, etc.

Technology Process of 5-Hydroxymethylfurfural

There total 708 articles about 5-Hydroxymethylfurfural which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

α-D-fructofuranose (10489-79-9) → 5-methyl-2-furanone (591-12-8) + 5-hydroxy-5-methyl-dihydro-furan-2-one (53179-31-0) + 5-hydroxymethyl-2-furfuraldehyde (67-47-0) + β-D-glucose (492-61-5)

Guidance literature:

platinum(II) chloride; In 1-ethyl-3-methyl-1H-imidazol-3-ium chloride; at 80 ℃; for 3h; Product distribution / selectivity;

Reference yield: 56.4%

methanol (67-56-1) + α-D-fructofuranose (10489-79-9) → 5-hydroxymethyl-2-furfuraldehyde (67-47-0) + 5-(methoxymethyl)-2-furaldehyde (1917-64-2) + levulinic acid methyl ester (624-45-3) + 2-(dimethoxymethyl)-5-(methoxymethyl)furan (110339-34-9)

Guidance literature:

With C₇H₇NO₂*3H⁽¹⁺⁾*O₄₀PW₁₂^(3-); at 120 ℃; for 10h; Reagent/catalyst; Catalytic behavior; Sealed tube;

DOI:10.1039/c8ra02278j

Reference yield: 24.0%

methanol (67-56-1) + D-Fructose (57-48-7,18875-34-8) → 5-hydroxymethyl-2-furfuraldehyde (67-47-0) + 5-(methoxymethyl)-2-furaldehyde (1917-64-2)

Guidance literature:

In hexane; at 100 ℃; for 0.0833333h; Ionic liquid; Sealed tube; Green chemistry;

DOI:10.1039/c2gc35175g

upstream raw materials:

5-chloromethylfurfural

5-bromomethyl-furan-2-carbaldehyde

ethanol

silver(I) acetate

Refernces

• 1、 Sugimura, Hideyuki,Kikuchi, Mao,Kato, Saori,Sekita, Wataru,Sasaki, Ikuo. "Practical synthesis of mumefural, a component of Japanese apricot juice concentrate". . p. 7638 - 7641. Retrieved 2016.
• 2、 Shi, Xian-Lei,Lin, Huikun,Tao, Minli,Zhang, Wenqin,Zhang, Min,Li, Yongdan. "Bifunctional polyacrylonitrile fiber-mediated conversion of sucrose to 5-hydroxymethylfurfural in mixed-aqueous systems". . p. 572 - 578. Retrieved 2015.
• 3、 Wang, Xin,Lv, Tao,Wu, Minghui,Sui, Junwei,Liu, Qing,Liu, Huan,Huang, Jiaojiao,Jia, Lishan. "Aluminum doped solid acid with suitable ratio of Br?nsted and Lewis acid sites synthesized by electric-flocculation of phosphotungstic acid via hydrothermal treatment for producing 5-hydroxymethylfurfural from glucose". . p. 87 - 96. Retrieved 2019.
• 4、 Shi, Jincai,Gao, Haiyan,Xia, Yongmei,Li, Wei,Wang, Haijun,Zheng, Changge. "Efficient process for the direct transformation of cellulose and carbohydrates to 5-(hydroxymenthyl)furfural with dual-core sulfonic acid ionic liquids and co-catalysts". . p. 7782 - 7790. Retrieved 2013.
• 5、 Dutta, Arghya,Gupta, Dinesh,Patra, Astam K.,Saha, Basudeb,Bhaumik, Asim. "Synthesis of 5-hydroxymethylfurural from carbohydrates using large-pore mesoporous tin phosphate". . p. 925 - 933. Retrieved 2014.
• 6、 Gao, Heping,Pan, Jianming,Han, Donglai,Zhang, Yunlei,Shi, Weidong,Zeng, Jun,Peng, Yinxian,Yan, Yongsheng. "Facile synthesis of microcellular foam catalysts with adjustable hierarchical porous structure, acid-base strength and wettability for biomass energy conversion". . p. 13507 - 13518. Retrieved 2015.
• 7、 Huang, Zhen,Pan, Yuanjia,Guo, Jia,Chao, Yimin,Shen, Wei,Wang, Changchun,Xu, Hualong. "Electron-withdrawing ability tunable polyphosphazene frameworks as novel heterogeneous catalysts for efficient biomass upgrading". . p. 48694 - 48698. Retrieved 2016.
• 8、 Ma, Hao,Li, Zhenzhen,Chen, Lili,Teng, Junjiang. "LiCl-promoted-dehydration of fructose-based carbohydrates into 5-hydroxymethylfurfural in isopropanol". . p. 1404 - 1410. Retrieved 2021.
• 9、 Dibenedetto, Angela,Aresta, Michele,Di Bitonto, Luigi,Pastore, Carlo. "Organic Carbonates: Efficient Extraction Solvents for the Synthesis of HMF in Aqueous Media with Cerium Phosphates as Catalysts". . p. 118 - 125. Retrieved 2016.
• 10、 Dinh Dang, Minh Huy,Le Hoang Doan, Tan,Phan, Ha Bich,Thuy Nguyen, Linh Ho,Tran, Phuong Hoang,Vo, Huong Thi. "Synthesis of 5-hydroxymethylfurfural from monosaccharides catalyzed by superacid VNU-11-SO4in 1-ethyl-3-methylimidazolium chloride ionic liquid". . p. 39687 - 39692. Retrieved 2020.