2,5-Furandimethanol

Base Information

• Chemical Name: 2,5-Furandimethanol
• CAS No.: 1883-75-6
• Molecular Formula: C6H8O3
• Molecular Weight: 128.128
• Hs Code.: 29321900
• European Community (EC) Number: 217-544-1
• NSC Number: 524614,40737
• UNII: 4XE4JYN4G7
• DSSTox Substance ID: DTXSID2062036
• Nikkaji Number: J199.705J
• Wikipedia: 2,5-Bis(hydroxymethyl)furan
• Wikidata: Q4596786
• Metabolomics Workbench ID: 60913
• ChEMBL ID: CHEMBL4303433
• Mol file: 1883-75-6.mol

Synonyms:2,5-bis(hydroxymethyl)furan;BHMF

Chemical Property of 2,5-Furandimethanol

Chemical Property:

• Appearance/Colour: Off-white to pale yellow solid
• Vapor Pressure: 0.00248mmHg at 25°C
• Melting Point: 74-77 °C
• Refractive Index: 1.542
• Boiling Point: 275.4 °C at 760 mmHg
• PKA: 13.74±0.10(Predicted)
• Flash Point: 120.3 °C
• PSA: 53.60000
• Density: 1.283 g/cm³
• LogP: 0.26420
• Storage Temp.: Refrigerator
• Solubility.: Acetonitrile (Slightly), DMSO (Slightly)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 128.047344113
• Heavy Atom Count: 9
• Complexity: 74.4

Purity/Quality:

99% ^*data from raw suppliers

5-(Hydroxymethyl)furfurylAlcohol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: C1=C(OC(=C1)CO)CO
• Description: 2,5-Furandimethanol is white or internally white solid in appearance, soluble in water, ethanol, acetone, pyridine, tetrahydrofuran, but insoluble in ethane, toluene, and dichloroethane. 5-(Hydroxymethyl)furfuryl alcohol is a heterocyclic organic compound that is naturally produced by certain wood-inhabiting fungi. It can be derived by the reduction of the formyl group of 5-hydroxymethylfurfural. 5-(Hydroxymethyl)furfuryl alcohol can be used as a building block in the enzymatic synthesis of biobased polyesters.
• Uses: 5-(Hydroxymethyl)furfuryl Alcohol is a secondary metabolite of Xylaramide, a new antifungal compound.

Technology Process of 2,5-Furandimethanol

There total 178 articles about 2,5-Furandimethanol 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: 85.0%

5-hydroxymethyl-2-furfuraldehyde (67-47-0) → 2,5-bis-(hydroxymethyl)furan (1883-75-6) + 2-hydroxymethyl-5-methylfuran (3857-25-8)

Guidance literature:

With Cu⁽⁶⁶⁾-ZnO; hydrogen; In butan-1-ol; at 100 ℃; for 4h; under 11251.1 Torr; Reagent/catalyst;

DOI:10.1039/c7gc03597g

Reference yield: 58.0%

5-hydroxymethyl-2-furfuraldehyde (67-47-0) + formic acid (64-18-6) → 2,5-dimethyltetrahydrofuran (1003-38-9) + 2,5-dimethylfuran (625-86-5) + 2,5-bis-(hydroxymethyl)furan (1883-75-6) + 5-(2-furaldehyde)methyl formate (102390-86-3) + 2-(formyloxy)methyl-5-(hydroxymethyl)furan (1253934-87-0) + 2,5-hexanedione (110-13-4)

Guidance literature:

With gold nanoparticles anchored on tetragonal-phase zirconia; In toluene; at 140 ℃; for 0.5h; under 760.051 Torr; Solvent; Inert atmosphere;

DOI:10.1016/j.chempr.2018.07.007

Reference yield: 55.0%

5-hydroxymethyl-2-furfuraldehyde (67-47-0) → 2,5-dimethylfuran (625-86-5) + 2,5-bis-(hydroxymethyl)furan (1883-75-6) + 2-hydroxymethyl-5-methylfuran (3857-25-8)

Guidance literature:

With hydrogen; In tetrahydrofuran; at 220 ℃; for 1.5h; under 11251.1 Torr; Reagent/catalyst; Time;

upstream raw materials:

5-hydroxymethyl-2-furfuraldehyde

2,5-bis(hydroxymethyl)furan diacetate

2,5-diformylfurane

5-acetoxymethyl-2-furaldehyde

Downstream raw materials:

3,6-diformylpyridazine

tetrahydrofuran-2,5-dimethanol

furan-2,5-dicarboxylic acid dimethyl ester

(1R,3R,4R)-3-(benzyl(methyl)amino)-4-hydroxymethyl-1,2,3,4-tetrahydronaphthalen-1,4-olide

Refernces

• 1、 Guo, Yuanyuan,Chen, Jinzhu. "Photo-induced reduction of biomass-derived 5-hydroxymethylfurfural using graphitic carbon nitride supported metal catalysts". . p. 101968 - 101973. Retrieved 2016.
• 2、 Kucherov,Galkin,Gordeev,Ananikov. "Efficient route for the construction of polycyclic systems from bioderived HMF". . p. 4858 - 4864. Retrieved 2017.
• 3、 Yen, Andy,Choo, Ken-Loon,Yazdi, Shabnam K.,Franke, Patrick T.,Webster, Robert,Franzoni, Ivan,Loh, Charles C. J.,Poblador-Bahamonde, Amalia I.,Lautens, Mark. "Rhodium-Catalyzed Enantioselective Isomerization of meso-Oxabenzonorbornadienes to 1,2-Naphthalene Oxides". . p. 6307 - 6311. Retrieved 2017.
• 4、 Dong, Jing,Zhu, Mingming,Zhang, Gaoshuo,Liu, Yongmei,Cao, Yong,Liu, Su,Wang, Yangdong. "Highly selective supported gold catalyst for CO-driven reduction of furfural in aqueous media". . p. 1669 - 1675. Retrieved 2016.
• 5、 Roylance, John J.,Kim, Tae Woo,Choi, Kyoung-Shin. "Efficient and Selective Electrochemical and Photoelectrochemical Reduction of 5-Hydroxymethylfurfural to 2,5-Bis(hydroxymethyl)furan using Water as the Hydrogen Source". . p. 1840 - 1847. Retrieved 2016.
• 6、 Bal, Rajaram,Kumar, Abhinav,Srivastava, Rajendra. "Modulation of Ru and Cu nanoparticle contents over CuAlPO-5 for synergistic enhancement in the selective reduction and oxidation of biomass-derived furan based alcohols and carbonyls". . p. 4133 - 4148. Retrieved 2021.
• 7、 Koopman, Frank,Wierckx, Nick,De Winde, Johannes H.,Ruijssenaars, Harald J.. "Identification and characterization of the furfural and 5-(hydroxymethyl)furfural degradation pathways of Cupriavidus basilensis HMF14". . p. 4919 - 4924. Retrieved 2010.
• 8、 Wang, Xiaofeng,Zhang, Chengcheng,Jin, Baitang,Liang, Xinhua,Wang, Qingfa,Zhao, Zhe,Li, Qingbo. "Pt-Carbon interaction-determined reaction pathway and selectivity for hydrogenation of 5-hydroxymethylfurfural over carbon supported Pt catalysts". . p. 1298 - 1310. Retrieved 2021.
• 9、 Hu, Yulin,Rao, Kasanneni Tirumala Venkateswara,Xu, Chunbao Charles,Yuan, Zhongsun,Zhang, Yongsheng. "Green synthesis of heterogeneous copper-alumina catalyst for selective hydrogenation of pure and biomass-derived 5-hydroxymethylfurfural to 2,5-bis(hydroxymethyl)furan". . . Retrieved 2021.
• 10、 Bukhtiyarova, Galina A.,Bukhtiyarova, Marina V.,Bulavchenko, Olga A.,Nuzhdin, Alexey L.. "Flow hydrogenation of 5-acetoxymethylfurfural over Cu-based catalysts". . . Retrieved 2020.