2,5-Bis(hydroxymethyl)tetrahydrofuran

Base Information

• Chemical Name: 2,5-Bis(hydroxymethyl)tetrahydrofuran
• CAS No.: 104-80-3
• Molecular Formula: C₆H₁₂O₃
• Molecular Weight: 132.159
• Hs Code.: 2932190090
• European Community (EC) Number: 203-239-0
• NSC Number: 40741
• DSSTox Substance ID: DTXSID40870446
• Nikkaji Number: J182.187C
• Wikidata: Q22829751
• Mol file: 104-80-3.mol

Synonyms:104-80-3;2,5-Bishydroxymethyl Tetrahydrofuran;(tetrahydrofuran-2,5-diyl)dimethanol;2,5-Dihydroxymethyl tetrahydrofuran;[5-(hydroxymethyl)oxolan-2-yl]methanol;2,5-Bis(hydroxymethyl)tetrahydrofuran;THF glycol;2,5-Tetrahydrofurandimethanol;Tetrahydro-2,5-furandimethanol;2,5-Anhydro-3,4-dideoxyhexitol;2,5-dihydroxymethyltetrahydrofuran;tetrahydrofuran-2,5-dimethanol;NSC 40741;[5-(Hydroxymethyl)tetrahydrofuran-2-yl]methanol;UNII-FHV49N1484;EINECS 203-239-0;MFCD03703415;2,5-Bis[hydroxymethyl]tetrahydrofuran;SCHEMBL697399;DTXSID40870446;2,5-Furandimethanol, tetrahydro-;Hexitol,5-anhydro-3,4-dideoxy-;FHV49N1484;2,5-bishydroxymethyltetrahydrofuran;AMY32262;NSC40741;2,5-bis-hydroxymethyltetrahydrofuran;GEO-03378;NSC-40741;STL280147;2,5-bis-hydroxymethyl tetrahydrofuran;AKOS006277000;Hexitol, 2,5-anhydro-3,4-dideoxy-;CS-T-49336;BS-42387;SY019156;CS-0217809;FT-0653706;FT-0663299;FT-0727596;(5-hydroxymethyltetrahydrofuran-2-yl)methanol;EN300-85887;D85677;A1-24378;J-507348;Q22829751

Chemical Property of 2,5-Bis(hydroxymethyl)tetrahydrofuran

Chemical Property:

• Vapor Pressure: 0.002mmHg at 25°C
• Melting Point: <-50℃
• Refractive Index: 1.4810 (589.3 nm 17.5℃)
• Boiling Point: 261.6 °C at 760 mmHg
• PKA: 14.14±0.10(Predicted)
• Flash Point: 112 °C
• PSA: 49.69000
• Density: 1.13 g/cm³
• LogP: -0.48140
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility.: Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 132.078644241
• Heavy Atom Count: 9
• Complexity: 74.4

Purity/Quality:

98% min ^*data from raw suppliers

2,5-BishydroxymethylTetrahydrofuran ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(OC1CO)CO
• Uses: Organic synthesis, humectant, solvent.

Technology Process of 2,5-Bis(hydroxymethyl)tetrahydrofuran

There total 98 articles about 2,5-Bis(hydroxymethyl)tetrahydrofuran 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: 25.4%

5-hydroxymethyl-tetrahydrofuran-2-carbaldehyde (69924-30-7) → 2,5-dimethyltetrahydrofuran (1003-38-9) + tetrahydrofuran-2,5-dimethanol (104-80-3,1122-89-0,2144-40-3,81370-88-9,81370-89-0) + 2,5-dimethylfuran (625-86-5) + 2-hydroxymethyl-5-methylfuran (3857-25-8) + 5-methyltetrahydro-2-furaldehyde (37493-29-1)

Guidance literature:

With hydrogen; In 1,4-dioxane; at 180 ℃; for 4h; under 9000.9 Torr; Reagent/catalyst; Overall yield = 100 %; Catalytic behavior;

DOI:10.1039/c5gc00062a

Reference yield: 13.0%

2,5-dimethylfuran (625-86-5) → 2,5-dimethyltetrahydrofuran (1003-38-9) + tetrahydro-5-methyl-2-furanmethanol (6126-49-4) + tetrahydrofuran-2,5-dimethanol (104-80-3,1122-89-0,2144-40-3,81370-88-9,81370-89-0)

Guidance literature:

With palladium on activated charcoal; hydrogen; In tetrahydrofuran; at 150 ℃; under 6000.6 Torr;

DOI:10.1002/cssc.201402530

Reference yield: 11.0%

5-hydroxymethyl-tetrahydrofuran-2-carbaldehyde (69924-30-7) → 2,5-dimethyltetrahydrofuran (1003-38-9) + tetrahydrofuran-2,5-dimethanol (104-80-3,1122-89-0,2144-40-3,81370-88-9,81370-89-0) + 2,5-dimethylfuran (625-86-5) + 2,5-bis-(hydroxymethyl)furan (1883-75-6) + 2-hydroxymethyl-5-methylfuran (3857-25-8) + 5-methyltetrahydro-2-furaldehyde (37493-29-1)

Guidance literature:

With hydrogen; In 1,4-dioxane; at 180 ℃; for 4h; under 9000.9 Torr; Overall yield = 100 %; Catalytic behavior;

DOI:10.1039/c5gc00062a

upstream raw materials:

1,5-Hexadien

5-hydroxymethyl-2-furfuraldehyde

2,5-bis-(hydroxymethyl)furan

5-acetoxymethyl-2-furaldehyde

Downstream raw materials:

2,5-Bis-acetoxymethyl-tetrahydro-furan

Tetrahydropyran-2-methanol

hexahydro-2H-oxepin-2-one

hexane-1,2,6-triol

Refernces

• 1、 Perret, Noémie,Grigoropoulos, Alexios,Zanella, Marco,Manning, Troy D.,Claridge, John B.,Rosseinsky, Matthew J.. "Catalytic Response and Stability of Nickel/Alumina for the Hydrogenation of 5-Hydroxymethylfurfural in Water". . p. 521 - 531. Retrieved 2016.
• 2、 Chen, Bingfeng,Han, Buxing,Li, Shaopeng,Liu, Huizhen,Shen, Xiaojun,Wang, Yanyan,Yang, Youdi. "Selective hydrogenation of aromatic furfurals into aliphatic tetrahydrofurfural derivatives". . p. 4937 - 4942. Retrieved 2020.
• 3、 Liu, Fei,Audemar, Ma?té,De Oliveira Vigier, Karine,Clacens, Jean-Marc,De Campo, Floryan,Jér?me, Fran?ois. "Palladium/carbon dioxide cooperative catalysis for the production of diketone derivatives from carbohydrates". . p. 2089 - 2093. Retrieved 2014.
• 4、 Chen, Jiazhi,Lu, Fang,Zhang, Junjie,Yu, Weiqiang,Wang, Feng,Gao, Jin,Xu, Jie. "Immobilized Ru clusters in nanosized mesoporous zirconium silica for the aqueous hydrogenation of furan derivatives at room temperature". . p. 2822 - 2826. Retrieved 2013.
• 5、 Li, Xiang,Deng, Qiang,Zhang, Likang,Wang, Jun,Wang, Rong,Zeng, Zheling,Deng, Shuguang. "Highly efficient hydrogenative ring-rearrangement of furanic aldehydes to cyclopentanone compounds catalyzed by noble metals/MIL-MOFs". . p. 152 - 158. Retrieved 2019.
• 6、 Duan, Ying,Zheng, Min,Li, Dongmi,Deng, Dongsheng,Ma, Lu-Fang,Yang, Yanliang. "Conversion of HMF to methyl cyclopentenolone using Pd/Nb2O5 and Ca-Al catalysts: Via a two-step procedure". . p. 5103 - 5113. Retrieved 2017.
• 7、 Li, Jiachen,Feng, Yunchao,Wang, Huiqiang,Tang, Xing,Sun, Yong,Zeng, Xianhai,Lin, Lu. "Highly selective ring rearrangement of 5-hydroxymethylfurfural to 3-hydroxymethylcyclopentanon catalyzed by non-noble Ni-Fe/Al2O3". . . Retrieved 2021.
• 8、 Ramos, Rubén,Grigoropoulos, Alexios,Griffiths, Ben L.,Katsoulidis, Alexandros P.,Zanella, Marco,Manning, Troy D.,Blanc, Frédéric,Claridge, John B.,Rosseinsky, Matthew J.. "Selective conversion of 5-hydroxymethylfurfural to diketone derivatives over Beta zeolite-supported Pd catalysts in water". . p. 224 - 233. Retrieved 2019.
• 9、 Qian, Yang,Li, Ze-Jun,Du, Xian-Long,Zhang, Qi,Zhao, Yi,Liu, Yong-Mei,Cao, Yong. "Total hydrogenation of bio-derived furans over supported Ru subnanoclusters prepared via amino acid-assisted deposition". . p. 850 - 859. Retrieved 2020.
• 10、 Kataoka, Hiroto,Kosuge, Daichi,Ogura, Keiji,Ohyama, Junya,Satsuma, Atsushi. "Reductive conversion of 5-hydroxymethylfurfural to 1,2,6-hexanetriol in water solvent using supported Pt catalysts". . p. 60 - 65. Retrieved 2020.