2,5-Dimethyltetrahydrofuran

Base Information

• Chemical Name: 2,5-Dimethyltetrahydrofuran
• CAS No.: 1003-38-9
• Molecular Formula: C6H12O
• Molecular Weight: 100.161
• Hs Code.: 2932190090
• European Community (EC) Number: 213-707-6
• NSC Number: 12594
• DSSTox Substance ID: DTXSID10862510
• Nikkaji Number: J133.069A
• Mol file: 1003-38-9.mol

Synonyms:2,5-dimethyltetrahydrofuran;2,5-ME2-THF

Chemical Property of 2,5-Dimethyltetrahydrofuran

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 62.1mmHg at 25°C
• Melting Point: -45℃
• Refractive Index: n20/D 1.404(lit.)
• Boiling Point: 91 °C at 760 mmHg
• Flash Point: 26.7 °C
• PSA: 9.23000
• Density: 0.836 g/cm³
• LogP: 1.57380
• Storage Temp.: Refrigerator
• Water Solubility.: Practically insoluble in water
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 100.088815002
• Heavy Atom Count: 7
• Complexity: 53.2

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,5-Dimethyltetrahydrofuran ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:Flammable.; R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: Xi:Irritant
• Statements: 10
• Safety Statements: 16-29-33

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Ethers (
• Canonical SMILES: CC1CCC(O1)C
• Uses: 2,5-Dimethyltetrahydrofuran is used in preparation method for Hydrodeoxygenation of Oxygenated compounds to unsaturaded products.

Technology Process of 2,5-Dimethyltetrahydrofuran

There total 162 articles about 2,5-Dimethyltetrahydrofuran 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: 100.0%

hexane-2,5-diol (2935-44-6) → 2,5-dimethyltetrahydrofuran (1003-38-9)

Guidance literature:

Trichlorbutylstannan; at 81 - 83 ℃; for 4.3h;

DOI:10.1016/0040-4020(89)80027-4

Reference yield: 71.0%

hypochlorous acid 1-methyl-pentyl ester (40137-10-8) → 2,5-dimethyltetrahydrofuran (1003-38-9) + n-hexan-2-ol (626-93-7) + n-hexan-2-one (591-78-6) + 5-chlorohexan-2-ol (52355-86-9)

Guidance literature:

With sodium hydrogencarbonate; iron(II) sulfate; In tetrachloromethane; Ambient temperature; protected from the light;

DOI:10.1016/0040-4020(81)85021-1

Reference yield: 65.0%

2-methyl-5-iodomethyltetrahydrofuran (19056-49-6) → 2,5-dimethyltetrahydrofuran (1003-38-9)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1007/BF00507083

upstream raw materials:

hexane-2,5-diol

1,5-Hexadien

1,2-epoxy-5-hexene

2-methyl-5-iodomethyltetrahydrofuran

Downstream raw materials:

N-Phenyl-2,5-dimethylpyrrolidine

2,5-hexanedione

1-Iodohexane

formaldehyd

Refernces

• 1、 Liu, Yifei,Mellmer, Max A.,Alonso, David Martin,Dumesic, James A.. "Effects of Water on the Copper-Catalyzed Conversion of Hydroxymethylfurfural in Tetrahydrofuran". . p. 3983 - 3986. Retrieved 2015.
• 2、 Mitra, Joyee,Zhou, Xiaoyuan,Rauchfuss, Thomas. "Pd/C-catalyzed reactions of HMF: Decarbonylation, hydrogenation, and hydrogenolysis". . p. 307 - 313. Retrieved 2015.
• 3、 Hua, Manli,Song, Jinliang,Huang, Xin,Hou, Minqiang,Fan, Honglei,Zhang, Zhaofu,Wu, Tianbin,Han, Buxing. "Support Effect of Ru Catalysts for Efficient Conversion of Biomass-Derived 2,5-Hexanedione to Different Products". . p. 7685 - 7693. Retrieved 2021.
• 4、 Tagliavini, Giuseppe,Marton, Daniele,Furlani, Donatella. "ORGANOTINS AS ETHERIFICATION CATALYSTS. II. CATALYTIC CONVERSION OF ALCOHOLS TO OPEN-CHAIN AND CYCLIC ETHERS BY ORGANOTIN TRICHLORIDES". . p. 1187 - 1196. Retrieved 1989.
• 5、 Saha, Basudeb,Bohn, Christine M.,Abu-Omar, Mahdi M.. "Zinc-assisted hydrodeoxygenation of biomass-derived 5-hydroxymethylfurfural to 2,5-Dimethylfuran". . p. 3095 - 3101. Retrieved 2014.
• 6、 Liu, Sibao,Zheng, Weiqing,Fu, Jiayi,Alexopoulos, Konstantinos,Saha, Basudeb,Vlachos, Dionisios G.. "Molybdenum Oxide-Modified Iridium Catalysts for Selective Production of Renewable Oils for Jet and Diesel Fuels and Lubricants". . p. 7679 - 7689. Retrieved 2019.
• 7、 Liu, Sibao,Okuyama, Yasuyo,Tamura, Masazumi,Nakagawa, Yoshinao,Imai, Akio,Tomishige, Keiichi. "Catalytic conversion of sorbitol to gasoline-ranged products without external hydrogen over Pt-modified Ir-ReOx/SiO2". . p. 122 - 131. Retrieved 2016.
• 8、 Olah,Szilagyi. "-". . p. 1121,1124. Retrieved 1971.
• 9、 McLaughlin et al.. "-". . p. 112,113. Retrieved 1961.
• 10、 Chatterjee, Maya,Ishizaka, Takayuki,Kawanami, Hajime. "Hydrogenation of 5-hydroxymethylfurfural in supercritical carbon dioxide-water: A tunable approach to dimethylfuran selectivity". . p. 1543 - 1551. Retrieved 2014.