2,5-Dimethylfuran

Base Information

• Chemical Name: 2,5-Dimethylfuran
• CAS No.: 625-86-5
• Molecular Formula: C6H8O
• Molecular Weight: 96.1289
• Hs Code.: 29321900
• European Community (EC) Number: 210-914-3
• NSC Number: 6220
• UN Number: 1993
• UNII: DR5HL9OJ7Y
• DSSTox Substance ID: DTXSID7022093
• Nikkaji Number: J45.569E
• Wikipedia: 2,5-Dimethylfuran
• Wikidata: Q209267
• Metabolomics Workbench ID: 45932
• ChEMBL ID: CHEMBL1416448
• Mol file: 625-86-5.mol

Synonyms:2,5-dimethylfuran

Chemical Property of 2,5-Dimethylfuran

Chemical Property:

• Appearance/Colour: clear colorless to amber liquid
• Vapor Pressure: 57.1mmHg at 25°C
• Melting Point: -62 °C
• Refractive Index: n20/D 1.441(lit.)
• Boiling Point: 93.089 °C at 760 mmHg
• Flash Point: 29°F
• PSA: 13.14000
• Density: 0.917 g/cm³
• LogP: 1.89640
• Storage Temp.: Flammables area
• Water Solubility.: Slightly miscible with water. Miscible with ethanol and fats.
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 96.057514874
• Heavy Atom Count: 7
• Complexity: 53.2
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

2,5-Dimethylfuran ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F,Xn
• Statements: 11-22-2017/11/22
• Safety Statements: 16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Ethers, Other
• Canonical SMILES: CC1=CC=C(O1)C
• Uses: 2,5-Dimethylfuran is a major metabolite of hexane with singlet oxygen scavenging ability. It is used as biofuel, biomaker for smoking, pharmaceutical intermediate and in organic synthesis. It is also used to analyze samples for the derivatization of carbonyl-containing compounds to their oximes. It is an ideal marker for detecting cigarette smoke.

Technology Process of 2,5-Dimethylfuran

There total 209 articles about 2,5-Dimethylfuran 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: 88.5%

5-hydroxymethyl-2-furfuraldehyde (67-47-0) → 2,5-dimethyltetrahydrofuran (1003-38-9) + 2,5-dimethylfuran (625-86-5) + n-hexan-2-ol (626-93-7)

Guidance literature:

With hydrogen; In 1,4-dioxane; at 180 ℃; for 15h; under 11251.1 Torr; Temperature; Sealed tube;

DOI:10.1039/c4ra09550b

Reference yield: 84.0%

5-hydroxymethyl-2-furfuraldehyde (67-47-0) → 2,5-dimethyltetrahydrofuran (1003-38-9) + 2,5-dimethylfuran (625-86-5)

Guidance literature:

With isopropyl alcohol; In decane; at 160 ℃; for 8h; under 15001.5 Torr; Reagent/catalyst; Temperature; Solvent; Pressure; Autoclave; Inert atmosphere;

Reference yield: 40.1%

5-hydroxymethyl-2-furfuraldehyde (67-47-0) → 2,5-dimethyltetrahydrofuran (1003-38-9) + 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 1h; under 11251.1 Torr;

upstream raw materials:

5-Methylfurfural

5-hexyn-2-one

acetic anhydride

2,5-hexanedione

Downstream raw materials:

1,4-dimethyl-7-oxabicyclo<2.2.1>hept-5-ene-2,3-dicarboxylic anhydride

2,5-dimethoxy-2,5-dimethyl-2,5-dihydro-furan

2-(bromomethyl)-5-methylfuran

succinic acid

Refernces

• 1、 Hopff,Hegar. "-". . p. 2016,2020. Retrieved 1961.
• 2、 Iriondo,Mendiguren,Güemez,Requies,Cambra. "2,5-DMF production through hydrogenation of real and synthetic 5-HMF over transition metal catalysts supported on carriers with different nature". . p. 286 - 295. Retrieved 2017.
• 3、 Mani, Christian Mbaya,Braun, Max,Molinari, Valerio,Antonietti, Markus,Fechler, Nina. "A High-Throughput Composite Catalyst based on Nickel Carbon Cubes for the Hydrogenation of 5-Hydroxymethylfurfural to 2,5-Dimethylfuran". . p. 3388 - 3394. Retrieved 2017.
• 4、 Wei, Zuojun,Lou, Jiongtao,Li, Zhenbin,Liu, Yingxin. "One-pot production of 2,5-dimethylfuran from fructose over Ru/C and a Lewis-Br?nsted acid mixture in: N, N -dimethylformamide". . p. 6217 - 6225. Retrieved 2016.
• 5、 Wojtaszek-Gurdak, Anna,Zielinska, Martyna,Ziolek, Maria. "MWW layered zeolites modified with niobium species - Surface and catalytic properties". . p. 89 - 97. Retrieved 2019.
• 6、 Hu, Bin,Warczinski, Lisa,Li, Xiaoyu,Lu, Mohong,Bitzer, Johannes,Heidelmann, Markus,Eckhard, Till,Fu, Qi,Schulwitz, Jonas,Merko, Mariia,Li, Mingshi,Kleist, Wolfgang,H?ttig, Christof,Muhler, Martin,Peng, Baoxiang. "Formic Acid-Assisted Selective Hydrogenolysis of 5-Hydroxymethylfurfural to 2,5-Dimethylfuran over Bifunctional Pd Nanoparticles Supported on N-Doped Mesoporous Carbon". supporting information. p. 6807 - 6815. Retrieved 2021/02/01.
• 7、 Meng, Ge,Ji, Kaiyue,Zhang, Wei,Kang, Yiran,Wang, Yu,Zhang, Ping,Wang, Yang-Gang,Li, Jun,Cui, Tingting,Sun, Xiaohui,Tan, Tianwei,Wang, Dingsheng,Li, Yadong. "Tandem catalyzing the hydrodeoxygenation of 5-hydroxymethylfurfural over a Ni3Fe intermetallic supported Pt single-atom site catalyst". . p. 4139 - 4146. Retrieved 2021/04/02.