2,2,5,5-Tetramethyltetrahydrofuran

Base Information

• Chemical Name: 2,2,5,5-Tetramethyltetrahydrofuran
• CAS No.: 15045-43-9
• Molecular Formula: C8H16O
• Molecular Weight: 128.214
• Hs Code.: 2932190090
• European Community (EC) Number: 239-117-9
• UNII: 83Z08D4U0T
• DSSTox Substance ID: DTXSID1022263
• Nikkaji Number: J37.037A
• Wikipedia: 2,2,5,5-Tetramethyltetrahydrofuran
• Wikidata: Q25323734
• Metabolomics Workbench ID: 109457
• Mol file: 15045-43-9.mol

Synonyms:2,2,5,5-TETRAMETHYLTETRAHYDROFURAN;15045-43-9;Furan, tetrahydro-2,2,5,5-tetramethyl-;2,2,5,5-tetramethyloxolane;Tetrahydro-2,2,5,5-tetramethylfuran;EINECS 239-117-9;UNII-83Z08D4U0T;AI3-25141;83Z08D4U0T;Furan,tetrahydro-2,2,5,5-tetramethyl-;SCHEMBL380315;DTXSID1022263;GEO-03959;MFCD00005368;2,2,5,5-Tetramethyl tetrahydrofuran;AKOS015912795;2,2,5,5-Tetramethyl-tetrahydro-furan;AS-63484;LS-184965;FT-0609118;D92900;EN300-7353614;Q25323734

Chemical Property of 2,2,5,5-Tetramethyltetrahydrofuran

Chemical Property:

• Appearance/Colour: clear colourless liquid
• Vapor Pressure: 26.1mmHg at 25°C
• Melting Point: -92oC
• Refractive Index: n20/D 1.405(lit.)
• Boiling Point: 112 °C at 760 mmHg
• Flash Point: 3.9 °C
• PSA: 9.23000
• Density: 0.811 g/mL at 25 °C(lit.)
• LogP: 2.35400
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 128.120115130
• Heavy Atom Count: 9
• Complexity: 99.7

Purity/Quality:

99% ^*data from raw suppliers

2,2,5,5-Tetramethyltetrahydrofuran >96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11
• Safety Statements: 16-29-33

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Solvents -> Ethers (
• Canonical SMILES: CC1(CCC(O1)(C)C)C

Technology Process of 2,2,5,5-Tetramethyltetrahydrofuran

There total 22 articles about 2,2,5,5-Tetramethyltetrahydrofuran 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%

2,5-dimethyl-2,5-hexanediol (110-03-2) → 2,2,5,5-tetramethyltetrahydrofuran (15045-43-9)

Guidance literature:

With beta-zeolite HCZB 25; at 0.85 - 105 ℃; for 1.5h; Reagent/catalyst;

Reference yield: 63.0%

3-Phenyl-1-propanol (122-97-4) + 2-diethylamino-4,4,7,7-tetramethyl-1,3,2-dioxaphosphepane (261920-18-7) → 2,2,5,5-tetramethyltetrahydrofuran (15045-43-9) + bis(3-phenylpropyl) hydrophosphonate + 4,4,7,7-tetramethyl-2-oxo-2-(3-phenylpropyloxy)-1,3,2-dioxaphosphepane

Guidance literature:

3-Phenyl-1-propanol; 2-diethylamino-4,4,7,7-tetramethyl-1,3,2-dioxaphosphepane; With 1H-tetrazole; In dichloromethane; at 20 ℃; for 22h;

With 3-chloro-benzenecarboperoxoic acid; at -78 - 20 ℃; for 0.5h;

DOI:10.3987/COM-99-S89

Reference yield: 21.0%

2,5-dimethyl-2,5-hexanediol (110-03-2) → 2,2,5,5-tetramethyltetrahydrofuran (15045-43-9) + 2,5-dimethyl-4-hexen-2-ol (14908-27-1)

Guidance literature:

With chloro-trimethyl-silane; dimethyl sulfoxide; In benzene; at 20 ℃; for 75h;

DOI:10.1055/s-1983-30287

upstream raw materials:

formaldehyd

2,5-dimethyl-2,5-hexanediol

aniline hydrobromide

2,5-dimethyl-1,5-hexadiene

Downstream raw materials:

5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol

2,5-dichloro-2,5-dimethyl hexane

para-xylene

5-Benzyl-4-isopropylidene-2,2-dimethyl-3,4-dihydro-2H-pyrrole

Refernces

• 1、 Haubenstock,Hong. "Solvation effects on stereochemistry of reduction of 3,3,5-trimethylcyclohexanone with lithium aluminum tri-t-butoxyhydride". . p. 2445 - 2447. Retrieved 1978.
• 2、 Byrne, Fergal,Forier, Bart,Bossaert, Greet,Hoebers, Charly,Farmer, Thomas J.,Clark, James H.,Hunt, Andrew J.. "2,2,5,5-Tetramethyltetrahydrofuran (TMTHF): A non-polar, non-peroxide forming ether replacement for hazardous hydrocarbon solvents". supporting information. p. 3671 - 3678. Retrieved 2017/08/15.