cis-2,5-Dimethyltetrahydrofuran

Base Information

• Chemical Name: cis-2,5-Dimethyltetrahydrofuran
• CAS No.: 2144-41-4
• Molecular Formula: C6H12 O
• Molecular Weight: 100.161
• UNII: O7NB7572GU
• Nikkaji Number: J100.738F
• Wikidata: Q27285445
• Mol file: 2144-41-4.mol

Synonyms:2144-41-4;cis-2,5-Dimethyltetrahydrofuran;cis-2,5-Dimethyloxolane;2,5-Dimethyloxolane, cis-;(2R,5S)-2,5-dimethyloxolane;Furan, tetrahydro-2,5-dimethyl-, cis-;O7NB7572GU;cis-Tetrahydro-2,5-Dimethylfuran;Rel-(2R,5S)-2,5-dimethyltetrahydrofuran;starbld0003326;UNII-O7NB7572GU;SCHEMBL9062787;OXMIDRBAFOEOQT-OLQVQODUSA-N;2,5-Dimethyltetrahydrofuran, (Z)-;Tetrahydro-2beta,5beta-dimethylfuran;Q27285445;FURAN, TETRAHYDRO-2,5-DIMETHYL-, (2R,5S)-REL-

Chemical Property of cis-2,5-Dimethyltetrahydrofuran

Chemical Property:

• Boiling Point: 91°Cat760mmHg
• Flash Point: 26.7°C
• PSA: 9.23000
• Density: 0.836g/cm³
• LogP: 1.57380
• 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:

cis-2,5-Dimethyltetrahydrofuran ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(O1)C
• Isomeric SMILES: C[C@@H]1CC[C@@H](O1)C
• Uses: cis-2,5-Dimethyltetrahydrofuran is a byproduct of the catalytic conversion of sugars and polyols to biomass-derived carbohydrates. Dihydrofuranyl derivative.

Technology Process of cis-2,5-Dimethyltetrahydrofuran

There total 14 articles about cis-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: 58.0%

5-hydroxymethyl-2-furfuraldehyde (67-47-0) → 2,5-dimethylfuran (625-86-5) + (2R,5S)-2,5-dimethyltetrahydrofuran (2144-41-4) + (+/-)-trans-2,5-dimethyltetrahydrofuran (38484-59-2)

Guidance literature:

With hydrogen; In isopropyl alcohol; at 220 ℃; for 4h; under 7500.75 Torr; Pressure; Reagent/catalyst; Temperature; Time; Overall yield = 64 %; Kinetics; Green chemistry;

DOI:10.1039/c4cy01376j

Reference yield: 32.0%

5-hydroxymethyl-2-furfuraldehyde (67-47-0) → 2,5-dimethylfuran (625-86-5) + n-hexan-2-ol (626-93-7) + (2R,5S)-2,5-dimethyltetrahydrofuran (2144-41-4) + (+/-)-trans-2,5-dimethyltetrahydrofuran (38484-59-2)

Guidance literature:

With methanol; at 320 ℃; for 0.75h; Temperature; Time; Supercritical conditions;

DOI:10.1039/c2gc35667h

Reference yield:

1,2-epoxy-5-hexene (10353-53-4) → oxepane (592-90-5) + 2-methyloxane (10141-72-7) + (2R,5S)-2,5-dimethyltetrahydrofuran (2144-41-4) + (+/-)-trans-2,5-dimethyltetrahydrofuran (38484-59-2)

Guidance literature:

With bromine; tri-n-butyl-tin hydride; Multistep reaction; 1.) CCl₄, 20 deg C;

DOI:10.1016/S0040-4039(00)99071-3

upstream raw materials:

1,2-epoxy-5-hexene

(+/-)-trans-2,5-dimethyltetrahydrofuran

(2R,5R)-2,5-hexanediol

5-hydroxymethyl-2-furfuraldehyde

Downstream raw materials:

2,5-dimethyl-2,3-dihydrofuran

n-hexan-2-ol

n-hexan-2-one

methylcyclopropane

Refernces

• 1、 Nagpure, Atul S.,Venugopal, Ashok Kumar,Lucas, Nishita,Manikandan, Marimuthu,Thirumalaiswamy, Raja,Chilukuri, Satyanarayana. "Renewable fuels from biomass-derived compounds: Ru-containing hydrotalcites as catalysts for conversion of HMF to 2,5-dimethylfuran". . p. 1463 - 1472. Retrieved 2015.
• 2、 Scholz, David,Aellig, Christof,Hermans, Ive. "Catalytic transfer hydrogenation/hydrogenolysis for reductive upgrading of furfural and 5-(hydroxymethyl)furfural". . p. 268 - 275. Retrieved 2014/03/21.