2,3-Dihydrofuran

Base Information

• Chemical Name: 2,3-Dihydrofuran
• CAS No.: 1191-99-7
• Deprecated CAS: 27535-65-5
• Molecular Formula: C4H6O
• Molecular Weight: 70.091
• Hs Code.: 2932.90
• European Community (EC) Number: 214-747-7
• NSC Number: 85221
• UNII: 07M2EY3BG1
• DSSTox Substance ID: DTXSID9061594
• Nikkaji Number: J41.161B
• Wikipedia: 2,3-Dihydrofuran
• Wikidata: Q2813778
• Metabolomics Workbench ID: 57830
• Mol file: 1191-99-7.mol

Synonyms:2,3-dihydrofuran

Chemical Property of 2,3-Dihydrofuran

Chemical Property:

• Appearance/Colour: clear colourless liquid
• Vapor Pressure: 14.46 psi ( 55 °C)
• Melting Point: 280 °C(Solv: trichloroethylene (79-01-6); ethanol (64-17-5))
• Refractive Index: 1.415 - 1.435
• Boiling Point: 54.5 °C at 760 mmHg
• Flash Point: -24 °C
• PSA: 9.23000
• Density: 0.959 g/cm³
• LogP: 0.92040
• Storage Temp.: 2-8°C
• Water Solubility.: slightlu soluble
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 70.041864811
• Heavy Atom Count: 5
• Complexity: 47.6

Purity/Quality:

99% ^*data from raw suppliers

2,3-Dihydrofuran ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi,Xn
• Hazard Codes: F,Xi,Xn
• Statements: 11-19-36-22-2017/11/19
• Safety Statements: 16-33-39-26-18-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Ethers, Other
• Canonical SMILES: C1COC=C1
• Uses: 2,3-Dihydrofuran is a dehydration product of tetrahydrofuran (THF). 2,3-Dihydrofuran is also used in the preparation of niologically active compounds such as antitumor agents. 2,3-Dihydrofuran is a versatile reagent used in lanthanide-catalyzed Diels-Alder reactions with 2-pyrones and in Rh(II)-stabilized cycloadditions with vinylcarbenoids. It is applied for alkylation by active methylene compounds, catalyzed by trans-Dichlorobis(triphenyl-phosphine)-palladium(II). It is also used in the preparation of biologically active compounds such as antitumor agents.

Technology Process of 2,3-Dihydrofuran

There total 76 articles about 2,3-Dihydrofuran 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:

2-methoxytetrahydrofuran (13436-45-8) + ethylmagnesium bromide (925-90-6) → 2-ethoxytetrahydrofuran (13436-46-9) + 2,3-dihydro-2H-furan (1191-99-7,75454-45-4)

Guidance literature:

In benzene; for 3h; Heating;

DOI:10.1007/BF00475242

Reference yield:

2-methoxytetrahydrofuran (13436-45-8) → 2-ethoxytetrahydrofuran (13436-46-9) + 2,3-dihydro-2H-furan (1191-99-7,75454-45-4)

Guidance literature:

With ethylmagnesium bromide; In benzene; for 3h; Heating;

DOI:10.1007/BF00475242

Reference yield:

2,5-dihydrofuran (1708-29-8) + carbon monoxide (201230-82-2) → 2,3-dihydro-2H-furan (1191-99-7,75454-45-4) + tetrahydrofuran-2-carbaldehyde (7681-84-7) + (R)-tetrahydrofuran-3-carboxaldehyde (191347-92-9) + (S)-tetrahydrofuran-3-carboxaldehyde

Guidance literature:

With acetylacetonatodicarbonylrhodium(l); hydrogen; (R,S)-binaphos; In benzene; at 40 ℃; for 6h; under 760 Torr; Mechanism; Product distribution; other heterocyclic olefins, other reagent: (R)-2-(diphenylphosphino)-1,1'-binaphthalen-2'-yl (S)-1,1'-binaphthalene-2,2'-diyl phosphite, other pressure, other temperature, other reaction time;

DOI:10.1021/jo9624051

upstream raw materials:

Tetrahydrofurfuryl alcohol

2,5-dihydrofuran

potassium tert-butylate

tert-butyl alcohol

Downstream raw materials:

ethyl 2-oxabicyclo[3.1.0]hexane-6-carboxylate

2-chlorotetrahydrofuran

4,5-dihydro-3-carboxylic acid chloride

2-ethoxytetrahydrofuran

Refernces

• 1、 Luckay, Robert C.,Sheng, Xia,Strasser, Christoph E.,Raubenheimer, Helgard G.,Safin, Damir A.,Babashkina, Maria G.,Klein, Axel. "Aerial oxidation of tetrahydrofuran to 2-hydroxotetrahydrofuran in the presence of a trimeric CuI complex [Cu3L3] (HL = tBuNHC(S)NHP(S)(OiPr)2) and trapping of the unstable product at recrystallization". . p. 2835 - 2840. Retrieved 2010.
• 2、 Matsuhashi, Hiromi,Hattori, Hideshi,Tanabe, Kozo. "DOUBLE BOND MIGRATION OF ALLYL ETHERS OVER SOLID BASE CATALYSTS". . p. 341 - 342. Retrieved 1981.
• 3、 Mazuela, Javier,Pmies, Oscar,Dieguez, Montserrat,Palais, Laetitia,Rosset, Stephane,Alexakis, Alexandre. "Fine-tunable monodentate phosphoroamidite and aminophosphine ligands for Rh-catalyzed asymmetric hydroformylation". . p. 2153 - 2157. Retrieved 2010.
• 4、 Ye, Baihua,Zhao, Jie,Zhao, Ke,McKenna, Jeffrey M.,Toste, F. Dean. "Chiral Diaryliodonium Phosphate Enables Light Driven Diastereoselective α-C(sp3)-H Acetalization". . p. 8350 - 8356. Retrieved 2018.
• 5、 Polivin, Yu. N.,Trofimova, M. V.,Karakhanov, R. A.,Ageev, E. A.. "Synthesis and Properties of Furan Derivatives 2. Role of the Halogen in RMgX in Reactions with Alkoxytetrahydrofurans". . p. 494 - 496. Retrieved 1992.
• 6、 Dieguez, Montserrat,Pamies, Oscar,Claver, Carmen. "First successful application of diphosphite ligands in the asymmetric hydroformylation of dihydrofurans". . p. 1221 - 1223. Retrieved 2005.
• 7、 -. "Olefin reaction in the catalyst and the olefin production". Paragraph 0109-0111; 0129-0132; 0134-0135; 0150. . Retrieved 2020/10/31.