5905-00-0

Basic information

• Product Name: 2,2'-Bifuran
• Synonyms: 2,2'-Bifuran;2,2'-Bifuryl;2,2'-Difuryl
• CAS NO: 5905-00-0
• Molecular Formula: C₈H₆O₂
• Molecular Weight: 134.13
• Mol File: 5905-00-0.mol

Chemical Properties

• Melting Point: 5 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 240-245 °C(Press: 7 Torr)
• Appearance: /
• Density: 1.114±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2,2'-Bifuran(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Bifuran(5905-00-0)
• EPA Substance Registry System: 2,2'-Bifuran(5905-00-0)

Safety Data

• Hazardous Substances Data: 5905-00-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,2'-Bifuran is used as a building block in organic synthesis for its ability to form a variety of complex organic compounds. Its unique structure allows for the creation of new molecules with potential applications in various industries.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 2,2'-Bifuran is used as a key intermediate in the production of various pharmaceuticals. Its role in the synthesis of active pharmaceutical ingredients (APIs) is crucial for developing new drugs with specific therapeutic properties.
Used in Agrochemical Development:
2,2'-Bifuran is also utilized in the agrochemical sector as an intermediate for the synthesis of pesticides and other agrochemicals. Its contribution to the development of effective and safe products for agricultural use is significant.
Used in Fine Chemicals:
In the fine chemicals industry, 2,2'-Bifuran is employed for the synthesis of specialty chemicals that have specific applications in areas such as fragrances, dyes, and other high-value products.
Used in Advanced Materials Development:
2,2'-Bifuran is used in the development of advanced materials due to its potential to enhance the properties of various materials, such as improving their thermal stability, mechanical strength, or electrical conductivity.
Used as a Ligand in Coordination Chemistry:
In coordination chemistry, 2,2'-Bifuran serves as a ligand, which allows it to bind to metal ions to form coordination compounds. These compounds have applications in catalysis, sensing, and other areas of chemistry.
Used in Organic Electronic Devices:
2,2'-Bifuran has been studied for its potential applications in organic electronic devices, such as organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs), due to its electronic properties and ability to form stable complexes with other molecules.
Used in Functionalized Polymers:
As a building block for functionalized polymers, 2,2'-Bifuran contributes to the development of polymers with specific properties, such as improved thermal stability, mechanical strength, or chemical resistance, which are useful in various industrial applications.

Upstream product

• 5905-06-6 [2,2']bifuranyl-3-carboxylic acid 
• 110-00-9 furan 
• 584-12-3 2-bromofuran 
• 54829-48-0 2-iodofuran 
• 527-69-5 2-furancarbonyl chloride 
• 51583-40-5 2-(trimethylstannyl)furan 
• 98-88-4 benzoyl chloride 
• 39838-95-4 2-furylcopper 
• 80421-32-5 5-Iodo-2,2'-bifuran 
• 114085-60-8 Acetic acid 4-furan-2-yl-2-hydroxy-4-oxo-butyl ester 
• 81745-86-0 2-furylzinc chloride 
• 590-17-0 cyanomethyl bromide 
• 17763-80-3 para-nitrophenyl triflate 
• 586-78-7 para-nitrophenyl bromide 

Downstream Products

• 1592-33-2 octahydro-2,2′-bifuran 
• 16303-60-9 [2,2']bifuranyl-5-carbaldehyde 
• 62889-09-2 2,2':5',2''-trifuran 
• 80421-31-4 2,2':5',2'':5'',2'''-quaterfuran 
• 38299-97-7 2-(tetrahydrofuran-2-yl)furan 
• 132381-00-1 5,5'-Bis(dicyanomethylene)-5,5'-dihydro-Δ^2,2'-bifuran 
• 132381-01-2 3,3'-Dibromo-5,5'-bis(dicyanomethylene)-5,5'-dihydro-Δ^2,2'-bifuran 
• 1192739-17-5 [2,2'-bifuran]-5-yltributylstannane 
• 1620697-29-1 3''',4''-di-n-heptyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexifuran 
• 1620697-27-9 2-([2,2′-bifuran]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1445682-79-0 5,5’-bis(2-thienyl)-2,2’-bifuran 
• 1258844-12-0 5,5’-bis(4-methylphenyl)-2,2’-bifuran 

Relevant articles and documents

METHOD FOR PRODUCING HETEROLE MULTIMER

PROBLEM TO BE SOLVED: To provide a method for producing a heterole multimer at low cost and in high yields. SOLUTION: A method for producing a heterole multimer has a deprotonation step in which, in the presence of a deprotonation agent and a deprotonation promoter for heteroles, heteroles are deportonated, and a coupling step in which the deprotonated heteroles form a carbon-carbon bond. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Palladium-catalyzed homo-coupling of heteroarylsulfoniums via borylation/Suzuki-Miyaura coupling sequence

Palladium-catalyzed homo-coupling of heteroaryldimethylsulfoniums proceeds in the presence of bis(pinacolato)diboron and a base to yield biheteroaryls. The homo-coupling involves palladium-catalyzed borylation and the subsequent Suzuki-Miyaura coupling. As the sulfoniums were able to be prepared in situ from the corresponding heteroaryl sulfides and methyl triflate, one-pot transformations of heteroaryl sulfides into the homo-coupling products were executed. Furthermore, a facile synthesis of a highly substituted 2,2'-bibenzofuran was accomplished with a combination of Pummerer-type synthesis of 2-benzofuryl sulfide and the present homo-coupling.

Synthesis of 2,5-Disubstituted Furans from Sc(OTf)3 Catalyzed Reaction of Aryl Oxiranediesters with γ-Hydroxyenones

A convenient synthesis of 2,5-disubstituted furan was developed by employing donor-acceptor oxiranes in a new reaction with γ-hydroxyenones. Sc(OTf)3 was found to be the best catalyst, and 2,5-disubstituted furans are obtained in moderate to good yields under mild reaction conditions. The scope of the reaction is quite decent, allowing for the synthesis of disubstituted furans having aryl and heteroaromatic groups.

Palladium-catalyzed reductive homocoupling of aryl sulfonates via cleavage of C─O bond at room temperature

Palladium-catalyzed reductive homocoupling of aryl sulfonates has been successfully achieved under mild conditions. This transformation is a new method for the homocoupling reaction of aryl sulfonates at room temperature via the cleavage of C─O bonds, thus providing an alternative synthesis of symmetric biaryls. The reported reductive homocoupling reaction is tolerant of many common functional groups regardless of electron-donating or electron-withdrawing nature, making this newly developed transformation important for complementing Ullmann coupling. Experimental Section. Typical procedure for the products.

Bifurans via palladium-catalyzed Suzuki coupling

Sixteen 2,2'-bifurans with aryl substituents are reported. The copper-mediated oxidative coupling of lithium salt of furan led to the formation of 2,2'-bifuran, which was brominated with either 2 eq. or 4 eq. NBS to afford 5,5'-dibromo-2,2'-bifuran and 3,3',5,5'-tetrabromo-2,2'-bifuran. The palladiumcatalyzed Suzuki reactions between dibromo or tetrabormo-bifuran and arylboronic acid were employed to furnish the title compounds, which were characterized by NMR spectra and mass spectra.

Ligand-, base-, co-catalyst-free copper fluorapatite (CuFAP) as a versatile, ecofriendly, heterogeneous and reusable catalyst for an efficient homocoupling of arylboronic acid at ambient reaction conditions

This paper describes the first report in which copper species containing copper fluorapatite (CuFAP) acts as a versatile, eco-friendly, recyclable, heterogeneous catalyst for an efficient synthesis of symmetric biaryls from the homo-coupling of arylboronic acids in methanol solvent at ambient reaction conditions. The developed protocol is ligand-, base-, and co-catalyst-free, sustainable, mild, inexpensive, and compatible with a wide range of aromatic/heterocyclic boronic acids and provides the corresponding products in excellent yields without purification. The catalyst was easily recovered from the reaction mixture and reused several times without loss of activity.

Poly(mono-, bi- or trifuran): Effect of oligomer chain length on the electropolymerization performances and polymer properties

Most recently, oligo-/polyfurans have regained widely attention due to their unique properties and promising applications in organic electronics. Herein, to acquire a thorough fundamental understanding of the electrosynthesis and properties of polyfuran (PFu) from different initial oligomers, the synthesis, fluorescence, and electropolymerization performances of α-oligofurans, namely furan (Fu), bifuran (2Fu), trifuran (3Fu), were comprehensively reported and the effect of oligomer chain length on the structure and properties of the resulting PFu films were evaluated. The oligofurans introduced here revealed higher fluorescence efficiency (0.05 for Fu, 0.19 for 2Fu and 0.27 for 3Fu) than the corresponding oligothiophenes and oligoselenophenes. The onset oxidation potential of oligofurans decreased obviously (1.25 V for Fu, 0.8 V for 2Fu, and 0.7 V for 3Fu) with the chain length of the starting monomers increasing, thus leading to the electrodeposition of high quality free-standing PFu films with improved optoelectronic properties. Structure characterization and properties of the as-formed PFu from different initial oligomers, including FT-IR, UV-vis, surface morphology, fluorescence, electroactivity and stability, electrochromic properties, etc., were systematically investigated and comprehensively discussed.

Suzuki-Miyaura reactions of the soluble guanylate cyclase inhibitor NS2028: A non-product specific route to C-8 substituted analogues

Both soluble guanylate cyclase (sGC) inhibitors ODQ 1 and NS2028 2 are synthesized via improved protocols. In the former case treating 3,4-dihydroquinoxalin-2(1H)-one oxime 8, which can be prepared in two steps from 1,2-benzenediamine, with 1,1′-carbonyldiimidazole (CDI) gives the dihydro-ODQ 10 that in the presence of KMnO4 oxidises to give ODQ 1 in an overall yield of 46% starting from 1,2-benzenediamine. In the latter case, the synthesis affords NS2028 2 from 2-amino-4-bromophenol 3 in three steps with an overall yield of 85% and avoids the need for chromatography. Furthermore, Suzuki-Miyaura reaction conditions are described that enable the preparation of 8-aryl and 8-heteroaryl derivatives of NS2028 directly from NS2028 2. Finally, demethylation of the 8-(methoxyphenyl) substituted analogues afforded the 8-(hydroxyphenyl) derivatives 40-42. All new products are fully characterised.

Deprotonative metalation of substituted benzenes and heteroaromatics using amino/alkyl mixed lithium-zinc combinations

Different homoleptic and heteroleptic lithium-zinc combinations were prepared, and structural elements obtained on the basis of NMR spectroscopic experiments and DFT calculations. In light of their ability to metalate anisole, pathways were proposed to justify the synergy observed for some mixtures. The best basic mixtures were obtained either by combining ZnCl 2·TMEDA (TMEDA = N,N,N',N'tetramethylethylenediamine) with [Li(tmp)] (tmp = 2,2,6,6-tetramethylpiperidino; 3 equiv) or by replacing one of the tmp in the precedent mixture with an alkyl group. The reactivity of the aromatic lithium zincates supposedly formed was next studied, and proved to be substrate-, base-, and electrophile-dependent. The aromatic lithium zincates were finally involved in palladium-catalyzed cross-coupling reactions with aromatic chlorides and bromides.