14920-89-9

Usage

Uses

1. Used in the Synthesis of 2,9-dioxabicyclo[3.3.1]nonane:
2,3-Dimethylfuran is used as a key intermediate in the synthesis of 2,9-dioxabicyclo[3.3.1]nonane, a compound with potential applications in various chemical and pharmaceutical industries.
2. Used in the Synthesis of Ireland Alcohol:
2,3-Dimethylfuran is also utilized in the synthesis of Ireland alcohol, which is an important building block in the preparation of various organic compounds and pharmaceuticals.
3. Used in the Chemical Industry:
As a versatile organic compound, 2,3-dimethylfuran can be used in the chemical industry for the production of various chemicals, materials, and intermediates.
4. Used in the Pharmaceutical Industry:
Due to its unique chemical structure, 2,3-dimethylfuran may have potential applications in the pharmaceutical industry as a starting material for the synthesis of novel drug candidates or as a component in drug delivery systems.
5. Used in the Flavor and Fragrance Industry:
Given its furan-based structure, 2,3-dimethylfuran may also find applications in the flavor and fragrance industry, where furan derivatives are often used to create specific scents and flavors.

Synthesis Reference(s)

Synthetic Communications, 20, p. 1113, 1990 DOI: 10.1080/00397919008052818

InChI:InChI=1/C6H8O/c1-5-3-4-7-6(5)2/h3-4H,1-2H3

Upstream product

• 89639-83-8 4,5-dimethyl-furan-2-carboxylic acid 
• 534-22-5 2-methylfuran 
• 593-53-3 Methyl fluoride 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 6153-05-5 (Z)-3-methylpent-2-en-4-ynol 
• 201230-82-2 carbon monoxide 
• 6153-06-6 3-methylpent-2-en-4-yn-1-ol 
• 99088-37-6 5-(trimethylsilyl)-3-methyl-3-penten-4-yn-1-ol 
• 98490-89-2 methyl 4-(chloromethyl)-5-methylfuran-2-carboxylate 
• 2527-96-0 methyl 5-methyl-2-furancarboxylate 
• 61834-24-0 methyl 4,5-dimethylfuran-2-carboxylate 
• 111301-75-8 dimethyl 4,5-dimethylfuran-2,3-dicarboxylate 
• 6141-58-8 methyl 2-methyl-3-furancarboxylate 

Downstream Products

• 73761-44-1 2-acetyl-4,5-dimethylfuran 
• 119155-04-3 ethyl 4,5-dimethylfuroate 
• 85828-13-3 (1S,2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-dimethyl-furan-2-yl)-2,4-dimethyl-pentan-1-ol 
• 85880-74-6 (1R,2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-dimethyl-furan-2-yl)-2,4-dimethyl-pentan-1-ol 
• 25234-83-7 methyl 3-methyl-4-oxopentanoate 
• 29745-04-8 norcantharidin 
• 1253045-04-3 SnI(CH₂C₄H₂O(CH₃))(C(SiMe₃)2CH₂CH₂C(SiMe₃)2) 
• 1253045-05-4 SnI(CH₂C₄H₂O(CH₃))(C(SiMe₃)2CH₂CH₂C(SiMe₃)2) 
• 1253044-88-0 SnI(C₆H₂(iPr)3)(C(SiMe₃)2CH₂CH₂C(SiMe₃)2) 
• 1014736-53-8 SnI(Ph)(C(SiMe₃)2CH₂CH₂C(SiMe₃)2) 
• 1253045-07-6 SnI(C₆H₂Me₃)(C(SiMe₃)2CH₂CH₂C(SiMe₃)2) 
• 1073338-90-5 4,4,5,5-tetramethyl-2-(4,5-dimethylfuran-2-yl)-1,3,2-dioxaborolane 
• 1259937-64-8 trans-2,3-dimethyl-5-styryl furan 
• 1422191-49-8 (E)-5-(4-chlorostyryl)-2,3-dimethylfuran 

Relevant academic research and scientific papers

A new and efficient synthesis of rosefuran. A general synthesis of furans by palladium-catalysed cycloisomerization of (Z)-2-en-4-yn-1-ols

(Z)-3,7-Dimethylocta-2,6-dien-4-yn-1-ol, readily available from (Z)-3-methylpent-2-en-4-yn-1-ol, undergoes cycloisomerization in the presence of catalytic amounts of K2PdI4 to give rosefuran in high yield.

Novel ruthenium-catalysed synthesis of furan derivatives via intramolecular cyclization of hydroxy enynes

Furans containing a functional group at C(5) are obtained under neutral conditions by selective cyclization of (Z)-pent-2-en-4-yn-1-ols in the presence of RuCl2(PPh3)(p-cymene) as catalyst precursor.

Synthesis and characterization of 1′-(diphenylphosphino)-1-isocyanoferrocene, an organometallic ligand combining two different soft donor moieties, and its Group 11 metal complexes

The development of a practical synthesis of 1′-(diphenylphosphino)-1-aminoferrocene (2) and its P-borane adduct (2B) allowed the facile preparation of 1′-(diphenylphosphino)-1-isocyanoferrocene (1). This compound combining two specific soft-donor moieties was studied as a ligand for univalent Group 11 metal ions. The reactions of 1 with AgCl at 1:1 and 2:1 molar ratios only led to the coordination polymer [Ag2(μ-Cl)2(μ(P,C)-1)]n (6), while those with Ag[SbF6] provided the dimer [Ag2(Me2CO-κO)2(μ(P,C)-1)2][SbF6]2 and the quadruply-bridged disilver complex [Ag2(μ(P,C)-1)4][SbF6]2 (8), respectively. Addition of 1 to [AuCl(tht)] (tht = tetrahydrothiophene) afforded the mono- and the digold complex, [AuCl(1-κP)] (9) and [(μ(P,C)-1)(AuCl)2] (10), depending on the reaction stoichiometry. Finally, the reaction of 1 with [Au(tht)2][SbF6] or halogenide removal from 9 with AgNTf2 led to cationic dimers [Au2(μ(P,C)-1)2]X2 (11, X = SbF6 (a) or NTf2 (b)). Catalytic tests in the Au-mediated isomerization of (Z)-3-methylpent-2-en-4-yn-1-ol to 2,3-dimethylfuran revealed that 11a and 11b are substantially less catalytically active than their analogues containing 1′-(diphenylphosphino)-1-cyanoferrocene as the ligand, most likely due to a stronger coordination of the isonitrile moiety, which prevents dissociation of the dimeric complexes into catalytically active monomeric species.

Palladium-catalyzed cycloisomerization of (Z)-enynols into furans using green solvents: Glycerol vs. water

Heteroannulation reactions of (Z)-2-en-4-yn-1-ol derivatives into furans can be conveniently performed in water and glycerol using cis-[PdCl 2(DAPTA)2] as catalyst. Higher activities were observed in an aqueous medium, but catalyst r

Gas-phase Alkylation of 2-Methylfuran under Chemical Ionization Conditions

In the gas phase, under chemical ionization conditions, the sites of attachment of + and + to 2-methylfuran have been studied by tandem mass spectrometry.Spontaneous metastable and collision-induced fragmentations have been compared to those observed for the protonated alkylfuran isomers.The results obtained show that alkylation occurs preferentially at the β-position.

Benzimidazole, benzothiazole and benzoxazole ruthenium(II) complexes; catalytic synthesis of 2,3-dimethylfuran

Fourteen ruthenium(II) complexes of the type [RuCl2(η6-arene)L], (arene = 1,4-MeC6H4Pr(i) or C6Me6; L = benzimidazole derivative in which the NH group is substituted by N-alkyl or isoelectronic O or S atoms) have been prepared by cleavage of [RuCl2(η6-arene)]2 with the N-heterocycle L. Their spectroscopic and electrochemical properties are described. The effect of the nature of the benzazole (L) on the catalytic activity of these complexes for the intramolecular cyclization of (Z)-3-methylpent-2-en-4-yn-1- ol into 2,3-dimethylfuran has also been studied; the benzimidazole complexes were found to be the most active.

Octahedral ruthenium(II) complexes cis,cis-[RuX2(CNR)(CO)(P∧P)] and cis,cis,cis-[RuX2(CO)2(P∧P)] (X = Cl, Br; P∧P = 1,1′-bis(diphenylphosphino)ferrocene, 1,1′-bis(diisopropylphosphino)ferrocene): Synthesis and catalytic applications in transfer hydrogenation of acetophenone and cycloisomerization of...

Full title: Octahedral ruthenium(II) complexes cis,cis-[RuX2(CNR)(CO)(P∧P)] and cis,cis,cis-[RuX2(CO)2(P∧P)] (X = Cl, Br; P∧P = 1,1′-bis(diphenylphosphino)ferrocene, 1,1′-bis(diisopropylphosphino)ferrocene): Synthesis and catalytic applications in transfer hydrogenation of acetophenone and cycloisomerization of (Z)-3-methylpent-2-en-4-yn-1-ol. Carbonyl-isocyanide-ruthenium(II) complexes cis,cis-[RuX2(CNR)(CO)(P∧P)] (P∧P = dppf, dippf; X = Cl, Br; R = Bn, Cy, tBu, 2,6-C6H3Me2, (S)-(-)-C(H)MePh) (3-6a-e) have been prepared in high yields by treatment of the dimeric derivatives [{RuX(μ-X)(CO)(P∧P)}2] (P∧P = dppf, dippf; X = Cl, Br) (1-2a-b) with isocyanides. Dimers 1-2a-b also react with carbon monoxide to afford the dicarbonyl species cis,cis,cis-[RuX2(CO)2(P∧P)] (7-8a-b). The catalytic activity of these compounds in transfer hydrogenation of acetophenone by propan-2-ol as well as in cycloisomerization of (Z)-3-methylpent-2-en-4-yn-1-ol into 2,3-dimethylfuran has been studied.

CYCLOADDITION REACTIONS OF POLYSUBSTITUTED FURANS WITH OXYALLYL CARBOCATIONS

New and improved routes to polysubstituted furans are described, together with a survey of their reactivity in cycloaddition reactions with oxyallyl carbocations, producing polysubstituted 8-oxabicyclooct-6-3-ones.

Novel synthesis of furan-2-acetic esters by palladium-catalysed oxidative cyclization-alkoxycarbonylation of (Z)-2-En-4-yn-1-ols

Furan-2-acetic esters are obtained in good yields by direct oxidative cyclization-alkoxycarbonylation lation of (Z)-2-en-4-yn-1-ols. bearing both an alkyl or an aryl substituent a to the hydroxy group. in the presence of catalytic amounts of palladium iod

Synthesis, Reactivity, and Coordination of Semihomologous dppf Congeners Bearing Primary Phosphine and Primary Phosphine Oxide Groups

This contribution reports the synthesis of two phosphinoferrocene ligands desymmetrized by an inserted methylene spacer, viz., a bis-phosphine combining primary and tertiary phosphine moieties in its structure, Ph2PfcCH2PH2 (2), and a structurally unique, stable phosphine-primary phosphine oxide Ph2PfcCH2P(O)H2 (7; fc = ferrocene-1,1′-diyl). Compounds 2 and 7, together with 1,1′-bis(diphenylphosphino)ferrocene (dppf), the bis-tertiary phosphine Ph2PfcCH2PPh2, and the adduct Ph2P(BH3)fcCH2PH2 (6), were studied as ligands in Ru(II) complexes bearing auxiliary ν6-arene ligands and both free ligands and the isolated complexes were structurally authenticated, using spectroscopic methods and X-ray crystallography, and further investigated by cyclic voltammetry. The results suggest that distinct donor moieties in the unsymmetric ligands differentiate the otherwise identical coordinated metal centers and that the phosphine moiety in phosphine-phosphine oxide ligand 7 is preferably coordinated to Ru(II), before the phosphine oxide group, which must tautomerize into the hydroxyphosphine form prior to coordination.