51061-85-9

Basic information

• Product Name: 3-ETHYNYL-FURAN
• Synonyms: 3-ETHYNYL-FURAN
• CAS NO: 51061-85-9
• Molecular Formula: C₆H₄O
• Molecular Weight: 92.09536
• Mol File: 51061-85-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 104.591°C at 760 mmHg
• Flash Point: 10.846°C
• Appearance: /
• Density: 1.03g/cm³
• Vapor Pressure: 35.603mmHg at 25°C
• Refractive Index: 1.5
• CAS DataBase Reference: 3-ETHYNYL-FURAN(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ETHYNYL-FURAN(51061-85-9)
• EPA Substance Registry System: 3-ETHYNYL-FURAN(51061-85-9)

Safety Data

• Hazardous Substances Data: 51061-85-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 2473, 1983 DOI: 10.1016/S0040-4039(00)81958-9

InChI:InChI=1/C6H4O/c1-2-6-3-4-7-5-6/h1,3-5H

Upstream product

• 498-60-2 furan-3-carboxaldehyde 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 145397-30-4 C₈H₂₁N₄PSi 
• 86842-14-0 3-Trimethylsilanyl-4-trimethylsilanylethynyl-furan 

Downstream Products

• 6617-37-4 5Z-5-[E-5-(3-furanyl)-2-methyl-2-penten-4-yn-1-ylidene]-3-methyl-2(5H)-furanone 
• 97521-91-0 (4S,4aR,8S,8aS)-8-Benzyloxymethyl-4-furan-3-ylethynyl-4-hydroxy-3,4a-dimethyl-4a,5,8,8a-tetrahydro-4H-naphthalen-1-one 

Relevant articles and documents

Z-ore E-configurated γ-alkylidenebutenolides from a 2- (trimethylsiloxy)furan and iodomethacrolein - Stereoselective synthesis of Z- and E-freelingyne

The γ-(α-hydroxylalkyl)butenolides lk-5 and ul-5 were prepared by Mukaiyama aldol additions between iodoaldehyde 10 and the trimethylsiloxy-substituted furan 6 in the presence of BF3·OEt2 and ZnBr2, respectively. Couplings of these butenolides with 3- ethynylfuran followed by anti-eliminations of water mediated by DEAD/PPh3 led to Z-freelingyne (Z-11 dy = 92:8) anti E-freelingyne (E-11: ds = 98:2).

Reaction of C-silylated α-diazophosphines as nucleophiles toward carbonyl compounds: A mechanistic study and application to the synthesis of alkynes and α-hydroxyphosphonamides

Diversely substituted α-hydroxyphosphonamides and alkynes have been efficiently synthesized through the reaction of C-silylated α- diazophosphines with different types of aldehydes (2 equiv) in a neutral medium under very mild conditions. The reaction with some chiral aldehydes is highly diastereoselective leading to phosphonamides as single diastereomers. The novel reaction is influenced by electronic and steric effects being precluded for aromatic aldehydes containing electron-releasing substituents on the phenyl ring and for bulky aliphatic aldehydes. The mechanistic studies of these processes, which are highly exothermic, provide evidence for a nucleophilic attack of the diazophosphine to the aldehyde leading to a betaine that rapidly rearranges to a diazomethylenephosphorane, which has been detected or captured in some instances. The diazomethylenephosphorane reacts with a second molecule of aldehyde according to a Wittig-type condensation, and the rate-determining step of the whole process is believed to be the decomposition of the resultant oxaphosphetane to afford the hydroxyphosphonamide and a diazocumulene. Finally, this intermediate loses molecular nitrogen giving a transient carbene that rapidly evolves toward the alkyne.

Synthesis of polycylic aromatic heterocyclic compounds via thermal isomerizations of 1,8-diarylethynylnaphthalenes

The palladium catalyzed reaction between 1,8-diiodonaphthalene and ethynylarenes affords 1,8-Bis(heteroarylethynyl)naphthalenes which can cyclize thermally via diradical intermediates to the corresponding heterocyclic acenaphthene derivatives in high yiel