76537-07-0

Basic information

• Product Name: Furan, 2-isocyanato-
• Synonyms: 2-furanylisocyanate;furfuryl isocyanate;2-furoyl isocyanate;Furan,2-isocyanato;2-isocyanato-furan;2-furyl isocyanate
• CAS NO: 76537-07-0
• Molecular Formula: C5H3NO2
• Molecular Weight: 109.084
• Mol File: 76537-07-0.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Furan, 2-isocyanato-(CAS DataBase Reference)
• NIST Chemistry Reference: Furan, 2-isocyanato-(76537-07-0)
• EPA Substance Registry System: Furan, 2-isocyanato-(76537-07-0)

Safety Data

• Hazardous Substances Data: 76537-07-0(Hazardous Substances Data)

Upstream product

• 17698-14-5 furan-2-carboxylic acid hydroxyamide 
• 4340-42-5 2-furoyl isocyanate 
• 77219-91-1 C₁₁H₂₁NO₃Si₂ 
• 20762-98-5 2-furoyl azide 

Downstream Products

• 1282521-19-0 N-(9-fluorenylmethoxycarbonyl)-N'-(2-furyl)-L-phenylalaninamide 
• 480993-89-3 [4-(2,3,4,5-tetrahydro-1,3-dimethyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-6-yl)phenyl]methyl furan-2-ylcarbamate 
• 1028991-98-1 4-((4-chlorophenyl)(2,4-dichlorophenyl)methyl)-N-(furan-2-yl)piperazine-1-carboxamide 
• 226710-95-8 hex-4-enoic acid furan-2-yl(4-methoxybenzyl)amide 
• 226710-98-1 N-(furan-2-yl)-2-vinylbenzamide 
• 139210-18-7 (E)-3-[2-(Furan-2-yliminomethyleneamino)-phenyl]-acrylic acid ethyl ester 
• 139210-17-6 (E)-3-[2-(Furan-2-yliminomethyleneamino)-phenyl]-acrylic acid methyl ester 

Relevant articles and documents

Ruthenium(II)-Catalyzed Regioselective Ortho Amidation of Imidazo Heterocycles with Isocyanates

Direct ortho amidation at the phenyl ring of 2-phenylimidazo heterocycles with aryl isocyanates has been achieved via a chelation-assisted cationic ruthenium(II) complex catalyzed mechanism. The methodology provides a straightforward, high-yielding regios

Eight-Step Enantioselective Total Synthesis of (?)-Cycloclavine

The first enantioselective total synthesis of (?)-cycloclavine was accomplished in 8 steps and 7.1 % overall yield. Key features include the first catalytic asymmetric cyclopropanation of allene, mediated by the dirhodium catalyst Rh2(S-TBPTTL)4, and the enone 1,2-addition of a new TEMPO carbamate methyl carbanion. An intramolecular strain-promoted Diels–Alder methylenecyclopropane (IMDAMC) reaction provided a pivotal tricyclic enone intermediate with more than 99 % ee after crystallization. The synthesis of (?)-1 was completed by a late-stage intramolecular Diels–Alder furan (IMDAF) cycloaddition to install the indole.

A Cycloaddition Approach toward the Synthesis of Substituted Indolines and Tetrahydroquinolines

The intramolecular Diels-Alder reaction of 2-substituted aminofurans (IMDAF) results in the formation of various indolines and tetrahydroquinolines. The isolation of these ring systems from the IMDAF reaction can be rationalized in terms of an initial [4 + 2]-cycloaddition that first produces an oxa-bridged cycloadduct, which was not detected since it readily underwent nitrogen-assisted ring opening. Proton exchange followed by an eventual dehydration provides the aromatic product. In certain cases, the intermediate cyclohexadienol can be isolated and independently converted to the final product in high yield. The starting 2-aminofurans were readily prepared from furanyl acyl azide by a Curtius rearrangement in the presence of an alcohol. Alkylation of the resulting N-alkyl carbamate with an alkenyl bromide allows for the synthesis of a wide variety of cycloaddition precursors. The scope of the IMDAF reaction was evaluated by using mono- and disubstituted alkenes, electron rich and electron deficient olefins, and acetylenic tethers. Cyclic 2-amidofurans were also synthesized using a related intramolecular Diels-Alder reaction of 2-amido-substituted oxazoles which contain a tethered alkyne. This transformation represents a new route to this rare heterocyclic ring system. The sequential cycloaddition method was used for a formal synthesis of the pyrrolophenanthridone alkaloid hippadine.