617-90-3

Basic information

• Product Name: 2-Furonitrile
• Synonyms: AKOS B004255;2-CYANOFURAN;2-FURANCARBONITRILE;2-FURONITRILE;BUTTPARK 96\57-57;FURAN-2-CARBONITRILE;2-Furyl cyanide;alpha-Furyl cyanide
• CAS NO: 617-90-3
• Molecular Formula: C₅H₃NO
• Molecular Weight: 93.08
• EINECS: 210-537-4
• Product Categories: Furan&Benzofuran
• Mol File: 617-90-3.mol

Chemical Properties

• Melting Point: 147-148 °C
• Boiling Point: 146-148 °C(lit.)
• Flash Point: 95 °F
• Appearance: Clear light yellow to light orange/Liquid
• Density: 1.064 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.98mmHg at 25°C
• Refractive Index: n20/D 1.479(lit.)
• Storage Temp.: Flammables area
• Water Solubility: Soluble in most common organic solvents. Slightly soluble in water.
• BRN: 107033
• CAS DataBase Reference: 2-Furonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Furonitrile(617-90-3)
• EPA Substance Registry System: 2-Furonitrile(617-90-3)

Safety Data

• Hazard Codes: Xn
• Statements: 10-20/21/22-41
• Safety Statements: 26-36/37/39-36/37-16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 617-90-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
2-Furonitrile is used as an extractive distillation solvent for the separation of closely boiling mixtures, particularly in the purification of organic compounds. Its selective solvation properties make it an effective agent in this application.
Used in Food Industry:
2-Furonitrile is used as a sweetening agent, providing a sweet taste to food products without contributing significant calories. This makes it a suitable alternative for sugar in certain applications, particularly for those seeking to reduce calorie intake.
Used in Pharmaceutical Industry:
2-Furonitrile is used as an intermediate in the synthesis of pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Fine Chemical Synthesis:
2-Furonitrile is utilized as an intermediate in the production of fine chemicals, which are high-purity chemicals used in various industries, including pharmaceuticals, agriculture, and materials science.
Used in Biotechnology Research:
2-Furonitrile was employed as a substrate to investigate the substrate specificity of nitrilase from Rhodococcus rhodochrous Jl cell. This research helps in understanding the enzymatic processes involved in the breakdown of nitrile compounds, which can be useful in developing biotechnological applications for the synthesis or degradation of specific organic compounds.

Synthesis Reference(s)

Synthesis, p. 472, 1983 DOI: 10.1055/s-1983-30387

InChI:InChI=1/C5H3NO/c6-4-5-2-1-3-7-5/h1-3H

Upstream product

• 123-91-1 1,4-dioxane 
• 110-00-9 furan 
• 506-68-3 bromocyane 
• 1121-47-7 2-furaldehyde oxime 
• 609-38-1 furan-2-carboxylic acid amide 
• 64-17-5 ethanol 
• 103-72-0 phenyl isothiocyanate 
• 620-03-1 furan-2-carbaldehyde oxime 
• 98-01-1 furfural 
• 76-02-8 trifluoroacetyl chloride 
• 527-69-5 2-furancarbonyl chloride 
• 6047-91-2 2-furoyl cyanide 
• 14064-21-2 2-furaldehyde dimethylhydrazone 
• 10530-89-9 2-ethanol 

Downstream Products

• 3194-17-0 1-furan-2-yl-pentan-1-one 
• 639086-73-0 [2]furyl-(3-methoxy-phenyl)-ketone 
• 4208-53-1 2-methyl-1-(2-furyl)-1-propanone 
• 14360-50-0 1-(furan-2-yl)hexan-1-one 
• 4685-18-1 2,4-diamino-6-(2-furyl)-1,3,5-triazine 
• 111609-50-8 cyclohexyl(furan-2-yl)methanone 
• 91136-66-2 (2,4-dihydroxy-phenyl)-[2]furyl ketone 
• 18240-50-1 bis((furan-2-yl)methyl)amine 
• 617-89-0 furan-2-ylmethanamine 
• 50892-99-4 N′-hydroxyfuran-2-carboximidamide 
• 49595-53-1 7-furan-2-yl-4,5-dimethyl-2-phenyl-2,3-dihydro-1H-[1,2]azaphosphepine 2-oxide 
• 59918-44-4 4-amino-3,5-di(2-furyl)-1,2,4-triazole 
• 59918-46-6 3,6-di-furan-2-yl-1,2⁽⁴⁾-dihydro-[1,2,4,5]tetrazine 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 

Relevant articles and documents

Preparation of Fluorescent Materials from Biomass-Derived Furfural and Natural Amino Acid Cysteine through Cross-Coupling Reactions for Extended π-Conjugation

Preparation of 2-furylthiazole-4-carboxylic acid methyl ester is achieved in four steps from biomass-derived heteroaromatic compound furfural and a natural amino acid l-cysteine. One-pot bromination and following palladium-catalyzed arylation with arylboronates of the thus obtained furylthiazole at the furan ring gives arylated furylthiazole in excellent yields. Further arylation at the C-H bond of the thiazole ring (5-position) in the presence of AgF as an additive leads to diaarylated furylthiazoles, which show strong photoluminescence. Homocoupling at the C-H bond of thiazole is also carried out with AgF to afford the corresponding further conjugated product composed of eight (hetero)aromatic rings.

A Molecular Iron-Based System for Divergent Bond Activation: Controlling the Reactivity of Aldehydes

The direct synthesis of amides and nitriles from readily available aldehyde precursors provides access to functional groups of major synthetic utility. To date, most reliable catalytic methods have typically been optimized to supply one product exclusively. Herein, we describe an approach centered on an operationally simple iron-based system that, depending on the reaction conditions, selectively addresses either the C=O or C-H bond of aldehydes. This way, two divergent reaction pathways can be opened to furnish both products in high yields and selectivities under mild reaction conditions. The catalyst system takes advantage of iron's dual reactivity capable of acting as (1) a Lewis acid and (2) a nitrene transfer platform to govern the aldehyde building block. The present transformation offers a rare control over the selectivity on the basis of the iron system's ionic nature. This approach expands the repertoire of protocols for amide and nitrile synthesis and shows that fine adjustments of the catalyst system's molecular environment can supply control over bond activation processes, thus providing easy access to various products from primary building blocks.

Highly Efficient Oxidative Cyanation of Aldehydes to Nitriles over Se,S,N-tri-Doped Hierarchically Porous Carbon Nanosheets

Oxidative cyanation of aldehydes provides a promising strategy for the cyanide-free synthesis of organic nitriles. Design of robust and cost-effective catalysts is the key for this route. Herein, we designed a series of Se,S,N-tri-doped carbon nanosheets with a hierarchical porous structure (denoted as Se,S,N-CNs-x, x represents the pyrolysis temperature). It was found that the obtained Se,S,N-CNs-1000 was very selective and efficient for oxidative cyanation of various aldehydes including those containing other oxidizable groups into the corresponding nitriles using ammonia as the nitrogen resource below 100 °C. Detailed investigations revealed that the excellent performance of Se,S,N-CNs-1000 originated mainly from the graphitic-N species with lower electron density and synergistic effect between the Se, S, N, and C in the catalyst. Besides, the hierarchically porous structure could also promote the reaction. Notably, the unique feature of this metal-free catalyst is that it tolerated other oxidizable groups, and showed no activity on further reaction of the products, thereby resulting in high selectivity. As far as we know, this is the first work for the synthesis of nitriles via oxidative cyanation of aldehydes over heterogeneous metal-free catalysts.

CuO-catalyzed conversion of arylacetic acids into aromatic nitriles with K4Fe(CN)6 as the nitrogen source

Readily available CuO was demonstrated to be effective as the catalyst for the conversion of arylacetic acids to aromatic nitriles with non-toxic and inexpensive K4Fe(CN)6 as the nitrogen source via the complete cleavage of the C[tbnd]N triple bond. The present method allowed a series of arylacetic acids including phenylacetic acids, naphthaleneacetic acids, 2-thiopheneacetic acid and 2-furanacetic acid to be converted into the targeted products in low to high yields.

Product selectivity controlled by manganese oxide crystals in catalytic ammoxidation

The performances of heterogeneous catalysts can be effectively tuned by changing the catalyst structures. Here we report a controllable nitrile synthesis from alcohol ammoxidation, where the nitrile hydration side reaction could be efficiently prevented by changing the manganese oxide catalysts. α-Mn2O3 based catalysts are highly selective for nitrile synthesis, but MnO2-based catalysts including α, β, γ, and δ phases favour the amide production from tandem ammoxidation and hydration steps. Multiple structural, kinetic, and spectroscopic investigations reveal that water decomposition is hindered on α-Mn2O3, thus to switch off the nitrile hydration. In addition, the selectivity-control feature of manganese oxide catalysts is mainly related to their crystalline nature rather than oxide morphology, although the morphological issue is usually regarded as a crucial factor in many reactions.

Method for catalyzing receptor-free dehydrogenation of primary amine to generate nitrile by Ru coordination compound

The invention discloses a method for catalyzing receptor-free dehydrogenation of primary amine to generate nitrile by a Ru coordination compound. The method comprises: adding a Ru coordination compound, an alkali, a primary amine and an organic solvent into a reaction test tube according to a mol ratio of 1:100:(100-500):1000-3000, and carrying out a stirring reaction under the condition of 80 to120 DEG C; and when gas chromatography monitors that the raw materials completely disappear, stopping the reaction, collecting the reaction solution, centrifuging the reaction solution, taking the supernatant, extracting with dichloromethane, merging the organic phases, drying, filtering, evaporating the organic solvent under reduced pressure to obtain a filtrate, and carrying out column chromatography purification on the filtrate to obtain the target product nitrile. According to the invention, the catalyst is good in activity, single in catalytic system, good in product selectivity, simple in subsequent treatment and good in system universality after the reaction is finished, has a good catalytic effect on various aryl, alkyl and heteroaryl substituted primary amines, and also has a gooddehydrogenation performance on secondary amines.

Integrating Biomass into the Organonitrogen Chemical Supply Chain: Production of Pyrrole and d-Proline from Furfural

Production of renewable, high-value N-containing chemicals from lignocellulose will expand product diversity and increase the economic competitiveness of the biorefinery. Herein, we report a single-step conversion of furfural to pyrrole in 75 % yield as a key N-containing building block, achieved via tandem decarbonylation–amination reactions over tailor-designed Pd?S-1 and H-beta zeolite catalytic system. Pyrrole was further transformed into dl-proline in two steps following carboxylation with CO2 and hydrogenation over Rh/C catalyst. After treating with Escherichia coli, valuable d-proline was obtained in theoretically maximum yield (50 %) bearing 99 % ee. The report here establishes a route bridging commercial commodity feedstock from biomass with high-value organonitrogen chemicals through pyrrole as a hub molecule.

Iron-Promoted Decarboxylation of Arylacetic Acids for the Synthesis of Aromatic Nitriles with Sodium Nitrite as the Nitrogen Source

A new and effective method was developed for the synthesis of aromatic nitriles from arylacetic acids by using NaNO 2as the nitrogen source and Fe(OTf) 3as the promoter at 50 °C. A series of arylacetic acids underwent this transformation to give the targeted products in yields of 51-90%. Because of the mild conditions, the reaction is compatible with a broad range of functional groups, including ester, carboxy, hydroxy, acetamido, halo, nitro, cyano, methoxy, and even highly reactive formyl groups.

Atomically Dispersed Ru on Manganese Oxide Catalyst Boosts Oxidative Cyanation

There is a strong incentive for environmentally benign and sustainable production of organic nitriles to avoid the use of toxic cyanides. Here we report that manganese oxide nanorod-supported single-site Ru catalysts are active, selective, and stable for oxidative cyanation of various alcohols to give the corresponding nitriles with molecular oxygen and ammonia as the reactants. The very low amount of Ru (0.1 wt %) with atomic dispersion boosts the catalytic performance of manganese oxides. Experimental and theoretical results show how the Ru sites enhance the ammonia resistance of the catalyst, bolstering its performance in alcohol dehydrogenation and oxygen activation, the key steps in the oxidative cyanation. This investigation demonstrates the high efficiency of a single-site Ru catalyst for nitrile production.

Earth-Abundant Bimetallic Nanoparticle Catalysts for Aerobic Ammoxidation of Alcohols to Nitriles

Heterogeneous nitrogen-doped carbon-incarcerated iron/copper bimetallic nanoparticle (NP) catalysts prepared from nitrogen-containing polymers were developed. These catalysts showed activity higher than that of the corresponding monometallic NPs for aerobic ammoxidation of alcohols to nitriles. The important procedure for high activity in the catalyst preparation was found to be a simultaneous reduction of two metal salts.