89149-70-2

Usage

Uses

Used in Pharmaceutical Industry:
5-(Hydroxymethyl)furan-2-carbonitrile is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of novel drug molecules. Its unique structure allows for the creation of a wide range of therapeutic agents, enhancing the industry's capacity to address various health conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 5-(Hydroxymethyl)furan-2-carbonitrile is utilized as a building block for the synthesis of agrochemicals, such as pesticides and herbicides. Its incorporation into these products aids in the development of more effective and targeted solutions for agricultural challenges.
Used in Fine Chemicals Production:
5-(Hydroxymethyl)furan-2-carbonitrile serves as an intermediate in the production of fine chemicals, which are high-purity chemicals used in various applications, including the synthesis of pharmaceuticals, fragrances, and flavors. Its role in this process is crucial for achieving the desired purity and functionality of the final products.
Used in Dyes Industry:
5-(HYDROXYMETHYL)FURAN-2-CARBONITRILE is also used in the synthesis of dyes, where its unique properties contribute to the development of new dye molecules with specific color characteristics and application properties. Its versatility in this field allows for the creation of dyes for various industries, such as textiles, plastics, and printing inks.
Used in Material Science:
5-(Hydroxymethyl)furan-2-carbonitrile has potential applications in the field of material science, where its properties can be harnessed to develop new materials with specific characteristics, such as improved strength, flexibility, or chemical resistance.
Used as a Reagent in Organic Chemistry:
In organic chemistry, 5-(Hydroxymethyl)furan-2-carbonitrile is employed as a reagent, facilitating various chemical reactions and synthesis processes. Its presence in these reactions can enhance the efficiency and selectivity of the processes, leading to the production of desired organic compounds.
It is important to handle and store 5-(Hydroxymethyl)furan-2-carbonitrile with care, as it may pose hazards to human health and the environment if not properly managed. Proper safety measures and storage conditions are essential to mitigate any potential risks associated with 5-(HYDROXYMETHYL)FURAN-2-CARBONITRILE.

InChI:InChI=1/C6H5NO2/c7-3-5-1-2-6(4-8)9-5/h1-2,8H,4H2

Upstream product

• 98-00-0 (2-furyl)methyl alcohol 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 89149-68-8 2-cyano-5-furfuryl acetate 
• 42061-89-2 5-cyano-2-furancarboxaldehyde 
• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 617-90-3 2-furancarbonitrile 
• 623-17-6 furfurylacetate 
• 60838-00-8 5-cyano-furan-2-carboxylic acid methyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 67-56-1 methanol 
• 823-82-5 2,5-diformylfurane 
• 5985-31-9 (E)-5-(hydroxymethyl)furan-2-carbaldehyde oxime 
• 57-48-7 fructose 
• 57-48-7 D-Fructose 

Downstream Products

• 89149-72-4 5-(hydroxymethyl)furan-2-carboxamide 
• 42061-89-2 5-cyano-2-furancarboxaldehyde 
• 148759-25-5 5-(bromomethyl)furan-2-carbonitrile 
• 1027236-11-8 C₂₆H₂₇N₅O₅S 
• 203792-32-9 5-aminomethyl-furan-2-carbonitrile; hydrochloride 

Relevant academic research and scientific papers

Exploring the Electronic Properties of Extended Benzofuran-Cyanovinyl Derivatives Obtained from Lignocellulosic and Carbohydrate Platforms Raw Materials

Two series of linear extended benzofuran derivatives associating cyanovinyl unit and phenyl or furan moieties obtained from benzaldehyde-lignocellulosic (Be series) or furaldehyde –saccharide (Fu series) platforms were prepared in order to investigate their emission and electrochemical properties. For the fluorescence in solution and solid states, contrasting results between the two series were demonstrated. For Be series a net aggregation induced emission effect was observed with high fluorescence quantum yield for the solid state. A [2+2] cycloaddition under irradiation at 350 nm was also revealed for one derivative of Be series. In contrast, for Fu series the fluorescence in solution is higher than in the solid state. The X-ray crystallography studies for the compounds reveal the formation of strong π-π stacking for the derivatives without emissive property in the solid state and the presence of essentially lateral contacts for emissive compounds. Taking advantage of the propensity to develop 2D π-stacking mode for the more extended derivative with a central furan cycle, organic field effect transistors presenting hole mobility have been made.

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.

Metabolically stable 5-HMF derivatives for the treatment of hypoxia

5-HMF derivative compounds that bind covalently with hemoglobin are provided. Methods of treating sickle cell disease and other hypoxia-related disorders by administering such compounds are also provided.

Method for preparing 5-hydroxymethyl-2-furannitrile through catalytic ammoxidation

The invention belongs to the organic synthesis field and particularly relates to a method for preparing 5-hydroxymethyl-2-furannitrile through catalytic ammoxidation. The method comprises the steps ofcarrying out ammoxidation reaction under the effect of a catalyst by taking 5-hydroxymethyl furfural as the raw material, one or two of oxygen or air as an oxidant and one or at least two of liquid ammonia, ammonia water or ammonia salt as a nitrogen source, carrying out centrifugation so as to remove the catalyst, carrying out rotary evaporation so as to remove a solvent, and carrying out purification by virtue of a column chromatography, so as to obtain a 5-hydroxymethyl-2-furannitrile product. The product of the method is high in yield and easy to separate and has very good application prospects.

Catalytic Amidation of 5-Hydroxymethylfurfural to 2,5-Furandicarboxamide over Alkali Manganese Oxides

2,5-Furandicarboxamide was firstly synthesized in yield of 85% via catalytic oxidative amidation of 5-hydroxymethylfurfural with aqueous NH3 over alkali manganese oxides of α-MnO2/NaxMnO2. The intermediates of 5-hydroxymethyl-furonitrile, 2,5-dicyanofuran, and 5-cyano-2-furancarboxamide were verified and their reactivities were further examined. The kinetic analysis results showed that the transformation of intermediate product of 5-cyano-2-furancarboxamide to 2,5-furan-dicarboxamide is a slower step, which is closely relative to the reaction temperature and basicity of catalyst.

Catalytic conversion of 5-hydroxymethylfurfural into 2,5-furandiamidine dihydrochloride

Via implantation of nitrogen from aq. NH3 into hydroxymethylfurfural (HMF), dimethyl furan-2,5-dicarboximidate was synthesized over a manganese oxide catalyst. It was realized by the ammoxidation of HMF followed by methanol addition under mild reaction conditions. The imidate prepared in situ was further transformed into 2,5-furandiamidine dihydrochloride by reaction with ammonium chloride.

Design and synthesis of a series of melamine-based nitroheterocycles with activity against trypanosomatid parasites

The parasites that give rise to human African trypanosomiasis (HAT) are auxotrophs for various nutrients from the human host, including purines. They have specialist nucleoside transporters to import these metabolites. In addition to uptake of purine nucleobases and purine nucleosides, one of these transporters, the P2 transporter, can carry melamine derivatives; these derivatives are not substrates for the corresponding mammalian transporters. In this paper, we report the coupling of the melamine moiety to selected nitro heterocycles with the aim of selectively delivering these compounds to the parasites. Some compounds prepared have similar in vitro trypanocidal activities as melarsoprol, the principal drug used against late-stage HAT, with 50% growth inhibitory concentrations in the submicromolar range. Selected compounds were also evaluated in vivo in rodent models infected with Trypanosoma brucei brucei and T. brucei rhodesiense and showed pronounced activity and in two cases were curative without overt signs of toxicity. Compounds were also tested against other trypanosomatid pathogens, Leishmania donovani and Trypanosoma cruzi, and significant activity in vitro was noted for T. cruzi against which various nitro heterocycles are already registered for use.

Efficacious and orally bioavailable thrombin inhibitors based on a 2,5-thienylamidine at the P1 position: Discovery of N-carboxymethyl-D-diphenylalanyl-L-prolyl[(5-amidino-2- thienyl)methyllamide

Thrombin, a crucial enzyme in the blood coagulation, has been a target for antithrombotic therapy. Orally active thrombin inhibitors would provide effective and safe prophylaxis for venous and arterial thrombosis. We conducted optimization of a highly efficacious benzamidine-based thrombin inhibitor LB30812 (3, Ki = 3 pM) to improve oral bioavailability. Of a variety of arylamidines investigated at the P1 position, 2,5-thienylamidine effectively replaced the benzamidine without compromising the thrombin inhibitory potency and oral absorption. The sulfamide and sulfonamide derivatization at the N-terminal position in general afforded highly potent thrombin inhibitors but with moderate oral absorption, while the well-absorbable N-carbamate derivatives exhibited limited metabolic stability in S9 fractions. The present work culminated in the discovery of the N-carboxymethyl- and 2,5-thienylamidine-containing compound 22 that exhibits the most favorable profiles of anticoagulant and antithrombotic activities as well as oral bioavilability (Ki = 15 pM; F = 43%, 42%, and 15% in rats, dogs, and monkeys, respectively). This compound on a gravimetric basis was shown to be more effective than a low molecular weight heparin, enoxaparin, in the venous thrombosis models of rat and rabbit. Compound 22 (LB30870) was therefore selected for further preclinical and clinical development.

INHIBITORS OF FARNESYL-PROTEIN TRANSFERASE

The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras.

Pyrethroid esters

A compound in all possible stereoisomeric forms and mixtures thereof of the formula STR1 wherein the substituents are defined as in the specification having pesticidal properties.