4915-06-4

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromo-2-furonitrile is utilized as a key intermediate in the synthesis of pyrimidines, which are integral components of numerous drugs and biologically active compounds. Its role in the creation of these essential building blocks underscores its importance in the development of new pharmaceuticals with diverse therapeutic applications.
Used in Agrochemical Industry:
In addition to its pharmaceutical applications, 5-Bromo-2-furonitrile also serves as a fundamental building block in the preparation of various agrochemicals. Its incorporation into the development of these compounds highlights its multifaceted utility in enhancing agricultural productivity and crop protection.
Organic Synthesis:
5-Bromo-2-furonitrile is employed as a versatile building block in organic synthesis, where its unique structure and reactivity contribute to the creation of a wide array of chemical entities. This makes it an indispensable component in the advancement of chemical research and the discovery of novel compounds with potential applications across various industries.

Upstream product

• 1899-24-7 5-bromo-2-furancarboxaldehyde 
• 67-56-1 methanol 
• 585-70-6 5-bromo-furan-2-carboxylic acid 
• 6134-61-8 5-bromo-furan-2-carboxylic acid amide 
• 4465-70-7 5-bromofurfural (E)-oxime 

Downstream Products

• 1899-24-7 5-bromo-2-furancarboxaldehyde 
• 2639446-16-3 5-(dimethylphosphoryl)furan-2-carbonitrile 

Relevant academic research and scientific papers

Synthesis and biological evaluation of novel marine-derived indole-based 1,2,4-oxadiazoles derivatives as multifunctional neuroprotective agents

Phidianidines (1), isolated from the marine opisthobranch mollusk Phidiana militaris, present the first example of natural products possessing an 1,2,4-oxadiazole ring system and show various bioactivities. However, the structure-activity relationship stu

A practical iodine-catalyzed oxidative conversion of aldehydes to nitriles

A simple and efficient method for the direct synthesis of nitriles from aldehydes using ammonium acetate as the nitrogen source has been developed. The reactions were performed with iodine as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant under mild conditions. A variety of aromatic, heteroaromatic, aliphatic and allylic aldehydes could be converted into their corresponding nitriles in good to excellent yields.

Electrocatalytic synthesis of nitriles from aldehydes with ammonium acetate as the nitrogen source

A simple synthesis method of nitriles from corresponding aldehydes by electrochemical oxidation was developed with ammonium acetate as the nitrogen source and 4-acetamido- 2,2,6,6-tetramethylpiperidinyl-l-oxy (4-AcNH-TEMPO) as the catalyst. Cyclic voltammetry was performed to investigate the electrocatalytic activity of 4-AcNH-TEMPO for the conversion of benzaldehyde to benzonitrile. On the basis of in situ FTIR data and cyclic voltammetry experiments, a reaction mechanism, involving the redox of 4-AcNH-TEMPO and the generation of intermediate imine during the reaction, was proposed. This electrocatalytic reaction system provided an efficient protocol for synthesis of aromatic nitriles at room temperature with moderate to high yields.

Catalytic and oxidizing synthetic method of nitriles compound

The invention discloses a catalytic and oxidizing synthetic method of a nitriles compound. The catalytic and oxidizing synthetic method comprises the following steps: adding reaction substrate aldehyde, NH4OAc, alkaline additives, I2 and TBHP (tert-butyl hydroperoxide) into an ethanol solvent, facilitating the reaction for 3 to 17 h at 40 to 60 DEG C, adding a sodium thiosulfate solution into a reaction solution, stirring, extracting with diethyl ether, separating to obtain an organic layer, decompressing and steaming to remove the solvent, performing the column chromatography isolation, adopting a mixed solution of ethyl acetate/petroleum ether in a volume ratio of 1: 100 as an eluent, collecting an elution solution containing a target compound, and steaming to remove the solvent, thus obtaining the product nitriles, wherein a weight ratio of the reaction substrate aldehyde to the alkaline additives to NH4OAc to I2 to TBHP is 100: (100 to 120): (120 to 160): (2 to 3): (100 to 120). The synthetic method has the beneficial effects that the operation is simple and safe, and the reaction condition is relatively moderate; and the reaction substrate is wide in application range.

IMIDAZO [1,5-A]PYRIMIDINYL CARBOXAMIDE COMPOUNDS AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS

The invention provides substituted imidazo[1,5-a]pyrimidinyl carboxamide and related organic compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat medical disorders, e.g., Gaucher disease, Parkinson's disease, Lewy body disease, dementia, or multiple system atrophy, in a patient. Exemplary substituted imidazo[1,5-a]pyrimidinyl carboxamide compounds described herein include substituted 2-heterocyclyl-4-alkyl-imidazo[1,5-a]pyrirnidine-8-carboxamide compounds and variants thereof.

A Mild TEMPO-Catalyzed Aerobic Oxidative Conversion of Aldehydes into Nitriles

An efficient method to prepare nitriles from aldehydes using hexamethyldisilazane (HMDS) as the nitrogen source has been developed. The reactions were performed with 2,2,6,6-tetramethylpiperidine l-oxyl (TEMPO) as the catalyst, NaNO2 or TBN as the co-catalyst, and molecular oxygen as the terminal oxidant under mild conditions. A variety of aromatic, heteroaromatic, aliphatic and allylic aldehydes could be converted into their corresponding nitriles in good to excellent yields.

Electrochemical synthesis of nitriles from aldehydes using TEMPO as a mediator

A novel electrochemical route to generate nitriles from aldehydes under mild conditions using a catalytic amount of TEMPO (2,2,6,6-tetramethylpiperidinyl-l-oxy) as the mediator and hexamethyldisilazane as the nitrogen source in the presence of acetic acid has been developed. A variety of aromatic, heteroaromatic and aliphatic aldehydes have been converted to their corresponding nitriles in good to excellent yields. A plausible reaction mechanism is proposed based on the cyclic voltammetry, in situ FTIR and the identification of intermediates.

Alkali α-MnO2/Na: XMnO2 collaboratively catalyzed ammoxidation-Pinner tandem reaction of aldehydes

The tandem reaction is a growing field to yield important advances toward green and sustainable chemistry. Herein, we report a bifunctional manganese oxide catalyst with an interface binding redox phase (α-MnO2) and a basic phase (NaxMnO2). The molar ratio of NaOH/Mn plays a great role in the formation of α-MnO2/NaxMnO2. The sodium cation is essential for the formation of a basic NaxMnO2 phase while the potassium cation promotes the formation of a redox-active α-MnO2 phase. The interface structure of α-MnO2/NaxMnO2 geometrically favors the ammoxidation-Pinner tandem reaction to synthesize imidates in a 58-96% yield from aldehydes. Thus a phase collaborative effect is observed. In the ammoxidation process, the redox cycle of MnIV/MnIII is involved and the lattice oxygen in the α-MnO2 phase acts as an active oxygen species. The O-H in methanol is activated and dissociated on the basic sites of NaxMnO2 to the adsorbed methoxyl species to facilitate the Pinner synthesis. This approach bypasses the conventional synthesis of imidates, which suffer from harsh reaction conditions and the requirement for multiple steps.

Access to nitriles from aldehydes mediated by an oxoammonium salt

A scalable, high yielding, rapid route to access an array of nitriles from aldehydes mediated by an oxoammonium salt (4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) and hexamethyldisilazane (HMDS) as an ammonia surrogate has been developed. The reaction likely involves two distinct chemical transformations: reversible silyl-imine formation between HMDS and an aldehyde, followed by oxidation mediated by the oxoammonium salt and desilylation to furnish a nitrile. The spent oxidant can be easily recovered and used to regenerate the oxoammonium salt oxidant.