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Usage

Uses

Used in Pharmaceutical Industry:
Potassium (2-(benzyloxy)ethyl)trifluoroborate is used as a reagent in Suzuki-Miyaura cross-coupling reactions for the formation of carbon-carbon bonds. This is crucial in the synthesis of various pharmaceuticals, where the creation of specific molecular structures is essential for the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, Potassium (2-(benzyloxy)ethyl)trifluoroborate is utilized as a reagent in cross-coupling reactions to synthesize complex organic molecules. These molecules are vital for the development of agrochemicals such as pesticides and herbicides, which are designed to protect crops and enhance agricultural productivity.
Used in Materials Science:
Potassium (2-(benzyloxy)ethyl)trifluoroborate is employed in the synthesis of advanced materials through cross-coupling reactions. The formation of carbon-carbon bonds is essential in creating new materials with unique properties, such as high strength, flexibility, or conductivity, which can be applied in various industries, including electronics, automotive, and aerospace.
Used in Organic Chemistry Research:
As a versatile reagent, Potassium (2-(benzyloxy)ethyl)trifluoroborate is used in organic chemistry research to explore new synthetic pathways and develop innovative methods for the formation of carbon-carbon bonds. Its improved solubility and stability make it an attractive choice for researchers working on complex organic molecules and their potential applications.

Upstream product

• 1279123-63-5 potassium hydrogenfluoride 
• 137297-51-9 2-(2-(benzyloxy)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1462-37-9 bromoethyl-2-benzyl ether 

Downstream Products

• 1258760-02-9 1-(2-(benzyloxy)ethyl)-4-methoxybenzene 
• 666844-68-4 2-(2-(benzyloxy)ethyl)benzonitrile 
• 1408140-99-7 1-(2-(benzyloxy)ethyl)-2-methoxybenzene 
• 1408141-01-4 1-(2-(benzyloxy)ethyl)-3-methoxybenzene 
• 1408141-05-8 4-(2-(benzyloxy)ethyl)-N,N-dimethylaniline 
• 1408141-09-2 2-(2-(benzyloxy)ethyl)-1,3-dimethylbenzene 
• 1408141-12-7 1-(2-(benzyloxy)ethyl)-2-methylbenzene 
• 1408141-13-8 1-(2-(benzyloxy)ethyl)naphthalene 
• 147582-85-2 1-(2-(benzyloxy)ethyl)naphthalene 
• 1408141-17-2 1-(2-(benzyloxy)ethyl)-2-(trifluoromethyl)benzene 
• 1408141-21-8 1-(2-(benzyloxy)ethyl)-4-(trifluoromethyl)benzene 
• 1408141-25-2 1-(2-(benzyloxy)ethyl)-4-fluorobenzene 
• 119367-96-3 2-<2-(Benzyloxy)ethyl>benzonitrile 
• 1408141-36-5 1-(4-(2-(benzyloxy)ethyl)phenyl)ethanone 

Relevant academic research and scientific papers

Development of a gram-scale synthesis of pbrm, an irreversible inhibitor of 17beta-hydroxysteroid dehydrogenase type 1

Efforts toward the development of a reliable gram scale synthesis of PBRM, a potent and selective steroidal covalent inhibitor of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1), are described. Among the three synthetic routes (C-E) developed herein, route E is the most efficient one with only 6 chemical steps from commercially available estrone, and an overall yield of 13% leading to PBRM with a high HPLC grade purity (99.7%) after recrystallization. Important improvements have been achieved in this sequence from previous reported routes (A and B). Notably, we used a palladium catalyzed Suzuki-Miyaura cross-coupling reaction to rapidly install the requested C3 chain on estrone. Also, catalytic hydrogenation of the C16-enone was shortened by half using Pearlman's catalyst. Finally, we used a selective bromination through deoxygenation of alcohol at the last step of the sequence to provide PBRM without dehydration of its carboxamide functionality, a persistent problem observed in other routes. Crystals of PBRM were also obtained from recrystallization in acetonitrile and submitted to x-ray analysis, which confirmed the PBRM structure. This work now makes it possible to start a proof-of-principle in a non-human primate model for the treatment of endometriosis, while supporting its future pharmacological development.

Suzuki-Miyaura cross-coupling of potassium alkoxyethyltrifluoroborates: Access to aryl/heteroarylethyloxy motifs

The introduction of an alkoxyethyl moiety onto aromatic substructures has remained a long-standing challenge for synthetic organic chemists. The main reasons are the inherent instability of alkoxyethylmetallic species and the lack of general procedures to access them. A new method utilizing a cross-coupling strategy based on the exceptional properties of organotrifluoroborates has been developed, and the method allows an easy and efficient installation of this unit on a broad range of aryl and heteroaryl bromides.