166328-14-9

Basic information

• Product Name: Potassium 2-furantrifluoroborate
• Synonyms: Potassium 2-furantrifluoroborate;CHEMMAKER CMBC-00037;POTASSIUM FURAN-2-YLTRIFLUOROBORATE;Potassium 2-furantrifluoroborate 96%;potassium:trifluoro(furan-2-yl)boranuide
• CAS NO: 166328-14-9
• Molecular Formula: C₄H₃BF₃O*K
• Molecular Weight: 173.97
• Product Categories: Boronic Acids and Derivatives;Heteroaryl;Trifluoroborate Salts;Molander Ates;Organoborons
• Mol File: 166328-14-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 293-303 °C
• Appearance: /
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: Potassium 2-furantrifluoroborate(CAS DataBase Reference)
• NIST Chemistry Reference: Potassium 2-furantrifluoroborate(166328-14-9)
• EPA Substance Registry System: Potassium 2-furantrifluoroborate(166328-14-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 166328-14-9(Hazardous Substances Data)

Usage

Uses

An organotrifluoroborate involved in:Ether-forming cross-coupling reactionsOxidation using OxoneCross-coupling with alkyl electrophiles and halopurinesSuzuki-Miyaura reactionsOrganotrifluoroborates as versatile and stable boronic acid surrogates

Upstream product

• 13331-23-2 fur-2-ylboronic acid 
• 7789-23-3 potassium fluoride 
• 1279123-63-5 potassium hydrogenfluoride 

Downstream Products

• 55484-03-2 2-(2'-furyl)pyridine 
• 27110-82-3 2-(furan-2-yl)pyrimidine 
• 1101167-53-6 1-(4-(furan-2-yl)phenyl)-1H-pyrrole 
• 17113-31-4 2-(4-methoxyphenyl)furan 
• 38527-54-7 2-(2'-methylphenyl)furan 
• 64468-77-5 2-(4-cyanophenyl)furan 
• 53355-25-2 methyl 4-(2-furanyl)benzoate 
• 69836-64-2 N-(4-furan-2-ylphenyl)acetamide 
• 1101167-52-5 3-(furan-2-yl)-4,5-dimethoxybenzonitrile 
• 60456-77-1 4-furylbenzaldehyde 
• 35216-08-1 2-(4-acetylphenyl)furan 
• 28123-72-0 2-(4-nitrophenyl)furan 
• 1172994-77-2 9-benzyl-8-(furan-2-yl)adenine 
• 13331-23-2 fur-2-ylboronic acid 

Relevant articles and documents

Refining boron-iodane exchange to access versatile arylation reagents

Aryl(Mes)iodonium salts, which are multifaceted aryl transfer reagents, are synthesized via boron-iodane exchange. Modification to both the nucleophilic (aryl boron) and electrophilic (mesityl-λ3-iodane) reaction components results in improved yield and faster reaction time compared to previous conditions. Mechanistic studies reveal a pathway that is more like transmetallation than SEAr.

Arylketones as Aryl Donors in Palladium-Catalyzed Suzuki-Miyaura Couplings

Herein, we report the arylation, alkylation, and alkenylation of aryl ketones via a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction. The use of the pyridine-oxazoline ligand is the key to the cleavage of the unstrained C-C bond. The late-stage arylation of aryl ketones derived from drugs and natural products demonstrated the synthetic utility of this protocol.

Design and synthesis of furyl/thineyl pyrroloquinolones based on natural alkaloid perlolyrine, lead to the discovery of potent and selective PDE5 inhibitors

Based on perlolyrine (1), a natural alkaloid with weak PDE5 potency from the traditional Chinese aphrodisiac plant Tribulus terrestris L., a series α-substituted tetrahydro-β-carboline (THβC) derivatives were synthesized via T+BF4--mediated oxidative C–H functionalization of N-aryl THβCs with diverse potassium trifluoroborates. Following Winterfeldt oxidation afforded the corresponding furyl/thienyl pyrroloquinolones, of which 5-ethylthiophene/ethylfuran derivatives 20a–b were identified as the most potent and selective PDE5 inhibitors. Among the enantiomers, (S)-20a and (S)-20b (IC50 = 0.52 and 0.39 nM) were found to be more effective than their (R)-antipode, display favorable pharmacokinetic profiles, exert in vitro vasorelaxant effects on the isolated thoracic aorta, and exhibit in vivo efficacy in the anesthetized rabbit erectile model.