174669-73-9

Basic information

• Product Name: 2-Fluoro-3-pyridylboronic acid
• Synonyms: AKOS BRN-0506;2-FLUORO-3-PYRIDINEBORONIC ACID;2-FLUOROPRYRIDINE-3-BORONIC ACID;2-FLUOROPYRIDIN-3-YLBORONIC ACID;2-FLUOROPYRIDINE-3-BORONIC ACID;2-FLUOROPYRIDINE-3-BORONIC ACID HYDRATE;Boronic acid, (2-fluoro-3-pyridinyl)- (9CI);2-Fluoro-3-pyridylboronicacid
• CAS NO: 174669-73-9
• Molecular Formula: C₅H₅BFNO₂
• Molecular Weight: 140.91
• Product Categories: HALIDE;PYRIDINE;blocks;BoronicAcids;Pyridines;Boronic Acids & Esters;Fluorinated;Organoborons;Boronic acid;Boronic Acids & Esters;Boric acid series;Boronate Ester;Potassium Trifluoroborate
• Mol File: 174669-73-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 172°C
• Boiling Point: 322.6 °C at 760 mmHg
• Flash Point: 148.9 °C
• Appearance: White powder
• Density: 1.34 g/cm³
• Vapor Pressure: 0.000114mmHg at 25°C
• Refractive Index: 1.507
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: soluble in Methanol
• PKA: 6.68±0.58(Predicted)
• BRN: 9119935
• CAS DataBase Reference: 2-Fluoro-3-pyridylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluoro-3-pyridylboronic acid(174669-73-9)
• EPA Substance Registry System: 2-Fluoro-3-pyridylboronic acid(174669-73-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: No
• HazardClass: IRRITANT
• Hazardous Substances Data: 174669-73-9(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Reactant involved in:Heterocyclization eith α-oxocarboxylic acidsSuzuki-Miyaura coupling reactionsAdditionally used as a precursor to biologically active molecules including:Heteroaryl benzylureas with glycogen synthase kinase 3 inhibitory activityCarboxyindoles with HCV NS5B polymerase inhibitory activityPyrazolyl- and thienyl-aminohydantoins with BACE1 inhibitory activity

InChI:InChI=1/C5H5BFNO2/c7-5-4(6(9)10)2-1-3-8-5/h1-3,9-10H

Upstream product

• 5419-55-6 Triisopropyl borate 
• 372-48-5 2-fluoropyridine 

Downstream Products

• 654075-30-6 2-(2-fluoro-pyridin-3-yl)-cyclohex-1-enecarboxylic acid ethyl ester 
• 1187537-81-0 C₂₂H₂₀FN₃O₄S 
• 943605-97-8 6-(2-fluoropyridin-3-yl)-N-methylpyrimidin-4-amine 
• 684287-41-0 9-benzhydryloxy-7-(4-fluoro-benzyl)-5-(2-fluoro-pyridin-3-yl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one 
• 654075-32-8 2-(2-hydroxy-pyridin-3-yl)-cyclohex-1-enecarboxylic acid 

Relevant articles and documents

Synthesis of two fluoro analogues of the nicotinic acetylcholine receptor agonist UB-165

Two racemic fluoropyridine analogues 4 and 5 of the potent nicotinic agonist UB-165 have been synthesized. Halogenated pyridines 7 and 12 provided the organometallic reagents needed for the Negishi and Suzuki coupling reactions used for the preparation of 4 and 5, and the N-vinyloxycarbonyl protecting group of 8 and 15 was cleaved using a novel trifluoroacetic acid-mediated deprotection protocol. Analogue 4 retained high binding affinity at rat brain α4β2 and α7 nicotinic receptors.

Expedient Synthesis of Highly Substituted Fused Heterocoumarins

(Matrix presented) Highly substituted fused coumarins can be prepared in two steps starting from the appropriate boronic acids and enol triflates. The synthesis of fused pyrano[2,3-d]pyrimidin-7-one (1) is a key example to demonstrate the potential of the method in the elaboration of new coumarin scaffolds.