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

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

Uses

Used in Pharmaceutical Industry:
2-Fluoro-3-pyridylboronic acid is used as a synthetic intermediate for the development of biologically active molecules. It plays a crucial role in the synthesis of various compounds with potential therapeutic applications.
Used in Heterocyclization with α-Oxocarboxylic Acids:
2-Fluoro-3-pyridylboronic acid is used as a reactant in heterocyclization reactions with α-oxocarboxylic acids. This process allows for the formation of new heterocyclic compounds with potential applications in various fields.
Used in Suzuki-Miyaura Coupling Reactions:
2-Fluoro-3-pyridylboronic acid is also utilized in Suzuki-Miyaura coupling reactions, which are widely employed in the synthesis of complex organic molecules, including pharmaceuticals and agrochemicals.
Used as a Precursor to Heteroaryl Benzylureas:
2-Fluoro-3-pyridylboronic acid serves as a precursor to heteroaryl benzylureas, which possess glycogen synthase kinase 3 inhibitory activity. These compounds have potential applications in the treatment of various diseases and disorders.
Used as a Precursor to Carboxyindoles:
It is also used as a precursor to carboxyindoles, which exhibit HCV NS5B polymerase inhibitory activity. These compounds can be employed in the development of antiviral drugs targeting Hepatitis C virus.
Used as a Precursor to Pyrazolyland Thienyl-Aminohydantoins:
2-Fluoro-3-pyridylboronic acid is utilized as a precursor to pyrazolyland thienyl-aminohydantoins, which have BACE1 inhibitory activity. These compounds are of interest in the development of drugs for the treatment of Alzheimer's disease and other neurodegenerative disorders.

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

• 1227177-64-1 4-(2-fluoropyridin-3-yl)cyclohex-3-enol 
• 1227068-28-1 (1H-benzo[d]imidazol-2-yl)(4-(3-(2-fluoropyridin-3-yl)pyrazin-2-yloxy)phenyl)methanone 
• 1220330-05-1 di-tert-butyl [(4aR,6R,8aS)-8a-[2-fluoro-5-(2-fluoropyridin-3-yl)phenyl]-6-methoxymethyl-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazine-2-yl]imidodicarbonate 
• 1220326-55-5 (4aR,6R,8aS)-8a-[2-fluoro-5-(2-fluoropyridin-3-yl)phenyl]-6-benzyloxymethyl-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-ylamine 
• 1220326-44-2 (4aR,6R,8aS)-8a-[2-fluoro-5-(2-fluoropyridin-3-yl)phenyl]-6-fluoromethyl-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-ylamine 
• 1215868-94-2 (S)-7-(2-fluoropyridin-3-yl)-3-((3-methyloxetan-3-yl)ethynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-2'-amine 
• 1187537-81-0 C₂₂H₂₀FN₃O₄S 
• 1178886-78-6 1,1-dimethylethyl N-[4-(2-fluoropyridin-3-yl)thiazol-2-yl]-N-phenylcarbamate 
• 1180016-84-5 (RS)-4-[3-(2-fluoro-pyridin-3-yl)-phenyl]-4-phenyl-4,5-dihydro-oxazol-2-ylamine 
• 1180017-17-7 (RS)-4-[3-(2-fluoro-pyridin-3-yl)-phenyl]-4-(4-methoxy-phenyl)-4,5-dihydro-oxazol-2-yl-amine formate 
• 1138033-45-0 tert-butyl {[4-(2-fluoropyridin-3-yl)-3-methyl-5-(phenylsulfonyl)-2-thienyl]methyl}methylcarbamate 
• 1138033-37-0 tert-Butyl ({5-[(3-fluorophenyl)sulfonyl]-4-(2-fluoropyridin-3-yl)-2-thienyl}methyl)methylcarbamate 
• 1138033-29-0 tert-butyl {[4-(2-fluoropyridin-3-yl)-5-(phenylsulfonyl)-2-thienyl]methyl}methylcarbamate 
• 1138419-67-6 6-(2-fluoro-3-pyridinyl)-2-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-1,2,4-triazine-3,5(2H,4H)-dione 

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.

Copper-Catalyzed Monoorganylation of Trialkyl Borates with Functionalized Organozinc Pivalates

Organozinc pivalates, a recently developed air- and moisture-stable organozinc species, were found for the first time as excellent organometallic species in the monoorganylation of trialkyl borates whereby boronic acids were prepared in high yields. The significant advantage of organozinc pivalates over another previously employed organometallic reagents, e. g., organolithium reagents, Grignard reagents and organozinc halides, is that the generation of multiorganylation byproducts such as borinic acids and trialkylboranes were completely suppressed. Additionally, the in situ generated boronates could be directly arranged into Suzuki-Miyaura type cross-coupling reactions to produce biaryls in high yields.

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.

Synthesis of novel halopyridinylboronic acids and esters. Part 2: 2,4, or 5-Halopyridin-3-yl-boronic acids and esters

This paper describes a general method for the synthesis and the isolation of novel 2,4, or 5-halopyridin-3-yl-boronic acids and esters 4, 7, 10, 13, 15. These compounds are prepared taking into account a regioselective halogen-metal exchange using nBuLi or a regioselective ortho-lithiation using lithium diisopropylamide and subsequent quenching with triisopropylborate starting from appropriate mono or dihalopyridines. All substrates studied to date provided a single regioisomeric boronic acid or ester product. Additionally, these compounds have been found to undergo Pb-catalyzed coupling with a range of arylhalides and authorize a strategy to produce new pyridines libraries.