444120-91-6

Basic information

• Product Name: 2-Chloropyridine-5-boronic acid
• Synonyms: 2-CHLORO-5-PYRIDYL BORONIC ACID;2-CHLORO-5-PYRIDINEBORONIC ACID;2-CHLOROPYRIDIN-5-YLBORONIC ACID;2-CHLOROPYRIDINE-5-BORONIC ACID;(6-CHLOROPYRIDIN-3-YL)BORONIC ACID;6-CHLOROPYRIDIN-3-YL-3-BORONIC ACID;6-CHLOROPYRIDINE-3-BORONIC ACID;6-CHLORO-3-PYRIDINYLBORONIC ACID
• CAS NO: 444120-91-6
• Molecular Formula: C₅H₅BClNO₂
• Molecular Weight: 157.36
• EINECS: -0
• Product Categories: BORONICACID;blocks;BoronicAcids;Pyridines;Pyridine;Boronic Acids & Esters;Boronic acids;Boronic acid;Organoborons;B (Classes of Boron Compounds);Chloropyridines;Halopyridines;Boronic Acids & Esters;Boric acid series;pyridine series;Boronate Ester;Potassium Trifluoroborate
• Mol File: 444120-91-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 165 °C(lit.)
• Boiling Point: 336.9 °C at 760 mmHg
• Flash Point: 157.5 °C
• Appearance: /
• Density: 1.41 g/cm³
• Vapor Pressure: 4.27E-05mmHg at 25°C
• Refractive Index: 1.559
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 6.70±0.10(Predicted)
• BRN: 9119810
• CAS DataBase Reference: 2-Chloropyridine-5-boronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloropyridine-5-boronic acid(444120-91-6)
• EPA Substance Registry System: 2-Chloropyridine-5-boronic acid(444120-91-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-22
• Safety Statements: 26-36/37-36/37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 444120-91-6(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white solid

Uses

6-Chloro-3-pyridinylboronic acid can be used:To prepare biologically significant 3-arylcoumarins by reacting with 3-chlorocoumarin through Suzuki reaction.As a substrate in the synthesis of 11-(pyridinylphenyl)steroid with progesterone agonist/antagonist profile.As a substrate in the preparation of α- secondary and tertiary pyridines by the reaction of pyridotriazoles with boronic acids.As a substrate in the palladium-catalyzed α-arylation of saturated cyclic amines and N-methyl amines.

InChI:InChI=1/C5H5BClNO2/c7-5-2-1-4(3-8-5)6(9)10/h1-3,9-10H

Upstream product

• 16110-09-1 2,5 dichloropyridine 
• 53939-30-3 5-bromo-2-chloropyridine 
• 69045-79-0 2-choro-5-iodopyridine 
• 1072-97-5 5-bromo-2-pyridylamine 
• 504-29-0 2-aminopyridine 
• 20511-12-0 2-amino-5-iodopyridine 

Downstream Products

• 101001-97-2 6-chloro-3,3'-bipyridine 
• 41288-96-4 6-chloropyridine-3-ol 
• 66600-05-3 2-chloro-5-phenylpyridine 
• 1213233-33-0 N-{3-[3-(6-chloro-pyridin-3-yl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-3-trifluoromethyl-benzamide 
• 1018833-41-4 3-(4-aminophenyl)-6-chloropyridine 
• 942206-24-8 6,6''-dichloro-3,2':4',3''-terpyridine 
• 1208222-41-6 V⁽⁶⁵¹⁾U₀₃₁₈ 
• 1224952-64-0 C₂₀H₁₃ClN₂O₂ 
• 1235099-38-3 potassium (6-chloropyridin-3-yl)trifluoroborate 
• 1254565-63-3 propane-1-sulfonic acid {3-[5-(6-chloro-pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-2,4-difluoro-phenyl}-amide 
• 1222850-43-2 2-(1-{[3-(6-chloropyridin-3-yl)phenyl]methyl}-1H-indole-3-sulfonyl)-N-(5-methyl-1,2-oxazol-3-yl)acetamide 
• 1352212-46-4 tert-butyl (2S)-2-{5-[4-(6-{2-[(2S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl]-1H-benzimidazol-5-yl}pyridin-3-yl)phenyl]-1H-imidazol-2-yl}pyrrolidine-1-carboxylate 
• 1352212-13-5 methyl {(2S)-1-[(2S)-2-{5-[5-(4-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-imidazol-5-yl}phenyl)pyridin-2-yl]-1H-benzimidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate 

Relevant articles and documents

METHOD FOR PRODUCING 6-HALOGENO-3-ARYLPYRIDINE DERIVATIVE

[Problem] The present invention provides an industrially advantageous production method of a 6-halogeno-3-arylpyridine derivative in which cryogenic condition is not required, production step is short, and an isomer difficult to be separated is not produced as a by-product. [Solution] A production method of a 6-halogeno-3-arylpyridine derivative represented by the general formula (III) comprising: the first step reacting a 2, 5-dihalogenopyridine derivative represented by the general formula (I) with a magnesiation reagent; and the second step reacting the product obtained from the above-described first step, in the presence of a palladium compound, with a halogenoaryl derivative represented by the general formula (II).

5-Substituted, 6-substituted, and unsubstituted 3-heteroaromatic pyridine analogues of nicotine as selective inhibitors of cytochrome P-450 2A6

A series of 5- and 6-substituted and unsubstituted 3-heteroaromatic analogues of nicotine were synthesized in an effort to delineate the structural requirements for selectively inhibiting human cytochrome P-450 (CYP) 2A6, the major nicotine metabolizing enzyme. Thiophene, substituted thiophene, furan, substituted furan, imidazole, substituted imidazole, pyridine, substituted pyridine, thiazole, and quinoline moieties were used to replace the N-methylpyrrolidine ring of nicotine. Bromo and methyl groups were introduced at the 5-position of the pyridine ring and fluoro, chloro, and methoxy groups were placed at the 6-position of the pyridine ring in order to explore the structure-activity relationship (SAR) of inhibition of CYP2A6. The inhibitory activity of the most potent CYP2A6 inhibitors on the functional activity of human cytochrome P450s 3A4, 2E1, 2B6, 2C9, 2C19, and 2D6 was also examined to determine inhibitor selectivity. We identified 36 compounds that were more potent than nicotine at inhibition of coumarin 7-hydroxylase (CYP2A6) activity. We also found a number of compounds to be highly selective for the inhibition of human CYP2A6 versus the other human CYPs examined.

An efficient route to 6-(het)aryl-2-methyl-2,3-dihydro-1H-pyridin-4-ones as potential nAChRs ligands

A new efficient pathway to synthesise 6-(het)aryl-2-methyl-2,3-dihydro-1H- pyridin-4-ones is described. This reaction sequence involved, as a key step, a Suzuki cross-coupling reaction between various boronic acids and an 6-iodo-2,3-dihydropyridin-4-one. A final deprotecting step furnished the attempted products.