13382-54-2

Basic information

• Product Name: 2-CHLORO-6-PHENYLPYRIDINE
• Synonyms: 2-CHLORO-6-PHENYLPYRIDINE;6-Chloro-2-phenylpyridine
• CAS NO: 13382-54-2
• Molecular Formula: C₁₁H₈ClN
• Molecular Weight: 189.64
• Mol File: 13382-54-2.mol

Chemical Properties

• Melting Point: 157-159℃
• Boiling Point: 307℃
• Flash Point: 168℃
• Appearance: /
• Density: 1.186
• Vapor Pressure: 0.00137mmHg at 25°C
• Refractive Index: 1.588
• Storage Temp.: 2-8°C
• PKA: -0.17±0.10(Predicted)
• CAS DataBase Reference: 2-CHLORO-6-PHENYLPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-6-PHENYLPYRIDINE(13382-54-2)
• EPA Substance Registry System: 2-CHLORO-6-PHENYLPYRIDINE(13382-54-2)

Safety Data

• Hazardous Substances Data: 13382-54-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-6-phenylpyridine is utilized as a key building block for the synthesis of various pharmaceutical drugs. Its unique structure allows for the development of compounds with specific biological activities, contributing to the advancement of medicinal chemistry.
Used in Agrochemicals:
In the agrochemical sector, 2-chloro-6-phenylpyridine serves as a precursor for the synthesis of bioactive molecules with pesticidal properties, enhancing crop protection and contributing to sustainable agriculture.
Used in Coordination Chemistry:
2-Chloro-6-phenylpyridine has been studied for its potential as a ligand in coordination chemistry. Its ability to form stable complexes with metal ions makes it a valuable component in the design of new materials with applications in catalysis, sensing, and other areas.
Used in Cellular Pathway Research:
2-CHLORO-6-PHENYLPYRIDINE has also demonstrated biological activity in various cellular pathways, making it a useful tool in biological and medicinal research for understanding and potentially modulating these pathways for therapeutic purposes.

InChI:InChI=1/C11H8ClN/c12-11-8-4-7-10(13-11)9-5-2-1-3-6-9/h1-8H

Upstream product

• 1008-89-5 2-phenylpyridine 
• 1984-23-2 p-nitrophenyl isocyanide 
• 108-86-1 bromobenzene 
• 652148-92-0 2-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 
• 1122-58-3 dmap 
• 591-51-5 phenyllithium 
• 2402-78-0 2,6-dichloropyridine 
• 603-33-8 triphenylbismuthane 
• 98-80-6 phenylboronic acid 
• 1184955-09-6 2-(tert-butoxy)-6-phenylpyridine 
• 5140-72-7 2-bromo-6-chloro-pyridine 
• 201230-82-2 carbon monoxide 
• 591-50-4 iodobenzene 
• 263698-99-3 2-chloro-6-(tributylstannyl)pyridine 

Downstream Products

• 557111-97-4 2-chloro-6-[2-(diphenylphosphanyl)phenyl]pyridine 
• 154544-94-2 diphenyl(6-phenyl-2-pyridyl)phosphine 
• 3558-69-8 2,6-diphenylpyridine 
• 1218790-96-5 6-phenyl-(2-pyridineboronic acid) 
• 1335148-39-4 C₂₄H₁₇ClN₂O 
• 856421-73-3 2-(6'-phenylpyridin-2'-ylsulfanyl)ethanamine 
• 1095242-43-5 (1S,2R)-3-(6-chloro-pyridin-2-yl)cyclohexane-3,5-diene-1,2-diol 
• 1033125-47-1 2-hexadecyl-6-phenylpyridine 
• 1033125-46-0 2-decyl-6-phenylpyridine 

Relevant articles and documents

Direct Synthesis of Benzoylpyridines from Chloropyridines via a Palladium-Carbene Catalyzed Carbonylative Suzuki Cross-Coupling Reaction

The use of N-heterocyclic carbene-type ligands with palladium catalysts allows the activation of chloropyridines and chloroquinoline towards carbonylative cross-coupling with phenylboronic acid for the synthesis of unsymmetrical biaryl ketones.

Selective ortho C-H Activation of Pyridines Directed by Lewis Acidic Boron of PBP Pincer Iridium Complexes

Transition-metal mediated C-H functionalization has emerged as a powerful method in the chemistry relevant to the synthesis of pharmaceuticals, agrochemicals, and advanced materials. Because organic molecules typically contain multiple types of C-H bonds, selective C-H functionalization is a major ongoing challenge. C-H activation of heteroatom-containing organics has often been approached via the use of the directing effect, whereby the coordination to the basic heteroatom directs the reactive metal center to a specific C-H bond. We now report a different approach where the nitrogen donor in pyridine derivatives coordinates to an ancillary Lewis acidic boryl ligand directly attached to the metal (iridium) center, as opposed to the metal itself. This topology directs the iridium center to activate a different C-H bond than in the cases of directing donor coordination to the metal. Using this strategy, we demonstrate ortho-regiospecific C-H activation of pyridines and an example of the subsequent functionalization via C-C bond formation.

Micelle-Enabled Suzuki-Miyaura Cross-Coupling of Heteroaryl Boronate Esters

We report a micellar protocol for Suzuki-Miyaura cross-coupling of heteroaryl boronic esters with aryl or heteroaryl halides. The micellar catalysis enables this coupling reaction to run under mild conditions, which avoids the decomposition of heteroaryl boronate esters and allows for high chemoselectivity for cross-coupling reaction with 6-chloropridine-2-boronic ester. The micellar protocol expands the scope of the cross-coupling reaction with challenging heteroaryl boronic esters and complements the existing cross-coupling methods for construction of heterobiaryl building blocks.

A new aromatic amine compound and its preparation and use (by machine translation)

The invention discloses a novel aromatic amine compound, and the compound molecule of the general formula: Wherein R1 , R2 , R3 Are hydrogen atom or the carbon atom number 1 - 30 alkyl or the carbon atom number 6 - 50 car

Cross-coupling study of iodo/chloropyridines and 2-chloroquinoline with atom-economic triarylbismuth reagents under Pd-catalysis

This study describes the palladium-catalyzed couplings of iodopyridines, chloropyridines, and chloroquinoline with atom-economic BiAr3 reagents in sub-stoichiometric loadings. Mono-arylations of iodo and chloropyridines produced arylpyridines i

Synthesis and characterization of hydrophilic theophylline base compounds and their use as ligands in the microwave assisted Suzuki-Miyaura couplings of halopyridines in water Dedicated to the memory of Prof. Dr. Armando Cabrera Ortiz pioneer of Catalysis in Mexico. Great Researcher but above all a Great Human Being

Xanthine derivatives, caffeine (L1), theobromine (L2), theophylline (L3), 7-(β-hydroxyethyltheophylline) (L4), (7-(2,3-dihydroxypropyl)theophylline) (L5), and theophylline 7-acetic acid (L6) and the acetylated derivatives of the later three (L7-L9) were employed as ligands for the in situ palladium catalyzed Suzuki-Miyaura cross couplings of a series of halogenated pyridines. Optimized conditions were found where the diacetylated ligand (L8) was determined to be the best for this process, producing good to excellent yields in the couplings of halogenated anilines with phenylboronic acid under mild reaction conditions in water using microwave irradiation.

Discovery of amide replacements that improve activity and metabolic stability of a bis-amide smoothened antagonist hit

A bis-amide antagonist of Smoothened, a seven-transmembrane receptor in the Hedgehog signaling pathway, was discovered via high throughput screening. In vitro and in vivo experiments demonstrated that the bis-amide was susceptible to N-acyl transferase mediated amide scission. Several bioisosteric replacements of the labile amide that maintained in vitro potency were identified and shown to be metabolically stable in vitro and in vivo.

The AZARYPHOS family of ligands for ambifunctional catalysis: Syntheses and use in ruthenium-catalyzed anti-markovnikov hydration of terminal alkynes

The family of AZARYPHOS (aza-aryl-phosphane) phosphane ligands, containing a phosphine unit and sterically shielded nitrogen lone pairs in the ligand periphery, is introduced as a tool for developing ambifunctional catalysis by the metal center and nitrogen lone pairs in the ligand sphere. General synthetic strategies have been developed to synthesize over 25 examples of structurally diverse (6-aryl-2pyridyl)phosphanes (ARPYPHOS), (6alkyl-2-pyridyl)phosphanes (ALPY-PHOS), 4,6-disubsituted l,3-diazin-2ylphosphanes or l,3,5-triazin-2- ylphosphanes, quinazolinylphosphanes, quinolinylphosphanes, and others. The scalable syntheses proceed in a few steps. The incorporation of AZARYPHOS ligands (L) into complexes [RuCp(L)2(MeCN)][PF6] (Cp = cyclopentadieny1)gives catalysts for the anti-Markovnikov hydration of terminal alkynes of the highest known activities. Electronic and steric ligand effects modulate the reaction kinetics over a range of two orders of magnitude. These results highlight the importance of using structurally diverse ligand families in the process of developing cooperative ambifunctional catalysis by a metal and its ligand.

Practical routes to 2,6-disubstituted pyridine derivatives

We report the synthesis of a series of 2,6-disubstituted pyridines in a straightforward manner starting from readily available 2-substituted pyridines. The main sequence involves a selective ?-lithiation reaction with halogen functionalization followed by

Palladium-N-heterocyclic carbene an efficient catalytic system for the carbonylative cross-coupling of pyridine halides with boronic acids

Carbonylative cross-coupling of different pyridyl halides with various boronic acids was studied using catalytic systems constituted of N-heterocyclic carbene type ligands and palladium. These systems easily obtained in situ from the corresponding imidazolium salt and palladium acetate appear more efficient toward bromopyridines than catalysts based on hindered and basic alkylphosphines such as tricyclohexylphosphine. Their higher efficiency was also evidenced by coupling using chloro- or dichloropyridines and chloroquinolines, which practically do not react with catalytic systems based on phosphines.