27652-89-7

Basic information

• Product Name: alpha-(4-chlorophenyl)pyridine-2-methanol
• Synonyms: alpha-(4-chlorophenyl)pyridine-2-methanol;4-Chlorophenyl-2-pyridinylmethanol;a-(4-Chlorophenyl)-2-pyridinemethanol;NSC 31264;NSC 47970;((4-Chlorophenyl)-2-pyridinemethanol);α-(p-Chlorophenyl)-2-pyridinemethanol;alpha-(4-chlorophenyl)-2-pyridinemethanol
• CAS NO: 27652-89-7
• Molecular Formula: C₁₂H₁₀ClNO
• Molecular Weight: 219.6669
• EINECS: 248-592-1
• Product Categories: Aromatics;Heterocycles
• Mol File: 27652-89-7.mol

Chemical Properties

• Melting Point: 78-80?C
• Boiling Point: 364.3 °C at 760 mmHg
• Flash Point: 174.1 °C
• Appearance: light-brown solid
• Density: 1.275 g/cm³
• Vapor Pressure: 6.01E-06mmHg at 25°C
• Refractive Index: 1.614
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 12.46±0.20(Predicted)
• CAS DataBase Reference: alpha-(4-chlorophenyl)pyridine-2-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-(4-chlorophenyl)pyridine-2-methanol(27652-89-7)
• EPA Substance Registry System: alpha-(4-chlorophenyl)pyridine-2-methanol(27652-89-7)

Safety Data

• Hazardous Substances Data: 27652-89-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
alpha-(4-chlorophenyl)pyridine-2-methanol is used as a reagent for the synthesis of Carbinoxamine (Maleate salt: C175920), a histamine H1 antagonist. It is utilized in this application due to its ability to contribute to the development of medications that can effectively block histamine receptors, providing relief from allergy symptoms.
Additionally, alpha-(4-chlorophenyl)pyridine-2-methanol is used as an intermediate in the synthesis of Bepotastine besylate (B317000), a non-sedating H1-antagonist with anti-inflammatory activity. Its role in this process is essential for creating a medication that can alleviate allergy symptoms without causing drowsiness, making it a valuable compound in the development of antihistamine drugs.

InChI:InChI=1/C12H10ClNO/c13-10-6-4-9(5-7-10)12(15)11-3-1-2-8-14-11/h1-8,12,15H

Upstream product

• 1121-60-4 pyridine-2-carbaldehyde 
• 106-39-8 bromochlorobenzene 
• 110-86-1 pyridine 
• 4350-41-8 2-(4-chlorobenzyl)pyridine 
• 67-68-5 dimethyl sulfoxide 
• 109-04-6 2-bromo-pyridine 
• 104-88-1 4-chlorobenzaldehyde 
• 100-70-9 2-Cyanopyridine 
• 108-90-7 chlorobenzene 
• 1018349-32-0 2-[(4-chlorophenyl)methoxy]-pyridine 
• 6318-51-0 2-(4-chlorobenzoyl)pyridine 
• 98-98-6 2-Picolinic acid 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 694-59-7 pyridine N-oxide 

Downstream Products

• 142404-69-1 2-[chloro(4-chlorophenyl)methyl]pyridine 
• 486-16-8 2-[(4-chlorophenyl)-2-pyridinylmethoxy]-N,N-dimethylethanamine 

Relevant articles and documents

Synthesis of optically active α-(p-Chlorophenyl)pyridylmethanols with plant cell cultures

We have synthesized optically active α-(p- chlorophenyl)pyridylmethanols by reduction or by hydrolysis with plant cell cultures.

Green synthesis method of polyaryl substituted methanol

The invention relates to a green synthesis method of polyaryl substituted methanol, in particular to a method for efficiently synthesizing polyaryl substituted methanol in a polar aprotic solvent under the condition of an oxidizing agent by taking polyaryl substituted methane as a raw material and alkali as an additive. The method provided by the invention is green and environment-friendly, avoids using expensive metal catalysts, and has the advantages of low cost, few reaction steps, short time, high yield and the like.

From Pyridine- N-oxides to 2-Functionalized Pyridines through Pyridyl Phosphonium Salts: An Umpolung Strategy

The reactions of pyridine-N-oxides with Ph3P under the developed conditions provide an unprecedented route to (pyridine-2-yl)phosphonium salts. Upon activation with DABCO, these salts readily serve as functionalized 2-pyridyl nucleophile equivalents. This umpolung strategy allows for the selective C2 functionalization of the pyridine ring with electrophiles, avoiding the generation and use of unstable organometallic reagents. The protocol operates at ambient temperature and tolerates sensitive functional groups, enabling the synthesis of otherwise challenging compounds.

Targeting the aryl hydrocarbon receptor with a novel set of triarylmethanes

The aryl hydrocarbon receptor (AhR) is a chemical sensor upregulating the transcription of responsive genes associated with endocrine homeostasis, oxidative balance and diverse metabolic, immunological and inflammatory processes, which have raised the pharmacological interest on its modulation. Herein, a novel set of 32 unsymmetrical triarylmethane (TAM) class of structures has been synthesized, characterized and their AhR transcriptional activity evaluated using a cell-based assay. Eight of the assayed TAM compounds (14, 15, 18, 19, 21, 22, 25, 28) exhibited AhR agonism but none of them showed antagonist effects. TAMs bearing benzotrifluoride, naphthol or heteroaromatic (indole, quinoline or thiophene) rings seem to be prone to AhR activation unlike phenyl substituted or benzotriazole derivatives. A molecular docking analysis with the AhR ligand binding domain (LBD) showed similarities in the binding mode and in the interactions of the most potent TAM identified 4-(pyridin-2-yl (thiophen-2-yl)methyl)phenol (22) compared to the endogenous AhR agonist 5,11-dihydroindolo[3,2-b]carbazole-12-carbaldehyde (FICZ). Finally, in silico predictions of physicochemical and biopharmaceutical properties for the most potent agonistic compounds were performed and these exhibited acceptable druglikeness and good ADME profiles. To our knowledge, this is the first study assessing the AhR modulatory effects of unsymmetrical TAM class of compounds.

Transition-Metal Free Chemoselective Hydroxylation and Hydroxylation-Deuteration of Heterobenzylic Methylenes

We developed an approach for direct selective hydroxylation of heterobenzylic methylenes to secondary alcohols avoiding overoxidation to ketones by using a KOBu-t/DMSO/air system. Most reactions could reach completion in several minutes to give hydroxylated products in 41-76% yields. Using DMSO-d6, this protocol resulted in difunctionalization of heterobenzylic methylenes to afford α-deuterated secondary alcohols (>93% incorporation). By employing this method, active pharmaceutical ingredients carbinoxamine and doxylamine were synthesized in two steps in moderate yields.

Ligand-Free Iridium-Catalyzed Dehydrogenative ortho C?H Borylation of Benzyl-2-Pyridines at Room Temperature

A convenient and ligand-free iridium-catalyzed dehydrogenative ortho C?H borylation of benzyl-2-pyridines has been developed. The reaction proceeds smoothly at room temperature using pinacolborane as a borylating reagent in the presence of catalytic amount of [IrOMe(COD)]2. The reaction is compatible with many functional groups, providing a vast array of ortho borylated products in moderate to excellent yields with excellent selectivities. (Figure presented.).

IMPROVED PROCESS FOR THE MANUFACTURE OF BEPOTASTINE AND ITS BESILATE SALT

The present invention discloses a process for preparation of Bepotastine and its Besilate salt of formula I with good yield and purity. The invention also describes a process for recycle and reuse of the Ethyl-4-hydroxy piperidine-1-carboxylate from the aqueous medium after isolating the 2-[(S)-(4-Chlorophenyl)(piperidin-4- yloxy)methyl]pyridine, for subsequent batches in the production of Ethyl 4-[(4- Chlorophenyl)(pyridin-2-yl)methoxy]piperidine-1-carboxylate. The invention further discloses novel intermediates, viz., 2-[Chloro(4- chlorophenyl)methyl]pyridine hydrochloride and bis{2-[(S)-(4- Chlorophenyl)(piperidin-4-yloxy)methyl]pyridine} Dibenzoyl tartrate, useful in the preparation of Bepotastine and its Besilate salt.

Iridium-Catalyzed Highly Enantioselective Transfer Hydrogenation of Aryl N-Heteroaryl Ketones with N-Oxide as a Removable ortho-Substituent

A highly enantioselective transfer hydrogenation of non-ortho-substituted aryl N-heteroaryl ketones, using readily available chiral diamine-derived iridium complex (S,S)-1f as a catalyst and sodium formate as a hydrogen source in a mixture of H2O/i-PrOH (v/v = 1:1) under ambient conditions, is described. The chiral aryl N-heteroaryl methanols were obtained with up to 98.2% ee by introducing an N-oxide as a removable ortho-substituent. In contrast, no more than 15.1% ee was observed in the absence of an N-oxide moiety. Furthermore, the practical utility of this protocol was also demonstrated by gram-scale asymmetric synthesis of bepotastine besilate in 51% total yield and 99.9% ee.

Method for preparing alpha-(4-chlorphenyl)pyridine-2-methanol

The invention discloses a method for preparing alpha-(4-chlorphenyl)pyridine-2-methanol, and relates to the technical field of organic synthesizing. The method comprises the following steps of using 2-cyanopyridine as an initial raw material; generating Grignard reaction with a Grignard reagent of para chlorobromobenzene to generate alpha-(4-chlorphenyl)pyridine-2-methanol; generating reduction reaction with sodium borohydride to obtain the alpha-(4-chlorphenyl)pyridine-2-methanol. The synthesizing method has the advantages that the corrosion of raw materials to production equipment is avoided, the used solvent can be recycled and reutilized, the green chemical concept is met, the hazard of pollution to environment is decreased, and the production cost is reduced; the yield rate and purity of the alpha-(4-chlorphenyl)pyridine-2-methanol are higher, and the total molar yield rate is 70% or above.

DOPAMINE D2 RECEPTOR LIGANDS

The present invention relates to novel dopamine D2 receptor ligands. The invention further relates to functionally-biased dopamine D2 receptor ligands and the use of these compounds for treating or preventing central nervous system and systemic disorders associated with dysregulation of dopaminergic activity.