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
• Article Data: 21

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

Description

alpha-(4-chlorophenyl)pyridine-2-methanol, also known as α-(4-chlorophenyl)-2-pyridinemethanol, is an organic compound that serves as a crucial intermediate in the pharmaceutical industry. It is characterized by its light-brown solid appearance and plays a significant role in the synthesis of various medications.

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 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 98-98-6 2-Picolinic acid 
• 104-88-1 4-chlorobenzaldehyde 
• 4350-41-8 2-(4-chlorobenzyl)pyridine 
• 6318-51-0 2-(4-chlorobenzoyl)pyridine 
• 106-39-8 bromochlorobenzene 
• 1018349-32-0 2-[(4-chlorophenyl)methoxy]-pyridine 
• 110-86-1 pyridine 
• 108-90-7 chlorobenzene 
• 100-70-9 2-Cyanopyridine 
• 109-04-6 2-bromo-pyridine 
• 67-68-5 dimethyl sulfoxide 
• 79462-49-0 2-pyridyltriphenylphosphonium bromide 

Downstream Products

• 142404-69-1 2-[chloro(4-chlorophenyl)methyl]pyridine 
• 6318-51-0 2-(4-chlorobenzoyl)pyridine 
• 100542-64-1 2-[1-(4-chlorophenyl)propenyl]pyridine 
• 861902-66-1 2-[1-(4-chlorophenyl)but-1-enyl]pyridine 
• 861902-67-2 2-[1-(4-chlorophenyl)-3-methylbut-1-enyl]pyridine 
• 861902-64-9 1-(4-chlorophenyl)-1-(2-pyridyl)-1-butanol 
• 861902-65-0 1-(4-chlorophenyl)-3-methyl-1-(pyridin-2-yl)-1-butanol 
• 928046-40-6 2-[1-(4-chlorophenyl)-1-pentenyl]pyridine 
• 928046-43-9 2-[1-(4-chlorophenyl)-3,3-dimethyl-1-butenyl]pyridine 
• 928046-42-8 2-[1-(4-chlorophenyl)-4-methyl-1-pentenyl]pyridine 
• 928046-46-2 2-[1-(4-chlorophenyl)-2-phenylvinyl]pyridine 
• 928046-18-8 1-(4-chlorophenyl)-1-(2-pyridyl)-1-pentanol 
• 928046-41-7 2-[1-(4-chlorophenyl)-1-hexenyl]pyridine 
• 928046-49-5 2-[1-(4-chlorophenyl)-2-ethyl-1-butenyl]pyridine 

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.

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.