5005-37-8

Basic information

• Product Name: alpha-(4-chlorophenyl)pyridine-2-acetonitrile
• Synonyms: alpha-(4-chlorophenyl)pyridine-2-acetonitrile;P-CHLOROPHENYL-2-PYRIDYL ACETONITRILE;α-(4-Chlorophenyl)-2-pyridineacetonitrile;2-(4-chlorophenyl)-2-(2-pyridyl)acetonitrile;2-(4-chlorophenyl)-2-pyridin-2-yl-ethanenitrile;(4-Chloro-phenyl)-pyridin-2-yl-acetonitrile;2-(4-chlorophenyl)-2-(pyridin-2-yl)acetonitrile(WXC06332)
• CAS NO: 5005-37-8
• Molecular Formula: C₁₃H₉ClN₂
• Molecular Weight: 228.67696
• EINECS: 225-678-7
• Mol File: 5005-37-8.mol
• Article Data: 17

Chemical Properties

• Melting Point: 67.5-67.8 °C
• Boiling Point: 357.1ºC at 760 mmHg
• Flash Point: 169.8ºC
• Appearance: /
• Density: 1.238g/cm3
• Vapor Pressure: 2.79E-05mmHg at 25°C
• Refractive Index: 1.599
• Storage Temp.: 2-8°C
• PKA: 4.08±0.10(Predicted)
• CAS DataBase Reference: alpha-(4-chlorophenyl)pyridine-2-acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-(4-chlorophenyl)pyridine-2-acetonitrile(5005-37-8)
• EPA Substance Registry System: alpha-(4-chlorophenyl)pyridine-2-acetonitrile(5005-37-8)

Safety Data

• Hazardous Substances Data: 5005-37-8(Hazardous Substances Data)

Usage

General Description

Alpha-(4-chlorophenyl)pyridine-2-acetonitrile, also known as 4'-chloro-2-cyanopyridine, is a chemical compound with the molecular formula C12H7ClN2. It is a derivative of pyridine and contains a chlorophenyl group and a cyano group. alpha-(4-chlorophenyl)pyridine-2-acetonitrile is used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It also has potential applications in organic synthesis and material science. Alpha-(4-chlorophenyl)pyridine-2-acetonitrile should be handled with care as it is a potentially hazardous chemical and may have harmful effects if not properly used and stored.

InChI:InChI=1/C13H9ClN2/c14-11-6-4-10(5-7-11)12(9-15)13-3-1-2-8-16-13/h1-8,12H

Upstream product

• 109-09-1 2-chloropyridine 
• 140-53-4 p-chlorobenzyl cyanide 
• 109-04-6 2-bromo-pyridine 
• 106-39-8 bromochlorobenzene 
• 2739-97-1 pyridine-2-acetonitrile 

Downstream Products

• 873375-63-4 4,4-diethoxy-2-(4-chloro-phenyl)-2-[2]pyridyl-butyronitrile 
• 1198318-49-8 2-(4-bromobutyl)-4-(4-chloro-phenyl)-5,6,7,8-tetrahydropyrido[1,2-c]pyrimidine-1,3-dione 
• 1149339-65-0 C₁₈H₁₆BrClN₂O₂ 
• 20619-13-0 Didesmethylchlorpheniramine 
• 1025944-75-5 (4-Chloro-phenyl)-piperidin-2-yl-acetic acid 
• 108904-38-7 4-(4-chloro-phenyl)-pyrido[1,2-c]pyrimidine-1,3-dione 
• 6318-51-0 2-(4-chlorobenzoyl)pyridine 
• 100375-20-0 (4-chloro-phenyl)-[2]pyridyl-acetic acid amide 
• 82418-18-6 2-(4-Chlorphenyl)-3-methyl-2-(2-pyridyl)-4-(1,2,4-triazol-1-yl)-3-butennitril 
• 122376-81-2 2-(4-Chloro-phenyl)-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-pyridin-2-yl-butyronitrile 

Relevant articles and documents

Preparation method of chlorpheniramine maleate intermediate

The invention belongs to the field of organic medicine synthesis, and particularly relates to a preparation method of a chlorpheniramine maleate intermediate. The method comprises the following steps: reacting chlorobenzyl cyanide with 2-halogen pyridine under the action of sodium amide to obtain a 2-(4-chlorphenyl)-2-(pyridine-2-yl)acetonitrile crude product; The main improvement point is as follows: the 2-(4-chlorphenyl)-2-(pyridine-2-yl)acetonitrile crude product reacts with an ethyl acetate solution of hydrogen chloride to obtain 2-(4-chlorphenyl)-2-(pyridine-2-yl)acetonitrile hydrochloride precipitate. The method disclosed by the invention is simple in operation steps, is relatively low in equipment requirement, can obtain good-state hydrochloride, is easy to purify, is relatively high in product purity and is suitable for industrial scale-up production.

Synthesis of novel pyrido[1,2-c]pyrimidine derivatives with 6-fluoro-3-(4-piperidynyl)-1,2-benzisoxazole moiety as potential ssri and 5-ht1a receptor ligands

Two series of novel 4-aryl-2H-pyrido[1,2-c]pyrimidine (6a–i) and 4-aryl-5,6,7,8-tetrahydropyrido[1,2-c]pyrimidine (7a–i) derivatives were synthesized. The chemical structures of the new compounds were confirmed by1H and13C NMR spectroscopy and ESI-HRMS spectrome-try. The affinities of all compounds for the 5-HT1A receptor and serotonin transporter protein (SERT) were determined by in vitro radioligand binding assays. The test compounds demonstrated very high binding affinities for the 5-HT1A receptor of all derivatives in the series (6a–i and 7a–i) and generally low binding affinities for the SERT protein, with the exception of compounds 6a and 7g. Extended affinity tests for the receptors D2, 5-HT2A, 5-HT6 and 5-HT7 were conducted with regard to selected compounds (6a, 7g, 6d and 7i). All four compounds demonstrated very high affinities for the D2 and 5-HT2A receptors. Compounds 6a and 7g also had high affinities for 5-HT7, while 6d and 7i held moderate affinities for this receptor. Compounds 6a and 7g were also tested in vivo to identify their functional activity profiles with regard to the 5-HT1A receptor, with 6a demonstrating the activity profile of a presynaptic agonist. Metabolic stability tests were also conducted for 6a and 6d.

Structure-activity relationship and cardiac safety of 2-aryl-2-(pyridin-2-yl)acetamides as a new class of broad-spectrum anticonvulsants derived from Disopyramide

A series of 2-aryl-2-(pyridin-2-yl)acetamides were synthesized and screened for their anticonvulsant activity in animal models of epilepsy. The compounds were broadly active in the ‘classical’ maximal electroshock seizure (MES) and subcutaneous Metrazol (scMET) tests as well as in the 6 Hz and kindling models of pharmacoresistant seizures. Furthermore, the compounds showed good therapeutic indices between anticonvulsant activity and motor impairment. Structure-activity relationship (SAR) trends clearly showed the highest activity resides in unsubstituted phenyl derivatives or compounds having ortho- and meta- substituents on the phenyl ring. The 2-aryl-2-(pyridin-2-yl)acetamides were derived by redesign of the cardiotoxic sodium channel blocker Disopyramide (DISO). Our results show that the compounds preserve the capability of the parent compound to inhibit voltage gated sodium currents in patch-clamp experiments; however, in contrast to DISO, a representative compound from the series 1 displays high levels of cardiac safety in a panel of in vitro and in vivo experiments.