22881-33-0

Basic information

• Product Name: (4-CHLORO-BENZYL)-PYRIDIN-2-YL-AMINE DIHYDROCHLORIDE
• Synonyms: (4-CHLORO-BENZYL)-PYRIDIN-2-YL-AMINE DIHYDROCHLORIDE;N-[(4-chlorophenyl)methyl]pyridin-2-amine;N-[(4-Chlorophenyl)methyl]-2-pyridinamine;2-[(p-chlorobenzyl)aMino]-pyridine;2-Pyridinamine,N-[(4-chlorophenyl)methyl]-
• CAS NO: 22881-33-0
• Molecular Formula: C₁₂H₁₁ClN₂
• Molecular Weight: 218.68214
• EINECS: 245-283-3
• Mol File: 22881-33-0.mol
• Article Data: 33

Chemical Properties

• Melting Point: 96-98.5 °C(Solv: benzene (71-43-2); hexane (110-54-3))
• Boiling Point: 351.7°Cat760mmHg
• Flash Point: 166.5°C
• Appearance: /
• Density: 1.251g/cm³
• Vapor Pressure: 4.04E-05mmHg at 25°C
• Refractive Index: 1.644
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 6.14±0.10(Predicted)
• CAS DataBase Reference: (4-CHLORO-BENZYL)-PYRIDIN-2-YL-AMINE DIHYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (4-CHLORO-BENZYL)-PYRIDIN-2-YL-AMINE DIHYDROCHLORIDE(22881-33-0)
• EPA Substance Registry System: (4-CHLORO-BENZYL)-PYRIDIN-2-YL-AMINE DIHYDROCHLORIDE(22881-33-0)

Safety Data

• Hazardous Substances Data: 22881-33-0(Hazardous Substances Data)

Usage

Uses

2-[(p-chlorobenzyl)amino]-pyridine is a useful synthetic intermediate. It can be prepared via selective iridium-catalyzed alkylation of (hetero)aromatic amines.

InChI:InChI=1/C12H11ClN2/c13-11-6-4-10(5-7-11)9-15-12-3-1-2-8-14-12/h1-8H,9H2,(H,14,15)

Upstream product

• 504-29-0 2-aminopyridine 
• 104-88-1 4-chlorobenzaldehyde 
• 873-76-7 para-Chlorobenzyl alcohol 
• 109-09-1 2-chloropyridine 
• 104-86-9 4-chlorobenzylamine 
• 15009-91-3 2-nitropyridine 
• 622-95-7 4-chlorobenzyl bromide 
• 59045-98-6 N-(4-chlorobenzylidene)pyridin-2-amine 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 462-08-8 pyridin-3-ylamine 
• 1445435-47-1 C₁₇H₁₉ClN₂O₂ 
• 38427-94-0 N-(tert-butoxycarbonyl)-2-aminopyridine 
• 59045-98-6 2-<(p-chlorobenzylidene)amino>pyridine 

Downstream Products

• 59-32-5 chloropyramine 
• 1263050-20-9 QKE₂₃ 

Relevant articles and documents

Isoxazole-containing pyridopyrimidinone compound as well as preparation method and application thereof

The invention relates to an isoxazole-containing pyridinopyrimidinone compound as well as a preparation method and application thereof. The compound disclosed by the invention has a structure shown as a formula (I), has excellent insecticidal activity on sogatella furcifera, brown planthopper and the like, and can be used for medicines or agents for preventing and treating hemiptera pests such as rice planthoppers and aphids. The structure and the preparation process are simple, and the production cost is low.

Effect of the ancillary ligand in N-heterocyclic carbene iridium(III) catalyzed N-alkylation of amines with alcohols

A series of air-stable N-heterocyclic carbene (NHC) Ir(III) complexes (Ir1-6), bearing various combinations of chlorine, pyridine and NHC ligands, were assayed for the N-alkylation of amines with alcohols. It was found that Ir3, with two monodentate 1,3-bis-methyl-imidazolylidene (IMe) ligands, emerged as the most active complex. A large variety of amines and primary alcohols were efficiently converted into mono-N-alkylated amines in 53–96% yields. As a special highlight, for the challenging MeOH, selective N-monomethylation could be achieved using KOH as a base under an air atmosphere. Moreover, this catalytic system was successfully applied to the gram-scale synthesis of some valuable compounds.

Ruthenium(ii) complexes with N-heterocyclic carbene-phosphine ligands for theN-alkylation of amines with alcohols

Metal hydride complexes are key intermediates forN-alkylation of amines with alcohols by the borrowing hydrogen/hydrogen autotransfer (BH/HA) strategy. Reactivity tuning of metal hydride complexes could adjust the dehydrogenation of alcohols and the hydrogenation of imines. Herein we report ruthenium(ii) complexes with hetero-bidentate N-heterocyclic carbene (NHC)-phosphine ligands, which realize smart pathway selection in theN-alkylated reactionviareactivity tuning of [Ru-H] species by hetero-bidentate ligands. In particular, complex6cbwith a phenyl wingtip group and BArF?counter anion, is shown to be one of the most efficient pre-catalysts for this transformation (temperature is as low as 70 °C, neat conditions and catalyst loading is as low as 0.25 mol%). A large variety of (hetero)aromatic amines and primary alcohols were efficiently converted into mono-N-alkylated amines in good to excellent isolated yields. Notably, aliphatic amines, challenging methanol and diamines could also be transformed into the desired products. Detailed control experiments and density functional theory (DFT) calculations provide insights to understand the mechanism and the smart pathway selectionvia[Ru-H] species in this process.