1042512-03-7

Basic information

• Product Name: N-benzyl-3-chloropyridin-2-amine
• Synonyms: N-benzyl-3-chloropyridin-2-amine;2-PYRIDINAMINE,3-CHLORO-N-(PHENYLMETHYL)-
• CAS NO: 1042512-03-7
• Molecular Formula: C₁₂H₁₁ClN₂
• Molecular Weight: 218.68214
• Mol File: 1042512-03-7.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-benzyl-3-chloropyridin-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyl-3-chloropyridin-2-amine(1042512-03-7)
• EPA Substance Registry System: N-benzyl-3-chloropyridin-2-amine(1042512-03-7)

Safety Data

• Hazardous Substances Data: 1042512-03-7(Hazardous Substances Data)

Upstream product

• 2402-77-9 2,3-dichloro-pyridine 
• 100-46-9 benzylamine 
• 96424-68-9 2-bromo-3-chloropyridine 
• 1480-64-4 3-chloro-2-fluoropyridine 

Downstream Products

• 1294517-65-9 N-benzyl-3-phenylpyridine-2-amine 
• 1370412-45-5 N-benzhydryl-3-phenylpyridin-2-amine 
• 1370412-46-6 3-phenyl-N-(phenyl(p-tolyl)methyl)pyridin-2-amine 
• 1370412-47-7 N-((4-(tert-butyl)phenyl)(phenyl)methyl)-3-phenylpyridin-2-amine 
• 1370412-48-8 N-((4-fluorophenyl)(phenyl)methyl)-3-phenylpyridin-2-amine 
• 1416556-09-6 N-{[4-chlorophenyl](phenyl)methyl}-3-phenylpyridin-2-amine 
• 1416556-11-0 3-phenyl-N-{phenyl[4-(trifluoromethyl)phenyl]methyl}-pyridin-2-amine 

Relevant articles and documents

Quaternary Ammonium Salts as Alkylating Reagents in C-H Activation Chemistry

A rhodium(I)-catalyzed alkylation reaction of benzylic amines via C(sp3)-H activation using quaternary ammonium salts as alkyl source is described. The reaction proceeds via in situ formation of an olefin via Hofmann elimination, which is the actual alkylating reagent. This represents an operationally simple method for substituting gaseous and liquid olefins with solid quaternary ammonium salts as alkylating reagents, which is transferable to other C-H activation protocols as well.

A convenient palladium-catalyzed azaindole synthesis

A one-pot protocol is described which allows direct access to azaindoles from amino-halopyridines and ketones.

Mechanistic investigations and substrate scope evaluation of ruthenium-catalyzed direct sp3 arylation of benzylic positions directed by 3-substituted pyridines

A highly efficient direct arylation process of benzylic amines with arylboronates was developed that employs Ru catalysis. The arylation takes place with greatest efficiency at the benzylic sp3 carbon. If the distance to the activating aryl ring is increased, arylation is still possible but the yield drops significantly. Efficiency of the CH activation was found to be significantly increased by use of 3-substituted pyridines as directing groups, which can be removed after the transformation in high yield. Calculation of the energy profile of different rotamers of the substrate revealed that presence of a substituent in the 3-position favors a conformation with the CH2 group adopting a position in closer proximity to the directing group and facilitating C-H insertion. This operationally simple reaction can be carried out in argon atmosphere as well as in air and under neutral reaction conditions, displaying a remarkable functional group tolerance. Mechanistic studies were carried out and critically compared to mechanistic reports of related transformations.