280116-83-8

Basic information

• Product Name: 5-BROMO-2-BENZYLAMINOPYRIDINE
• Synonyms: 5-BROMO-2-BENZYLAMINOPYRIDINE;UKRORGSYN-BB BBR-050424;2-Benzylamino-5-bromopyridine;benzyl(5-bromopyridin-2- yl)amine;2-Pyridinamine,5-bromo-N-(phenylmethyl)-;5-Bromo-N-(phenylmethyl)-2-pyridinamine
• CAS NO: 280116-83-8
• Molecular Formula: C₁₂H₁₁BrN₂
• Molecular Weight: 263.14
• Mol File: 280116-83-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 124-125 °C
• Boiling Point: 355.3±32.0 °C(Predicted)
• Appearance: /
• Density: 1.470±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 4.88±0.10(Predicted)
• CAS DataBase Reference: 5-BROMO-2-BENZYLAMINOPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-2-BENZYLAMINOPYRIDINE(280116-83-8)
• EPA Substance Registry System: 5-BROMO-2-BENZYLAMINOPYRIDINE(280116-83-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 280116-83-8(Hazardous Substances Data)

Usage

General Description

5-Bromo-2-benzylaminopyridine is a chemical compound with the molecular formula C12H11BrN2. It is an organic compound that belongs to the class of aminopyridine derivatives. 5-BROMO-2-BENZYLAMINOPYRIDINE is commonly used in the pharmaceutical industry as a building block for the synthesis of various biologically active molecules and drugs. It has been shown to exhibit antifungal and antibacterial properties, making it potentially useful for the development of new pharmaceutical products. Additionally, it is also used in academic research for the study of chemical reactions and biological processes. 5-BROMO-2-BENZYLAMINOPYRIDINE is typically handled and used in laboratory settings by trained professionals following strict safety guidelines due to its potential hazards and reactivity.

Upstream product

• 624-28-2 2,5-dibromopyridine 
• 100-46-9 benzylamine 
• 6935-27-9 N-benzylpyridin-2-amine 
• 766-11-0 5-bromo-2-fluoropyridine 
• 1072-97-5 5-bromo-2-pyridylamine 
• 100-51-6 benzyl alcohol 
• 108-88-3 toluene 
• 1606181-76-3 N-(5-bromopyridin-2-yl)benzimidamide 
• 53939-30-3 5-bromo-2-chloropyridine 
• 100-39-0 benzyl bromide 
• 157020-26-3 pyridinium N-<2'-(5'-bromopyridyl)>aminide 

Relevant articles and documents

Base-Mediated Amination of Alcohols Using Amidines

Novel and efficient base-mediated N-alkylation and amidation of amidines with alcohols have been developed, which can be carried out in one-pot reaction conditions, which allows for the synthesis of a wide range of N-alkyl amines and free amides in good to excellent yields with high atom economy. In contrast to borrowing hydrogen/hydrogen autotransfer or oxidative-type N-alkylation reactions, in which alcohols are activated by transition-metal-catalyzed or oxidative aerobic dehydrogenation, the use of amidines provides an effective surrogate of amines. This circumvents the inherent necessity in N-alkylation of an oxidant or a catalyst to be stabilized by ligands.

Zinc-Catalyzed N-Alkylation of Aromatic Amines with Alcohols: A Ligand-Free Approach

An efficient zinc-catalyzed N-alkylation reaction of aromatic amines was achieved using aliphatic, aromatic, and heteroaromatic alcohols as the alkylating reagent. A variety of aniline derivatives, including heteroaromatic amines, underwent the N-alkylation reaction and furnished the corresponding monoalkylated products in good to excellent yields. The application of the reaction is also further demonstrated by the synthesis of a 2-phenylquinoline derivative from acetophenone and 2-aminobenzyl alcohol. Deuterium labeling experiments show that the reaction proceeds via a borrowing hydrogen process. (Figure presented.).

An Efficient and Selective Nickel-Catalyzed Direct N-Alkylation of Anilines with Alcohols

Herein, we developed an efficient and selective nickel-catalyzed monoalkylation of various primary alcohols with aryl and heteroaryl amines together with diols and amino alcohol derivatives. Notably, the catalytic protocol consisting of an earth-abundant and non-precious NiBr2/L1 system enables the transformations in the presence of hydroxyl, alkene, nitrile, and nitro functionalities. As a highlight, we have demonstrated the alkylation of diamine, intramolecular cyclization to N-heterocycles, and functionalization of complex vitamin E, an (±)-α-tocopherol derivative. Preliminary mechanistic studies revealed the participation of a benzylic C-H bond in the rate-determining step.