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

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

Uses

Used in Pharmaceutical Industry:
5-BROMO-2-BENZYLAMINOPYRIDINE is used as a synthetic building block for the creation of various biologically active molecules and drugs. Its unique structure allows it to be a key component in the development of new pharmaceutical products.
Used in Antifungal and Antibacterial Applications:
5-BROMO-2-BENZYLAMINOPYRIDINE is used as an active ingredient in antifungal and antibacterial formulations due to its demonstrated properties against these microorganisms, which makes it a valuable asset in the development of new treatments for infections.
Used in Academic Research:
In the realm of academic research, 5-BROMO-2-BENZYLAMINOPYRIDINE is utilized for studying chemical reactions and biological processes. Its reactivity and structural features make it an interesting subject for scientific inquiry, contributing to the advancement of knowledge in chemistry and biology.
Safety Considerations:
5-BROMO-2-BENZYLAMINOPYRIDINE is typically handled and used in laboratory settings by trained professionals who adhere to strict safety guidelines. Its potential hazards and reactivity necessitate careful handling to ensure the safety of both the users and the environment.

Upstream product

• 624-28-2 2,5-dibromopyridine 
• 100-46-9 benzylamine 
• 100-39-0 benzyl bromide 
• 157020-26-3 pyridinium N-<2'-(5'-bromopyridyl)>aminide 
• 6935-27-9 N-benzylpyridin-2-amine 
• 766-11-0 5-bromo-2-fluoropyridine 
• 53939-30-3 5-bromo-2-chloropyridine 
• 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 

Relevant articles and documents

Copper-catalyzed direct amination of benzylic hydrocarbons and inactive aliphatic alkanes with arylamines

A new synthetic method toward direct C-N bond formation through saturated C-H amination of benzylic hydrocarbons and inactive aliphatic alkanes with primary aromatic amines under an inexpensive catalyst/oxidant (Cu/DTBP) system has been developed. Both aminopyridines and anilines could react smoothly with primary and secondary benzylic C-H substrates or cyclohexane to form the corresponding aromatic secondary amines in moderate to good yields. This protocol has the advantages of wide functional group tolerance and use of readily available raw materials.

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.).

Base-mediated cascade amidination/: N -alkylation of amines by alcohols

A base-mediated cascade amidination/N-alkylation reaction of amines by alcohols has been developed. For the first time, nitriles have been identified as an efficient and benign water acceptor reagent in N-alkylation. Notably, the procedure tolerates a series of functional groups, such as methoxyl, halo, vinyl and hetero groups, providing a convenient method to construct different substituted diamino compounds, 15N labeled amine and could be scaled up to 1 mol scale offering 138.7 g of the desired product in good yield in one-pot. Mechanistic studies provided strong evidence for the amidination of amines with nitriles facilitated by t-BuOK.

Inverting Conventional Chemoselectivity in Pd-Catalyzed Amine Arylations with Multiply Halogenated Pyridines

A new catalyst system capable of selective chloride functionalization in the Pd-catalyzed amination of 3,2- and 5,2- Br/Cl-pyridines is reported. A reaction optimization strategy employing ligand parametrization led to the identification of 1,1′-bis[bis(dimethylamino)phosphino]ferrocene "DMAPF", a readily available yet previously unutilized diphosphine, as a uniquely effective ligand for this transformation.

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.

Boronic species as promising inhibitors of the Staphylococcus aureus NorA efflux pump: Study of 6-substituted pyridine-3-boronic acid derivatives

In response to the extensive use of antibiotics, bacteria have evolved numerous mechanisms of defense against antimicrobial agents. Among them, extrusion of the antimicrobial agents outside the bacterial cell through efflux pumps is a major cause of concern. At first limited to one or few structurally-related antibiotics, bacterial resistance have then progressed towards cross-resistance between different classes of antibiotics, leading to multidrug-resistant microorganisms. Emergence of these pathogens requires development of novel therapeutic strategies and inhibition of efflux pumps appears to be a promising strategy that could restore the potency of existing antibiotics. NorA is the most studied chromosomal efflux pump of Staphylococcus aureus; it is known to be implied in resistance of Methicillin-resistant S. aureus (MRSA) strains against a wide range of unrelated substrates, including hydrophilic fluoroquinolones. Starting from 6-benzyloxypyridine-3-boronic acid I that we previously identified as a potential inhibitor of the NorA efflux pump against the NorA-overexpressing S. aureus 1199B strain (SA1199B), we describe here the synthesis and biological evaluation of a series of 6-(aryl)alkoxypyridine-3-boronic acids. 6-(3-Phenylpropoxy)pyridine-3-boronic acid 3i and 6-(4-phenylbutoxy)pyridine-3-boronic acid 3j were found to potentiate ciprofloxacin activity by a 4-fold increase compared to the parent compound I. In addition, it has been shown that both compounds promote Ethidium Bromide (EtBr) accumulation in SA1199B, thus corroborating their potential mode of action as NorA inhibitors.

A mild method for the regioselective bromination of 2-aminopyridines

An efficient and regioselective bromination of 2-aminopyridines was developed. The environmental friendly bromination occurs under mild and clean conditions using readily available 1-butylpyridinium bromide as the bromine source and hydrogen peroxide as the green oxidant.

Amination of halopyridines on KF-alumina under microwave irradiation

A convenient and clean synthesis of halopyridine-2-amines has been provided by amination of halopyridines on KF-alumina under microwave irradiation with good yields.

Substituted N-(2-aminophenyl)-benzamides, (E)-N-(2-aminophenyl)-acrylamides and their analogues: Novel classes of histone deacetylase inhibitors

Inhibition of histone deacetylases (HDACs) is emerging as a new strategy in human cancer therapy. Novel 2-aminophenyl benzamides and acrylamides, that can inhibit human HDAC enzymes and induce hyperacetylation of histones in human cancer cells, have been