5465-63-4

Usage

Uses

Used in Organic Synthesis:
2-Bromobenzylamine hydrochloride is used as an intermediate in organic synthesis for the production of various pharmaceuticals and chemical compounds. Its ability to react with sulfonyl chloride makes it a valuable component in the synthesis of sulfonamide-based drugs, which have a wide range of applications in the medical field.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Bromobenzylamine hydrochloride is utilized as a key intermediate in the synthesis of specific medications. Its role in creating sulfonamide compounds allows for the development of drugs that can be used to treat a variety of health conditions, including bacterial infections and other diseases.
Used in Chemical Research:
2-Bromobenzylamine hydrochloride is also employed in chemical research for studying the properties and reactions of bromine-containing organic compounds. Its unique structure and reactivity make it an interesting subject for scientists to explore and understand the behavior of similar compounds in various chemical processes.

InChI:InChI=1/C7H8BrN/c8-7-4-2-1-3-6(7)5-9/h1-4H,5,9H2/p+1

Upstream product

• 854634-26-7 1-bromo-2-(nitromethyl)benzene 
• 4001-73-4 2-Bromobenzamide 
• 2042-37-7 o-cyanobromobenzene 

Downstream Products

• 138883-38-2 N-[(2-bromophenyl)methyl]benzamide 
• 215653-98-8 N-(2-Bromo-benzyl)-N-(1,1-dioxo-2,3-dihydro-1H-1λ⁶-thiophen-3-yl)-acetamide 
• 215653-97-7 Acetic acid 4-[acetyl-(2-bromo-benzyl)-amino]-1,1-dioxo-tetrahydro-1λ⁶-thiophen-3-yl ester 
• 879-74-3 N-[(2-bromophenyl)methyl]-N'-methylurea 
• 162356-90-3 N-(tert-butoxycarbonyl)-2-bromobenzylamine 
• 1291713-01-3 N-(2-bromo)benzyl picolinamide 
• 1527507-23-8 3H-benzo[c]naphtho[2,1-e]azepine 

Relevant academic research and scientific papers

Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications

Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for the retention of various reducible functionalities and the compatibility of sensitive groups toward hydroboration, thereby providing a mild, chemoselective, and facile strategy to form anilines, as well as heteroaryl and aliphatic amine derivatives, with broad scope and particularly high turnover numbers (up to 1.8 × 106). Mechanistic studies, based on theoretical calculations, indicate that the CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin; it serves as an H-shuttle to facilitate deoxygenative hydroboration. The preparation of several commercially available pharmaceuticals by means of this strategy highlights its potential application in medicinal chemistry.

Transition metal-free catalytic reduction of primary amides using an abnormal NHC based potassium complex: Integrating nucleophilicity with Lewis acidic activation

An abnormal N-heterocyclic carbene (aNHC) based potassium complex was used as a transition metal-free catalyst for reduction of primary amides to corresponding primary amines under ambient conditions. Only 2 mol% loading of the catalyst exhibits a broad substrate scope including aromatic, aliphatic and heterocyclic primary amides with excellent functional group tolerance. This method was applicable for reduction of chiral amides and utilized for the synthesis of pharmaceutically valuable precursors on a gram scale. During mechanistic investigation, several intermediates were isolated and characterized through spectroscopic techniques and one of the catalytic intermediates was characterized through single-crystal XRD. A well-defined catalyst and isolable intermediate along with several stoichiometric experiments, in situ NMR experiments and the DFT study helped us to sketch the mechanistic pathway for this reduction process unravelling the dual role of the catalyst involving nucleophilic activation by aNHC along with Lewis acidic activation by K ions.

Exhaustive Chemoselective Reduction of Nitriles by Catalytic Hydrosilylation Involving Cooperative Si-H Bond Activation

A chemoselective method for the catalytic hydrosilylation of nitriles to either the imine or amine oxidation level is reported. The chemoselectivity is controlled by the hydrosilane used. The usefulness of the nitrile-to-amine reduction is demonstrated for a diverse set of aromatic and aliphatic nitriles, and the amines are easily isolated after hydrolysis as their hydrochloride salts. This exhaustive nitrile reduction proceeds at room temperature.

A method for the production of primary amines

The invention relates to the field of chemical industry and particularly relates to a method for preparing primary amine by using the raw materials including halogenated hydrocarbon (or hydrocarbon alcohol sulfonate) and ammonia water (or formamide). The method comprises the following three steps: (1) imidization: 3,4-diarylfuran-2,5-diketone (I) reacts with ammonia (or formamide) and the like to obtain 3,4-diaryl-1H-pyrrole-2,5-diketone (II); (2) N-hydrocarbylation: 3,4-diaryl-1H-pyrrole-2,5-diketone (II) generates an N-hydrocarbylation reaction with halogenated hydrocarbon (or hydrocarbon alcohol sulfonate) in the presence of alkali to obtain N-hydrocarbyl-3,4-diaryl-1H-pyrrole-2,5-diketone (III); and (3) hydrolysis: N-hydrocarbyl-3,4-diaryl-1H-pyrrole-2,5-diketone (III) is subjected to alkali hydrolysis to obtain primary amine and the generated 2,3-diaryl maleate is subjected to acid treatment and automatic ring closing to form 3,4-diaryl furan-2,5-diketone (I) which is subjected to imidization and directly applied to the N-hydrocarbylation reaction. The method provided by the invention has the characteristics that the 3,4-diaryl furan-2,5-diketone can be circularly used at a high recovery rate, the molar ratio of the raw materials is low, and the yield of the product primary amine is high.

Straightforward access to cyclic amines by dinitriles reduction

1,1,3,3-Tetramethyldisiloxane (TMDS) and polymethylhydrosiloxane (PMHS), when associated with titanium(IV) isopropoxide, provide two convenient systems for the reduction of nitriles into the corresponding primary amines. Kinetics of the two systems have been studied by 1H NMR and demonstrated that reduction with PMHS occurs faster than with TMDS. These two titanium-based systems reduce both aromatic and aliphatic nitriles in the presence of Br, CC, NO2, OH, and cyclopropyl-ring. In the case of cyclopropyl-nitriles, the formation of secondary amines, which come from an intermolecular reductive alkylation reaction was observed. This result was exploited for the reduction of dinitriles, which led, in one-step, to azepane, piperidine, pyrrolidine, and azetidine derivatives through an intramolecular reductive alkylation reaction.

A mild and efficient method for the reduction of nitriles

A simple and useful method for the reduction of nitriles into the corresponding amines using a tetramethyldisiloxane/titanium(IV) isopropoxide reducing system is described. The synthetic approach is straightforward and provides primary amines as hydrochloride salt in almost quantitative yield. Other advantages of this method, such as easy-to-handle hydride source, inert by-products, that is, TiO2 and oligomeric siloxanes, make it very attractive to prepare primary amines.