42365-43-5

Usage

Uses

Used in Pharmaceutical Industry:
4-Chlorobenzylamine hydrochloride is used as a synthetic building block for the creation of various pharmaceuticals, leveraging its reactivity to form essential chemical bonds in drug molecules.
Used in Agrochemical Industry:
In the agrochemical sector, 4-Chlorobenzylamine hydrochloride serves as a key component in the synthesis of agrochemicals, contributing to the development of effective products for agricultural applications.
Used in Dye Industry:
4-Chlorobenzylamine hydrochloride is utilized as a precursor in the production of dyes, capitalizing on its chemical properties to create a spectrum of colorants for various industries.
Used in Organic Chemistry Research:
4-Chlorobenzylamine hydrochloride is employed as a reagent in organic chemistry reactions such as reductive amination and nucleophilic substitution, facilitating important research and development processes.
Used in Material Science:
It has been studied for its potential use in developing novel materials and biomolecules, indicating its broad applicability in advancing material science and related fields.
However, due to its potential to cause irritation to the skin, eyes, and respiratory system, it is crucial to handle 4-Chlorobenzylamine hydrochloride with appropriate safety measures to prevent contact or inhalation.

InChI:InChI=1/C7H8ClN.ClH/c8-7-3-1-6(5-9)2-4-7;/h1-4H,5,9H2;1H

Upstream product

• 92550-15-7 N,N'-bis(4-chlorobenzyl)urea 
• 51172-60-2 ethyl (4-chlorobenzyl)carbamate 
• 623-03-0 4-Cyanochlorobenzene 
• 15118-53-3 2,2-dimethyl-4-oxohexanoic acid 
• 103252-87-5 1-[(4-chlorophenyl)methyl]-1-(phenyl)hydrazine hydrochloride 
• 619-56-7 4-chlorobenzamide 
• 27032-10-6 4-chlorobenzyl azide 
• 14062-24-9 4-chloro-benzeneacetic acid, ethyl ester 
• 104-86-9 4-chlorobenzylamine 
• 20101-92-2 2-(4-chlorophenyl)acetamide 
• 1849-02-1 2-chloro-1-methyl-benzimidazole 
• 29559-24-8 4-chlorophenylnitromethane 
• 65334-65-8 methanol diethyl ether 
• 57676-51-4 2-(4-chlorophenyl)acetic hydrazide 

Downstream Products

• 65608-74-4 N-(4-chlorobenzyl)urea 
• 93070-54-3 C₉H₉ClN₄ 
• 128043-68-5 [3-(4-Chloro-benzyl)-2,4,5-trioxo-imidazolidin-1-yl]-acetic acid ethyl ester 
• 40408-50-2 (4-chloro-benzyl)-imidazolidinetrione 
• 104375-81-7 N-nitroso-N-(p-chlorobenzyl)urea 
• 220364-27-2 1-(4-Chlorobenzyl)-5-hydroxymethyl-1H-imidazole 
• 1206635-29-1 (R)-N-4-(chloro)benzyl 2-(tert-butoxycarbonyl)amino-3-hydroxypropionamide 
• 1616493-27-6 ethyl 3-[(4-chlorobenzyl)amino]-2-[(2,6-dichloropyridin-3-yl)carbonyl]acrylate 
• 1616493-10-7 ethyl 7-[4-(1,3-benzothiazol-2-yl)piperazin-1-yl]-1-(4-chlorobenzyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate 
• 1616493-20-9 7-[4-(1,3-benzothiazol-2-yl)piperazin-1-yl]-1-(4-chlorobenzyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid 
• 1616493-39-0 ethyl 7-chloro-1-(4-chlorobenzyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate 
• 58010-69-8 N-(4-chlorobenzoyl)benzamide 

Relevant academic research and scientific papers

Base-Catalyzed Hydrosilylation of Nitriles to Amines and Esters to Alcohols

Base-catalyzed hydrosilylation of nitriles to amines and esters to silylated alcohols is reported. This protocol tolerates electron-rich and electron-neutral olefins and works in the presence of basic functional groups (e. g. tertiary amines) but fails for acidic substrates, such as phenols and NH anilines. This catalytic system does not tolerate carbonyl groups, such as aldehydes, ketones, esters and carbamides, which are reduced to corresponding alcohols and amines. With the exact amount of silane, esters can be selectively reduced in the presence of nitriles, but the selectivity drops for the pairs ester/carboxamide and carboxamide/nitrile. Through competition experiments, the following preference in functional group reactivity was determined: ester > carboxamide > nitrile.

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.

Green method for catalyzing reduction reaction of aliphatic nitro derivative

The invention relates to a green method for catalyzing reduction reaction of aliphatic nitro derivatives. According to the method, non-transition metal compounds, namely triethyl boron and potassium tert-butoxide, are used as a catalytic system for the first time, an aliphatic nitro derivative and pinacolborane which is low in price and easy to obtain are catalyzed to be subjected to a reduction reaction under mild conditions, and an aliphatic amine hydrochloride product is synthesized after acidification with a hydrochloric acid aqueous solution. Compared with a traditional method, the method generally has the advantages that the catalyst is cheap and easy to obtain, operation is convenient, and reaction is safe. The selective reduction reaction of the aliphatic nitro derivative catalyzed by the non-transition metal catalyst and pinacol borane is realized for the first time, and the aliphatic amine hydrochloride product is synthesized through acidification treatment of the hydrochloric acid aqueous solution, so that a practical new reaction strategy is provided for laboratory preparation or industrial production.

Reduction of Amides to Amines with Pinacolborane Catalyzed by Heterogeneous Lanthanum Catalyst La(CH2C6H4NMe2- o)3@SBA-15

Hydroboration of amides is a useful synthetic strategy to access the corresponding amines. In this contribution, it was found that the supported lanthanum benzyl material La(CH2C6H4NMe2-o)3@SBA-15 was highly active for the hydroboration of primary, secondary, and tertiary amides to amines with pinacolborane. These reactions selectively produced target amines and showed good tolerance for functional groups such as -NO2, -halogen, and -CN, as well as heteroatoms such as S and O. This reduction procedure exhibited the recyclable and reusable property of heterogeneous catalysts and was applicable to gram-scale synthesis. The reaction mechanisms were proposed based on some control experiments and the previous literature. This is the first example of hydroborative reduction of amides to amines mediated by heterogeneous catalysts.

Deoxygenation of primary amides to amines with pinacolborane catalyzed by Ca[N(SiMe3)2]2(THF)2

Deoxygenative reduction of amides is a challenging but favorable synthetic method of accessing amines. In the presence of a catalytic amount of Ca[N(SiMe3)2]2(THF)2, pinacolborane (HBpin) could efficiently reduce a broad scope of amides, primary amides in particular, into corresponding amines. Functional groups and heteroatoms showed good tolerance in this process of transformation, and a plausible reaction mechanism was proposed.

Hydrosilylative reduction of primary amides to primary amines catalyzed by a terminal [Ni-OH] complex

A terminal [Ni-OH] complex1, supported by triflamide-functionalized NHC ligands, catalyzes the hydrosilylative reduction of a range of primary amides into primary amines in good to excellent yields under base-free conditions with key functional group tolerance. Catalyst1is also effective for the reduction of a variety of tertiary and secondary amides. In contrast to literature reports, the reactivity of1towards amide reduction follows an inverse trend,i.e., 1° amide > 3° amide > 2° amide. The reaction does not follow a usual dehydration pathway.

Metal-Free Synthesis of Heteroaryl Amines or Their Hydrochlorides via an External-Base-Free and Solvent-Free C-N Coupling Protocol

Herein, a metal-free and solvent-free protocol was developed for the C-N coupling of heteroaryl halides and amines, which afforded numerous heteroaryl amines or their hydrochlorides without any external base. Further investigations elucidated that the basicity of amines and specific interactions derived from the X-ray crystallography analysis of 3j′·HCl played pivotal roles in the reactions. Moreover, this protocol was scalable to gram scales and applicable to drug molecules, which demonstrated its practical value for further applications.

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.

Synthesis of Molybdenum Pincer Complexes and Their Application in the Catalytic Hydrogenation of Nitriles

A series of molybdenum(0), (I) and (II) complexes ligated by different PNP and NNN pincer ligands were synthesized and structurally characterized. Along with previously described Mo?PNP complexes Mo-1 and Mo-2, all prepared compounds were tested in the catalytic hydrogenation of aromatic nitriles to primary amines. Among the applied catalysts, Mo-1 is particularly well suited for the hydrogenation of electron-rich benzonitriles. Additionally, two aliphatic nitriles were transformed into the desired products in 80 and 86 percent, respectively. Moreover, catalytic intermediate Mo-1a was isolated and its role in the catalytic cycle was subsequently demonstrated.

Silicon hydrogenation reaction method of organic boron and inorganic alkali catalysis amide (by machine translation)

The method is characterized in that organic boron and inorganic bases are used as catalysts, silane is used as a reducing agent, primary amide is reduced to primary amine or dehydration dinitrile, the secondary amide is reduced to a secondary amine or aldimine, and the tertiary amide is reduced to tertiary amine. The method has the advantages of simple operation, mild reaction conditions, wide substrate universality, good functional group compatibility and the like, and has the characteristics of good stability, cheap and accessible catalyst, simple and convenient operation, high practicality and the like. (by machine translation)