6575-27-5

Usage

Uses

Used in Pharmaceutical Industry:
2,6-Dichlorobenzylamine is used as a key intermediate in the synthesis of G protein-coupled receptor kinase 2 (GRK2) inhibitors. These inhibitors are highly selective and potent, playing a crucial role in the development of novel therapeutic agents for the treatment of various diseases, including cardiovascular disorders and neurological conditions.
Used in Agrochemical Industry:
Although not explicitly mentioned in the provided materials, 2,6-Dichlorobenzylamine, due to its chemical structure and reactivity, can also be utilized as an intermediate in the development of agrochemicals, such as herbicides, insecticides, and fungicides. Its potential applications in this industry could be attributed to its ability to form various derivatives with bioactive properties, contributing to enhanced crop protection and yield.

InChI:InChI=1/C7H7Cl2N/c8-6-2-1-3-7(9)5(6)4-10/h1-3H,4,10H2/p+1

Upstream product

• 100-97-0 hexamethylenetetramine 
• 20443-98-5 2,6-Dichlorobenzyl bromide 
• 25185-95-9 2,6-dichlorobenzaldoxime 
• 118-69-4 2,6-dichlorotoluene 
• 105219-30-5 N-Methoxy-2,6-dichlorobenzylimine 
• 1194-65-6 2,6-dichloro-benzonitrile 
• 83-38-5 2,6-dichlorobenzaldehyde 

Downstream Products

• 14885-07-5 IPRO-2 
• 102651-08-1 N-(tert-butyloxycarbonyl)-L-glutamic acid α-benzyl ester γ-(2,6-dichlorobenzylamide) 
• 23660-95-9 N⁶-(2,6-dichloro-benzyl)-adenosine 
• 64204-46-2 2-(2,6-dichlorobenzyl)isoindoline-1,3-dione 
• 1194-65-6 2,6-dichloro-benzonitrile 
• 588729-41-3 (R)-3-((2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-carbonyl)-5,5-dimethyl-thiazolidine-4-carboxylic acid 2,6-dichloro-benzylamide 
• 1017252-86-6 N-(2,6-dichlorobenzyl)-4-chloro-5-nitropyrimidin-2-amine 
• 1017252-84-4 N-(2,6-dichlorobenzyl)-2-chloro-5-nitropyrimidin-4-amine 
• 1017252-94-6 N-(2,6-Dichlorobenzyl)-6-chloro-3-nitropyridin-2-amine 
• 102651-17-2 L-glutamic acid α-benzyl ester γ-(2,6-dichlorobenzylamide) p-toluenesulfonate salt 
• 115179-53-8 5'-(2,6-dichlorobenzylamino)-2',5'-dideoxy-5-ethyluridine 
• 1196994-27-0 C₁₁H₉Cl₃N₄ 
• 1207281-02-4 6-(4-chlorophenyl)-4-[(2,6-dichlorobenzyl)amino]-5,6-dihydro-2H-1,3-oxazin-2-one 

Relevant academic research and scientific papers

Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups

The binary hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], synthesized from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce tertiary amides rapidly to the corresponding amines at 25 °C in an efficient manner. Furthermore, nitriles are converted into the corresponding amines in essentially quantitative yields. These reactions occur under ambient conditions and are completed in an hour or less. The reduction products are isolated through a simple acid-base extraction and without the use of column chromatography. Further investigation showed that (iBu)2AlBH4 has the potential to be a selective hydride donor as shown through a series of competitive reactions. Similarities and differences between (iBu)2AlBH4, DIBAL, and BMS are discussed.

PROCESS FOR PREPARATION OF HALOGENATED BENZYLAMINE AND INTERMEDIATES THEROF

The present invention provides an improved process for the preparation of halogenated benzylamine having the formula I from halogenated benzonitriles, Formula I wherein, X1 is selected from group consisting of hydrogen, chloro or fluoro, provided atleast one X1 is chloro or fluoro.

Ultra-small cobalt nanoparticles from molecularly-defined Co-salen complexes for catalytic synthesis of amines

We report the synthesis of in situ generated cobalt nanoparticles from molecularly defined complexes as efficient and selective catalysts for reductive amination reactions. In the presence of ammonia and hydrogen, cobalt-salen complexes such as cobalt(ii)-N,N′-bis(salicylidene)-1,2-phenylenediamine produce ultra-small (2-4 nm) cobalt-nanoparticles embedded in a carbon-nitrogen framework. The resulting materials constitute stable, reusable and magnetically separable catalysts, which enable the synthesis of linear and branched benzylic, heterocyclic and aliphatic primary amines from carbonyl compounds and ammonia. The isolated nanoparticles also represent excellent catalysts for the synthesis of primary, secondary as well as tertiary amines including biologically relevant N-methyl amines.

Nano-Fe3O4@SiO2-SO3H: A magnetic, reusable solid-acid catalyst for solvent-free reduction of oximes to amines with the NaBH3CN/ZrCl4 system

In this study, the immobilization of sulfonic acid on silica-layered magnetite was carried out by the reaction of ClSO3H with silica-layered magnetite. The prepared magnetic nanoparticles of Fe3O4@SiO2-SO3H were then characterized using scanning electron microscopy, energy dispersive X-ray spectroscopy, X-ray diffraction, Fourier transform infrared spectroscopy, vibrating sample magnetometry, and transmission electron microscopy. The sulfonated nanocomposite exhibited excellent catalytic activity and reusability in the reduction of various aldoximes and ketoximes with NaBH3CN in the presence of ZrCl4. All reactions were carried out under solvent-free conditions (r.t. or 75–80°C) within 3–70 min to afford amines in high to excellent yields.

The efficient solvent-free reduction of oximes to amines with NaBH3CN catalyzed by ZrCl4/nano Fe3O4 system

Reduction of various aldoximes and ketoximes to the corresponding amines was carried out easily and efficiently with NaBH3CN in the presence of ZrCl4/nano Fe3O4 system. The reactions were carried out under solvent-free conditions at room temperature or 75-80°C to afford amines in high to excellent yields.

Fe3O4-SiO2-P4VP pH-sensitive microgel for immobilization of nickel nanoparticles: An efficient heterogeneous catalyst for nitrile reduction in water

Fe3O4 magnetic nanoparticles (MNPs) were modified with (3-aminopropyl)triethoxysilane through silanization. An atom transfer radical polymerization-initiating site immobilized onto amine-functionalized Fe3O4 MNPs. The surface-initiated atom transfer radical polymerization of 4-vinylpyridine was then performed in the presence of Fe 3O4-SiO2-Br nanoparticles, which led to the formation of Fe3O4-SiO2-P4VP [P4VP=poly(4-vinylpyridine)] hybrid microgels cross-linked with Fe 3O4 MNPs. Our approach uses polymer microgels as templates for the synthesis of nickel nanoparticles (NiNPs). The tunable properties of synthesized NiNPs@Fe3O4-SiO2-P4VP pH-sensitive microgels were used in the catalytic reduction of aliphatic and aromatic nitriles. Moreover, the catalytic activity of metal nanocomposites that can be modulated by the volume transition of microgel structures with changing pH has been evaluated. TEM, X-ray photoelectron spectroscopy, thermogravimetric analysis, atomic absorption spectroscopy, XRD, UV/Vis spectroscopy, and FTIR spectroscopy were used to characterize the resultant catalyst. Mystery solved: Our approach uses polymer microgels as templates for the synthesis of nickel nanoparticles. The tunable properties of synthesized NiNPs@Fe3O 4-SiO2-P4VP [NiNPs=nickel nanoparticles; P4VP=poly(4-vinylpyridine)] pH-sensitive microgels are used in the catalytic reduction of aliphatic and aromatic nitriles. Moreover, the catalytic activity of metal nanocomposites that can be modulated by the volume transition of microgel structures with changing pH has been evaluated. Copyright

Reductions of aliphatic and aromatic nitriles to primary amines with diisopropylaminoborane

Diisopropylaminoborane [BH2Nf)Pr)2] in the presence of a catalytic amount of lithium borohydride (LiBH4) reduces a large variety of aliphatic and aromatic nitriles in excellent yields. BH 2NOPr)2 can be prepared by two methods: first by reacting diisopropylamineborane [(iPr)2N)BH3] with 1.1 equiv of n-butylhthium (n-BuLi) followed by methyl iodide (MeI), or reacting iPrN:BH 3 with 1 equiv of n-BuLi followed by trimethylsilyl chloride (TMSCl). BH2N(ZPr)2 prepared with MeI was found to reduce benzonitriles to the corresponding benzylamines at ambient temperatures, whereas diisopropylaminoborane prepared with TMSCl does not reduce nitriles unless a catalytic amount of a lithium ion source, such as LiBH4 or lithium tetraphenylborate (LiBPh4), is added to the reaction. The reductions of benzonitriles with one or more electron-withdrawing groups on the aromatic ring generally occur much faster with higher yields. For example, 2,4-dichlorobenzonitrile was successfully reduced to 2,4-dichlorobenzylamine in 99% yield after 5 h at 25 °C. On the other hand, benzonitriles containing electron-donating groups on the aromatic ring require refluxing in tetrahydrofuran (THF) for complete reduction. For instance, 4- methoxybenzonitrile was successfully reduced to 4-methoxybenzylamine in 80% yield. Aliphatic nitriles can also be reduced by the BH2N(iPr) 2/cat. LiBH4 reducing system. Benzyl cyanide was reduced to phenethylamine in 83% yield. BH2NOPr)2 can also reduce nitriles in the presence of unconjugated alkenes and alkynes such as the reduction of 2-hexynenitrile to hex-5-yn-l-amine in 80% yield. Unfortunately, selective reduction of a nitrile in the presence of an aldehyde is not possible as aldehydes are reduced along with the nitrile. However, selective reduction of the nitrile group at 25 °C in the presence of an ester is possible as long as the nitrile group is activated by an electron-withdrawing substituent. It should be pointed out that lithium aminoborohydrides (LABs) do not reduce nitriles under ambient conditions and behave as bases with aliphatic nitriles as well as nitriles containing acidic a-protons. Consequently, both LABs and BH2NOPr)2 are complementary to each other and offer methods for the selective reductions of multifunctional compounds.

1-substituted-2-mercapto benzimidazole compounds and intermediates

1-substituted-2-mercapto(or aminomethyl)benzimidazole compounds of the formula STR1 inhibit dopamine-β-hydroxylase activity. Intermediates are also disclosed.

Dopamine-β-hydroxylase inhibitors and use thereof

The compounds of this invention are 1-phenylalkyl-2-mercaptotetrazole compounds which are dopamine-β-hydroxylase inhibitors.

Benzylamines: Synthesis and evaluation of antimycobacterial properties

The synthesis of benzylamines with various N-alkyl chains and substituents in the aromatic system as well as their evaluation on Mycobacterium tuberculosis H 37 Ra are described. The most active compounds in this test, N-methyl-3-chlorobenzylamine (MIC 10.2 μg/mL), N-methyl-3,5-dichlorobenzylamine (93, MIC 10.2 μg/mL), and N-butyl-3,5-difluorobenzylamine (MIC 6.4 μg/mL), also exhibited a marked inhibitory effect on Mycobacterium marinum and Mycobacterium lufu used for the determination of antileprotic properties. The combination of 93 with aminosalicylic acid, streptomycin, or dapsone exert marked supra-additive effects on M. tuberculosis H 37 Ra.