4152-09-4

Usage

Uses

Used in Chemical Synthesis:
N-Benzylethylenediamine is used as a chemical intermediate for the synthesis of various compounds, such as N-benzyl-N,N′,N′-tris(tert-butyloxycarbonylmethyl)ethylenediamine and 3-benzyl-2-(phenyl-2-sulfonate)-2-imidazoline tetraheptylammonium salt. Its role in these syntheses is crucial for the development of new chemical entities with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-Benzylethylenediamine may be utilized in the development of novel drug candidates due to its ability to participate in the synthesis of complex organic molecules. Its involvement in the formation of N,N,N′-trisubstituted guanidines can lead to the creation of new compounds with potential therapeutic properties.
Used in Research and Development:
N-Benzylethylenediamine is also used in research and development settings, where it can contribute to the advancement of chemical knowledge and the discovery of new materials or compounds with specific applications in various fields, such as materials science, environmental science, and biotechnology.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C9H14N2/c10-6-7-11-8-9-4-2-1-3-5-9/h1-5,11H,6-8,10H2/p+2

Upstream product

• 151-56-4 ethyleneimine 
• 100-46-9 benzylamine 
• 64-18-6 formic acid 
• 104-71-2 N,N'-bis(benzyliden)ethylendiamine 
• 141-53-7 sodium formate 
• 496039-67-9 1,2-bis-(benzenesulfonyl-benzyl-amino)-ethane 
• 4938-92-5 N-(2-formylaminoethyl)formamide 
• 100-52-7 benzaldehyde 
• 100-44-7 benzyl chloride 
• 107-15-3 ethylenediamine 
• 6274-53-9 N-(2-(phenylsulfonamido)ethyl)acetamide 
• 620-05-3 iodomethylbenzene 
• 936-49-2 2-phenyl-2-imidazoline 
• 100-51-6 benzyl alcohol 

Downstream Products

• 107235-83-6 N-Benzyl-N,N'-dibenzoylethylenediamine 
• 114599-41-6 N-benzyl-N',N'''-diphenyl-N,N''-ethanediyl-bis-thiourea 
• 6096-36-2 1-benzyl-2-methyl-4,5-dihydro-1H-imidazole 
• 67696-35-9 (3-benzyl-2-diethylamino-[1,3,2]diazaphospholidin-1-yl)-phosphonous acid bis-diethylamide 
• 67696-34-8 (3-benzyl-2-dimethylamino-[1,3,2]diazaphospholidin-1-yl)-phosphonous acid bis-dimethylamide 
• 72702-56-8 2--1-phenylethanol 
• 131203-44-6 2-[(2-Benzylamino-ethyl)-(2-hydroxy-2-phenyl-ethyl)-amino]-1-phenyl-ethanol 
• 97832-16-1 N-Benzyl-N'-benzoylethylenediamine Hydrochloride 
• 61764-86-1 1-benzyl-4,5-dihydroimidazole 
• 107235-80-3 N-Benzyl-N'-cyclohexylcarbonylethylenediamine 
• 167566-34-9 1-benzyl-3-(trifluoromethyl)piperazine 

Relevant academic research and scientific papers

Low emission epoxy resin composition

An epoxy resin composition, the curing components of which contain at least one amine of formula (I) and optionally at least one amine A which is, in particular, an adduct of a polyamine and an epoxide. The amine for formula (I) is used in particular in the form of a reaction product of the reductive alkylation of 1,2-ethylenediamine and an aldehyde or ketone. The epoxy resin composition is used in particular as a low-emission, room-temperature-curing epoxy-resin coating. It is characterised by good processibility, quick curing, high hardness, a nice surface and a low tendency to yellowing.

Design, Synthesis, and Synergistic Activity of Eight-Membered Oxabridge Neonicotinoid Analogues

Insecticide synergists are sought-after due to their potential in improving the pesticide control efficacy with a reduced dose of an active ingredient. We previously reported that a cis-configuration neonicotinoid (IPPA08) exhibited specific synergistic activity toward neonicotinoid insecticides. In this study, we synthesized a series of structural analogues of IPPA08 by converting the pyridyl moiety of IPPA08 into phenyl groups, via facile double-Mannich condensation reactions between nitromethylene compounds and glutaraldehyde. All of the oxabridged neonicotinoid compounds were found to increase the toxicity of imidacloprid against Aphis craccivora. Notably, compound 25 at 0.75 mg/L lowered the LC50 value of imidacloprid against A. craccivora by 6.54-fold, while a 3.50-fold reduction of the LC50 value was observed for IPPA08. The results of bee toxicity test showed that compound 25 display selectivity in its effects on imidacloprid toxicity against the honey bee (Apis mellifera L.). In summary, replacing the pyridyl ring with a phenyl ring was a viable approach to obtain a novel synergist with oxabridged moiety for neonicotinoid insecticides.

A new kind of acetylcholine esterase inhibitors and its preparation method and application (by machine translation)

The present invention provides a novel acetyl choline esterase inhibitor and its preparation method and application, in particular, the invention discloses a formula A shown with double AChE binding site of substituted acridine compound, and its preparation method and as acetylcholinesterase inhibitors. The preparation of the novel compounds of this invention demonstrate good inhibit acetylcholine esterase role, can be used as a preparation for treating and preventing HAMER (AD) application value. (by machine translation)

Design, synthesis and antimycobacterial activity of novel imidazo[1,2-a]pyridine-3-carboxamide derivatives

We report herein the design and synthesis of “novel imidazo [1,2-a]pyridine-3-carboxamides (IPAs)” bearing a variety of different linkers, based on the structure of IMB-1402 discovered in our lab. Results reveal that 2,6-dimethyl-N-[2-(phenylamino)ethyl] IPAs with an electron-donating group on the benzene ring as a potent scaffold. Compounds 26g and 26h have considerable activity (MIC: 0.041–2.64 μM) against drug-sensitive/resistant MTB strains, and they have acceptable safety indices against MTB H37Rv with the SI values of 4395 and 1405, respectively. Moreover, N-[2-(piperazin-1-yl)ethyl] moiety was also identified as a potentially alternative linker (compound 31), opening a new direction for further SAR studies.

Highly enantioselective synthesis of 2,3-dihydro-1 H-imidazo[2,1-a isoindol-5(9b H)-ones via catalytic asymmetric intramolecular cascade imidization-nucleophilic addition-lactamization

Highly enantioselective catalytic asymmetric intramolecular cascade imidization-nucleophilic addition-lactamization of N1-alkylethane-1,2-diamine with methyl 2-formylbenzoate catalyzed by a chiral phosphoric acid represents the first efficient method for the preparation of medicinally interesting chiral 2,3-dihydro-1H-imidazo[2,1-a]isoindol-5(9bH)-ones with high yields and excellent enantioselectivities. This strategy has been shown to be quite general toward various methyl 2-formylbenzoates.

Structure-activity relationships of novel substituted naphthalene diimides as anticancer agents

Novel 1,4,5,8-naphthalenetetracarboxylic diimide (NDI) derivatives were synthesized and evaluated for their antiproliferative activity on a wide number of different tumor cell lines. The prototypes of the present series were derivatives 1 and 2 characterized by interesting biological profiles as anticancer agents. The present investigation expands on the study of structure-activity relationships of prototypes 1 and 2, namely, the influence of the different substituents of the phenyl rings on the biological activity. Derivatives 3-22, characterized by a different substituent on the aromatic rings and/or a different chain length varying from two to three carbon units, were synthesized and evaluated for their cytostatic and cytotoxic activities. The most interesting compound was 20, characterized by a linker of three methylene units and a 2,3,4-trimethoxy substituent on the two aromatic rings. It displayed antiproliferative activity in the submicromolar range, especially against some different cell lines, the ability to inhibit Taq polymerase and telomerase, to trigger caspase activation by a possible oxidative mechanism, to downregulate ERK 2 protein and to inhibit ERKs phosphorylation, without acting directly on microtubules and tubuline. Its theoretical recognition against duplex and quadruplex DNA structures have been compared to experimental thermodynamic measurements and by molecular modeling investigation leading to putative binding modes. Taken together these findings contribute to define this compound as potential Multitarget-Directed Ligands interacting simultaneously with different biological targets.

Synthesis and selected properties of N-substituted pyrrolo[2,1-c]-1,3- diazacycloalkano[1,2-a]pyrazinones

The reactions of methyl α-(2-formyl-1H-pyrrol-1-yl)carboxylates with N-substituted aliphatic 1,2-, 1,3-, and 1,4-diamines afford new pyrrole-containing heterocyclic systems: 1,2,3,10b-tetrahydroimidazo[1,2-a] pyrrolo[2,1-c]pyrazin-5(6H)-ones, 1,3,4,11b-tetrahydro-2H-pyrrolo[2′, 1′:3,4]pyrazino[1,2-a]pyrimidin-6(7H)-ones, and 1,2,3,4,5,12b-hexahydro- pyrrolo[2′,1′:3,4]pyrazino[1,2-a][1,3]diazepin-7(8H)-ones. The reduction of these compounds with different reagents was studied.

Design, synthesis, and bioactivity of cyanonitrovinyl neonicotinoids as potential insecticides

A series of cyanonitrovinyl neonicotinoids were designed and synthesized via five steps in about 35% overall yields. All compounds were structurally characterized by 1H nuclear magnetic resonance (NMR), 13C NMR, infrared (IR), and high-resolution mass spectrometry (HRMS), and single-crystal X-ray diffraction analysis of 2-[1-[(6-chloropyridin-3-yl)methyl] -2-imidazolidinylidene]-2-nitroacetonitrile revealed that the double bond is (E)-configured. The preliminary agriculture bioassay indicated that one compound exhibited moderate insecticidal activity against pea aphid. Springer-Verlag 2010.

Robust and electron-rich cis-palladium(II) complexes with phosphine and carbene ligands as catalytic precursors in Suzuki coupling reactions

A new imidazolinium ligand precursor [L2H]Cl (2) was prepared in 86 % yield. Compared with its imidazolium counterpart, [L1H]Cl (1), 2 is very sensitive to moisture and can undergo ring-opening reactions very readily. Palladium complexes with the ring-opened products from imidazolinium salts were isolated and characterized by X-ray crystallography. Theoretical studies confirmed that the imidazolinium salt has a higher propensity for the ring-opening reaction than the imidazolium counterpart. New mixed phosphine/carbene palladium complexes, Cis-[PdCl2(L)(PR3)] (L = L1 and L2; R = Ph. Cy). were successfully prepared. These complexes are highly robust as revealed by variable-temperature NMR spectroscopic studies and thermal gravimetric analysis. The structural and electronic properties of the new complexes on varying the carbene group (imidazol-2-ylidene group (unsaturated carbene) vs. imidazolin-2-ylidene (saturated carbene)) and the phosphine group (PPh3 vs. PCy 3) were studied in detail by X-ray crystallography, X-ray photoelectron spectroscopy, and theoretical calculations. The catalytic study reveals that Cis-[PdCl2(L2)-(PCy3)] is a competent PdII precatalyst for Suzuki coupling reactions, in which unreactive aryl chlorides can be applied as substrates.

One step from nitro to oxime: a convenient preparation of unsaturated oximes by the reduction of the corresponding vinylnitro compounds

A series of novel unsaturated oximes were conveniently prepared from the corresponding vinylnitro compounds by reduction with SnCl2·2H2O. The structures of the oximes were characterized by 1H and 13C NMR, IR and HRMS, and X-ray crystallography analysis of 1-(6-chloro-pyridin-3-ylmethyl)-4,5-dihydro-1H-imidazole-2-carbaldehyde oxime 2a reveals that, the hydroxyl group is arranged in a trans configuration. Some evidences from a brief investigation suggest that these oximes seem to be formed by reduction of the aci form of nitro aliphatic compounds.