699-04-7

Usage

Uses

Used in Organic Synthesis:
N-Methyl-N-(4-methylbenzyl)amine is used as a reagent in organic synthesis for its ability to facilitate various chemical reactions, enhancing the efficiency and selectivity of the processes.
Used in Catalysts for Reactions:
As a catalyst, N-Methyl-N-(4-methylbenzyl)amine is employed to accelerate the rate of chemical reactions in different industries, improving the overall yield and reducing the time required for the reactions to complete.
Used in Epoxy Resin Production:
N-Methyl-N-(4-methylbenzyl)amine is used as a curing agent in the production of epoxy resins, which are essential components in coatings, adhesives, and composite materials due to their high strength and durability.
Used in Pharmaceutical and Agrochemical Synthesis:
In the pharmaceutical and agrochemical industries, N-Methyl-N-(4-methylbenzyl)amine is utilized in the synthesis of various active ingredients, contributing to the development of new drugs and pesticides.
Used in Dye and Pigment Production:
N-Methyl-N-(4-methylbenzyl)amine is used as a reagent in the production of dyes and pigments, playing a crucial role in the creation of vibrant colors and shades for various applications.
Used in Polymer Manufacturing:
In the polymer industry, N-Methyl-N-(4-methylbenzyl)amine is employed in the manufacturing of certain polymers, contributing to the development of new materials with specific properties and applications.
Used as a Stabilizer in Plastics and Rubbers Production:
N-Methyl-N-(4-methylbenzyl)amine is used as a stabilizer in the production of plastics and rubbers to enhance their resistance to degradation, ensuring longer-lasting and more reliable products.
It is important to handle N-Methyl-N-(4-methylbenzyl)amine with care, as it is flammable and can cause skin and respiratory irritation upon contact. Proper safety measures should be taken during its use to minimize potential risks.

InChI:InChI=1/C9H13N/c1-8-3-5-9(6-4-8)7-10-2/h3-6,10H,7H2,1-2H3/p+1

Upstream product

• 17972-13-3 p-methylbenzylidene-methylamine 
• 104-87-0 4-methyl-benzaldehyde 
• 74-89-5 methylamine 
• 104-82-5 4-Methylbenzyl chloride 
• 104-81-4 4-Methylbenzyl bromide 
• 4052-88-4 4-methyl-N,N-dimethylbenzylamine 
• 80-48-8 methyl p-toluene sulfonate 
• 104-84-7 para-methylbenzylamine 
• 80-18-2 Methyl benzenesulfonate 
• 6214-20-6 methyl 4-nitrobenzenesulfonate 
• 15481-45-5 methyl p-chlorobenzenesulphonate 
• 53699-34-6 (E)-N-methyl[(4-methylphenyl)methylidene]amine 
• 108-88-3 toluene 
• 959922-04-4 N-(3-methoxyphenylmethyl)carbamic acid ethyl ester 

Downstream Products

• 29524-27-4 dichloro-acetic acid-[methyl-(4-methyl-benzyl)-amide] 
• 861342-35-0 methyl-(4-methyl-benzyl)-(4-phenyl-benzyl)-amine 
• 876476-20-9 methyl-(3-methyl-benzyl)-(4-methyl-benzyl)-amine 
• 857825-44-6 N-methyl-N-(4-methyl)benzyl-(4-methoxy)benzylamine 
• 854670-38-5 [methyl-(4-methyl-benzyl)-amino]-acetone 
• 99812-81-4 6,6-Dimethyl-2-[methyl-(4-methyl-benzyl)-amino]-4-oxo-cyclohex-2-enecarbonitrile 
• 111291-48-6 C₁₆H₁₆F₃NO₃S 
• 128667-37-8 6-{2-Hydroxy-3-[methyl-(4-methyl-benzyl)-amino]-propoxy}-1H-quinolin-2-one 
• 74654-98-1 4-(2-Cyano-phenyl)-2-diethoxymethyl-6-methyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-{2-[methyl-(4-methyl-benzyl)-amino]-ethyl} ester 
• 62783-50-0 N-nitroso-N-(p-methylbenzyl)methylamine 
• 143666-80-2 N-Methyl-N-(4-methyl-benzyl)-2-(4-nitro-phenoxy)-acetamide 
• 17972-13-3 p-methylbenzylidene-methylamine 
• 203861-67-0 N-methyl-4-tolylnitrone 
• 104-85-8 para-methylbenzonitrile 

Relevant academic research and scientific papers

Discovery of novel small-molecule inhibitors of BRD4 using structure-based virtual screening

Bromodomains (BRDs) are epigenetic readers that recognize acetylated-lysine (KAc) on proteins and are implicated in a number of diseases. We describe a virtual screening approach to identify BRD inhibitors. Key elements of this approach are the extensive design and use of substructure queries to compile a set of commercially available compounds featuring novel putative KAc mimetics and docking this set for final compound selection. We describe the validation of this approach by applying it to the first BRD of BRD4. The selection and testing of 143 compounds lead to the discovery of six novel hits, including four unprecedented KAc mimetics. We solved the crystal structure of four hits, determined their binding mode, and improved their potency through synthesis and the purchase of derivatives. This work provides a validated virtual screening approach that is applicable to other BRDs and describes novel KAc mimetics that can be further explored to design more potent inhibitors.

Selective synthesis of mono- and di-methylated amines using methanol and sodium azide as C1 and N1 sources

A Ru(ii) complex mediated synthesis of various N,N-dimethyl and N-monomethyl amines from organic azides using methanol as a methylating agent is reported. This methodology was successfully applied for a one-pot reaction of bromide derivatives and sodium azide in methanol. Notably, by controlling the reaction time several N-monomethylated and N,N-dimethylated amines were synthesized selectively. The practical applicability of this tandem process was revealed by preparative scale reactions with different organic azides and synthesis of an anti-vertigo drug betahistine. Several kinetic experiments and DFT studies were carried out to understand the mechanism of this transformation.

Design, synthesis, and biological evaluation of a series of resorcinol-based N-benzyl benzamide derivatives as potent Hsp90 inhibitors

Heat shock protein 90 (Hsp90) is a ubiquitous molecular chaperone that is responsible for the stabilization and maturation of many oncogenic proteins. Therefore, Hsp90 has emerged as an attractive target in the field of cancer chemotherapy. In this study, we report the design, synthesis, and biological evaluation of a series of Hsp90 inhibitors. In particular, compound 30f shows a significant Hsp90α inhibitory activity with IC50 value of 5.3 nM and an excellent growth inhibition with GI50 value of 0.42 μM against non-small cell lung cancer cells, H1975. Compound 30f effectively reduces the expression levels of Hsp90 client proteins including Her2, EGFR, Met, Akt, and c-Raf. Consequently, compound 30f promotes substantial cleavages of PARP, Caspase 3, and Caspase 8, indicating that 30f induces cancer cell death via apoptotic pathway. Moreover, cytochrome P450 assay indicates that compound 30f has weak inhibitory effect on the activities of five major P450 isoforms (IC50 > 5 μM for 1A2, 2C9, 2C19, 2D6, and 3A), suggesting that clinical interactions between 30f and the substrate drugs of the five major P450 isoforms are not expected. Compound 30f also inhibits the tumor growth in a mouse xenograft model bearing subcutaneous H1975 without noticeable abnormal behavior and body weight changes. The immunostaining and western immunoblot analysis of EGFR, Met, Akt in xenograft tissue sections of tumor further demonstrate a good agreement with the in vitro results.

Selective Monomethylation of Amines with Methanol as the C1 Source

The N-monomethyl functionality is a common motif in a variety of synthetic and natural compounds. However, facile access to such compounds remains a fundamental challenge in organic synthesis owing to selectivity issues caused by overmethylation. To address this issue, we have developed a method for the selective, catalytic monomethylation of various structurally and functionally diverse amines, including typically problematic primary aliphatic amines, using methanol as the methylating agent, which is a sustainable chemical feedstock. Kinetic control of the aliphatic amine monomethylation was achieved by using a readily available ruthenium catalyst at an adequate temperature under hydrogen pressure. Various substrates including bio-related molecules and pharmaceuticals were selectively monomethylated, demonstrating the general utility of the developed method.

Tandem C(sp3)?H Arylation/Oxidation and Arylation/Allylic Substitution of Isoindolinones

Isoindolinones comprise an important class of medicinally active compounds. Herein we report a straightforward functionalization of isoindolinones with aryl bromides (22 examples) using a palladium(II) acetate/NIXANTPHOS-based catalyst system. Additionally 3-aryl-3-hydroxyisoindolinone derivatives, which exhibit anti-tumor activity, can be accessed via a tandem reaction. Thus, when the arylation product is exposed to air under basic conditions, in situ oxidation takes place to install the 3-hydroxy group. Furthermore, a tandem arylation/allylic substitution reaction is advanced in which both the arylation and allylic substitution are catalyzed by the same palladium catalyst. Finally, a tandem arylation/alkylation procedure is presented. These tandem reactions enable the synthesis of a variety of structurally diverse isoindolinone derivatives from common starting materials. (Figure presented.).

4-Phenyl tetrahydroisoquinolines as dual norepinephrine and dopamine reuptake inhibitors

Novel 4-phenyl tetrahydroisoquinolines that inhibit both dopamine and norepinephrine transporters were designed and prepared. In this Letter, we describe the synthesis, in vitro activity and associated structure-activity relationships of this series. We also report the ex vivo NET occupancy of a representative compound, 41.

Highly enantioselective synthesis of tetrahydroquinolines via cobalt(II)-catalyzed tandem 1,5-hydride transfer/cyclization

A chiral catalyst prepared from N,N′-dioxide and Co(BF 4)2·6H2O was applied in the asymmetric hydride transfer initiated cyclization reaction, giving optically active tetrahydroquinolines in good yields with high enantioselectivities under mild reaction conditions. Meanwhile, in light of the absolute configuration of the product, a possible working model was proposed to explain the origin of the activation and asymmetric induction.

NOVEL PROTEIN TYROSINE PHOSPHATASE - IB INHIBITORS

The present invention relates to the novel compounds of the general formula (I), wherein the symbols are same as described in specification, their pharmaceutically acceptable salts, their tautomeric forms, their stereoisomers, pharmaceutical compositions containing them, to process and intermediates for the preparation of the above said compounds, having the utility of these compounds in medicine and to methods for their therapeutic use, and their use in the treatment of diabetes and related diseases.

NOVEL PROTEIN TYROSINE PHOSPHATASE - IB INHIBITORS

The present invention relates to the novel compounds of the general formula (I), wherein the symbols are same as described in specification, their pharmaceutically acceptable salts, pharmaceutical compositions containing them, to process and intermediates for the preparation of the above said compounds, having the utility of these compounds in medicine and to methods for their therapeutic use, and their use in the treatment of metabolic disorders.

Antimycobacterial activity of new 3,5-disubstituted 1,3,4-oxadiazol-2(3H)-one derivatives. Molecular modeling investigations

3H-1,3,4-Oxadiazol-2-one derivatives were synthesized and tested for their in vitro antimycobacterial activity. Oxadiazolone derivatives showed an interesting antimycobacterial activity against the reference strain of Mycobacterium tuberculosis H37Rv. Molecular modeling investigations were performed and showed that the active compounds possess all necessary features to target the protein active site of the mycobacterial cytochrome P450-dependent sterol 14α-demethylase in the sterol biosynthesis pathway as the calculated free energy of binding were in agreement with the corresponding MIC values.