579-72-6

Usage

Uses

Used in Pharmaceutical Industry:
2-(Dimethylamino)benzaldehyde is used as a key intermediate for the synthesis of various pharmaceuticals, leveraging its structural features to create complex organic molecules that possess therapeutic properties.
Used in Dye Industry:
In the dye industry, 2-(Dimethylamino)benzaldehyde is utilized as a precursor in the production of dyestuffs, contributing to the development of colorants for textiles, plastics, and other materials.
Used in Perfumery and Fragrance Industry:
2-(Dimethylamino)benzaldehyde is employed as a component in the formulation of perfumes and fragrances, enhancing the scent profiles of various products due to its unique chemical structure.
Used as a Reagent in Organic Chemistry:
2-(Dimethylamino)benzaldehyde is used as a reagent in the preparation of imines and other nitrogen-containing compounds, facilitating the synthesis of a wide range of organic molecules for research and industrial applications.
Caution:

InChI:InChI=1/C9H11NO/c1-10(2)9-6-4-3-5-8(9)7-11/h3-7H,1-2H3

Upstream product

• 271-58-9 anthranil 
• 77-78-1 dimethyl sulfate 
• 529-23-7 o-aminobenzaldehyde 
• 2591-86-8 N-Formylpiperidine 
• 121-69-7 N,N-dimethyl-aniline 
• 4707-56-6 (2-(dimethylamino)phenyl)methanol 
• 68-12-2 N,N-dimethyl-formamide 
• 100656-07-3 2-(Dimethylamino)benzaldehyd-dimethylacetal 
• 698-00-0 2-bromo-N,N-dimethylaniline 
• 320-65-0 ortho-fluoro-benzal chloride 
• 124-40-3 dimethyl amine 
• 100-58-3 phenylmagnesium bromide 
• 506-59-2 N,N-dimethylammonium chloride 
• 446-52-6 2-Fluorobenzaldehyde 

Downstream Products

• 92296-35-0 5-methyl-isoxazole-3-carboxylic acid (2-dimethylamino-benzylidene)-hydrazide 
• 58758-12-6 ortho-C₆H₄(NMe₂)CH=NC₆H₅ 
• 17506-94-4 1-<(piperidin-1-ylcarbonyl)carbonyl>piperidine 
• 121000-83-7 1-(2-Dimethylamino-phenyl)-2-piperidin-1-yl-ethane-1,2-dione 
• 100656-07-3 2-(Dimethylamino)benzaldehyd-dimethylacetal 
• 344873-87-6 (1H-Benzoimidazol-2-yl)-[1-(2-dimethylamino-phenyl)-meth-(E)-ylidene]-amine 
• 156054-89-6 2-(2-dimethylaminophenyl)-2-trimethylsilyloxyacetonitrile 
• 99052-43-4 5--2,2-dimethyl-4-phenyl-Δ³-1,3-oxazolin 
• 410069-57-7 (E)-2-chloro-1-[2-(N,N-dimethylamino)phenyl]ethene 
• 199679-45-3 3-(4-N,N-dimethylaminophenyl)acrylic acid 
• 876460-06-9 1-(2-dimethylaminophenyl)hex-2-yn-1-ol 
• 876460-05-8 1-(2-dimethylaminophenyl)-3-(4-methoxyphenyl)prop-2-yn-1-ol 

Relevant academic research and scientific papers

Rhodium(III)-Catalyzed Aldehyde C?H Activation and Functionalization with Dioxazolones: An Entry to Imide Synthesis

A rhodium(III)-based catalytic system has been used to develop a C?H bond activation of benzaldehyde derivatives and subsequent functionalization with dioxazolones in order to afford imides. The importance of the nature of the directing group to perform selectively the aldehydic C?H bond activation has been highlighted. The scope investigation showed that this transformation could be applied to various dioxazolones and many benzaldehyde derivatives as well as an acrolein derivative. Derivatization reactions of the imide products demonstrated the synthetic utility of this rhodium-catalyzed aldehydic C?H amidation.

Double Capture of Difluorocarbene by 2-Aminostyrenes Enables the Construction of 3-(2,2-Difluoroethyl)-2-fluoroindoles

We report herein an efficient strategy to construct 3-(2,2-difluoroethyl)-2-fluoroindoles from activated o-aminostyrenes with ethyl bromodi-fluoroacetate as a difluorocarbene source. Through double capture of a difluorocarbene, two different types of fluo

Development of TsDPEN based imine-containing ligands for the copper-catalysed asymmetric Kinugasa reaction

A novel class of chiralN,N,Nimine-containing ligands derived from TsDPEN (N-(p-tosyl)-1,2-diphenylethylene-1,2-diamine) has been developed and applied to the copper-catalyzed asymmetric Kinugasa reaction. The copper(ii) salt proved to be an efficient catalyst precursor, and it provides an efficient way to synthesize enantioenrichedcis-β-lactam. The pathway is air-tolerant and easily manipulated, and the ligands are easy to synthesize. A working model is proposed in which the stereocontrolling step is the [2 + 2] cycloaddition between ketene and imine to explain the observed stereoselectivities.

Substituent Effect Induces Emission Modulation of Stilbene Photoswitches by Spatial Tuning of the N/B Electronic Constraints

We present a family of stilbene derivatives (1-4) ortho-functionalized with an electron donor and acceptor. Their emission was tuned by donor substitutions, dictating charge transfer dependent on the N···B spatial separation. The steric reduction of subst

Reductive Cross-Coupling between Unactivated C(aryl)-N and C(aryl)-O Bonds by Chromium Catalysis Using a Bipyridyl Ligand

Reductive cross-coupling between two chemically inert bonds remains a great challenge in synthetic chemistry. We report here the reductive cross-coupling between unactivated C(aryl)-N and C(aryl)-O bonds that was achieved by chromium catalysis. The simple and inexpensive CrCl2 salt, combined with important bipyridyl ligand and magnesium reductant, shows high reactivity in the successive cleavage of C(aryl)-N bonds of aniline derivatives and C(aryl)-O bonds of aryl esters, allowing the cross-coupling of these two unactivated and different bonds to occur in a reductive fashion to form a C(aryl)-C(aryl) bond. Mechanistic studies by deuterium-labeling experiments indicate that the C(aryl)-N bonds in anilines are preferentially cleaved by reactive Cr species, in which the ligation of bipyridyl with Cr by adopting a coordination model in 1:1 ratio can be considered.

Novel [ONN] tridentate fourth subgroup metal complex as well as preparation method and application thereof

The invention provides a novel [ONN] tridentate fourth subgroup metal complex and a preparation method and application thereof. The novel [ONN] tridentate fourth subgroup metal complex has a structureas shown in formula I which is described in the specifi

BF3·OEt2-Promoted Propargyl Alcohol Rearrangement/[1,5]-Hydride Transfer/Cyclization Cascade Affording Tetrahydroquinolines

An efficient BF3·OEt2-mediated propargyl alcohol rearrangement/[1,5]-hydride transfer/cyclization cascade for the synthesis of tetrahydroquinoline derivatives has been described. The substituents adjacent to triple bonds play an important role in the formation of ketones (via [1,3]-hydroxyl shift) or alkenyl fluorides which are products of formal trans-carbofluorination of internal alkynes. This method provides a rapid access to diverse heterocycles in moderate to excellent yields.

Redox-Neutral Cascade Dearomatization of Indoles via Hydride Transfer: Divergent Synthesis of Tetrahydroquinoline-Fused Spiroindolenines

The redox-neutral cascade dearomatization of indoles with o-aminobenzaldehydes has been realized via the hydride transfer strategy, achieving the condition- A nd substrate-controlled divergent synthesis of tetrahydroquinoline-fused spiroindolenines. The integration of hydride transfer-involved C(sp3)-H functionalization with dearomatization provides a promising platform for the construction of structurally diverse molecules.

Chemical, computational and functional insights into the chemical stability of the Hedgehog pathway inhibitor GANT61

This work aims at elucidating the mechanism and kinetics of hydrolysis of GANT61, the first and most-widely used inhibitor of the Hedgehog (Hh) signalling pathway that targets Glioma-associated oncogene homologue (Gli) proteins, and at confirming the chemical nature of its bioactive form. GANT61 is poorly stable under physiological conditions and rapidly hydrolyses into an aldehyde species (GANT61-A), which is devoid of the biological activity against Hh signalling, and a diamine derivative (GANT61-D), which has shown inhibition of Gli-mediated transcription. Here, we combined chemical synthesis, NMR spectroscopy, analytical studies, molecular modelling and functional cell assays to characterise the GANT61 hydrolysis pathway. Our results show that GANT61-D is the bioactive form of GANT61 in NIH3T3 Shh-Light II cells and SuFu?/? mouse embryonic fibroblasts, and clarify the structural requirements for GANT61-D binding to Gli1. This study paves the way to the design of GANT61 derivatives with improved potency and chemical stability.

Tau-Centric Multitarget Approach for Alzheimer's Disease: Development of First-in-Class Dual Glycogen Synthase Kinase 3β and Tau-Aggregation Inhibitors

Several findings propose the altered tau protein network as an important target for Alzheimer's disease (AD). Particularly, two points of pharmacological intervention can be envisaged: inhibition of phosphorylating tau kinase GSK-3β and tau aggregation process. On the basis of this consideration and on our interest in multitarget paradigms in AD, we report on the discovery of 2,4-thiazolidinedione derivatives endowed with such a profile. 28 and 30 displayed micromolar IC50 values toward GSK-3β, together with the capacity of inhibiting AcPHF6 aggregation of 60% and 80% at 10 μM, respectively. In addition, they showed PAMPA-BBB permeability, together with a suitable cellular safety profile. 30 also displayed inhibition of both K18 and full-length tau aggregations. Finally, both compounds were able to improve cell viability in an okadaic acid-induced neurodegeneration cell model. To the best of our knowledge, 28 and 30 are the first balanced, nontoxic, dual-acting compounds hitting tau cascade at two different hubs.