24197-95-3

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
4-[2-(DIMETHYLAMINO)ETHOXY]BENZONITRILE is used as a building block in the synthesis of pharmaceuticals and agrochemicals for its unique chemical structure that can contribute to the development of novel therapeutic agents and crop protection products.
Used in Organic Electronics and Optoelectronics:
In the field of organic electronics and optoelectronics, 4-[2-(DIMETHYLAMINO)ETHOXY]BENZONITRILE is used as a material with high electron affinity and good electron transport properties, making it a promising candidate for applications in electronic devices and optoelectronic systems.
Safety Considerations:
Due to its toxic and potentially harmful nature, 4-[2-(DIMETHYLAMINO)ETHOXY]BENZONITRILE must be handled with care and in compliance with safety regulations to ensure the safety of researchers and the environment.

InChI:InChI=1/C11H14N2O/c1-13(2)7-8-14-11-5-3-10(9-12)4-6-11/h3-6H,7-8H2,1-2H3

Upstream product

• 623-03-0 4-Cyanochlorobenzene 
• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 1197-19-9 4-cyano-N,N-dimethylaniline 
• 767-00-0 4-cyanophenol 
• 105-58-8 Diethyl carbonate 
• 4584-46-7 (2-chloroethyl)dimethylamine hydrochloride 
• 107-99-3 2-(dimethylamino)ethyl chloride 

Downstream Products

• 20059-73-8 4-<2-(dimethylamino)ethoxy>benzylamine 

Relevant academic research and scientific papers

Mustard Carbonate Analogues as Sustainable Reagents for the Aminoalkylation of Phenols

N,N-dialkyl ethylamine moiety can be found in numerous scaffolds of macromolecules, catalysts, and especially pharmaceuticals. Common synthetic procedures for its incorporation in a substrate relies on the use of a nitrogen mustard gas or on multistep syntheses featuring chlorine hazardous/toxic chemistry. Reported herein is a one-pot synthetic approach for the easy introduction of aminoalkyl chain into different phenolic substrates through dialkyl carbonate (β-aminocarbonate) chemistry. This new direct alcohol substitution avoids the use of chlorine chemistry, and it is efficient on numerous pharmacophore scaffolds with good to quantitative yield. The cytotoxicity via MTT of the β-aminocarbonate, key intermediate of this synthetic approach, was also evaluated and compared with its alcohol precursor.

From Anilines to Aryl Ethers: A Facile, Efficient, and Versatile Synthetic Method Employing Mild Conditions

We have developed a simple and direct method for the synthesis of aryl ethers by reacting alcohols/phenols (ROH) with aryl ammonium salts (ArNMe3+), which are readily prepared from anilines (ArNR′2, R′=H or Me). This reaction proceeds smoothly and rapidly (within a few hours) at room temperature in the presence of a commercially available base, such as KOtBu or KHMDS, and has a broad substrate scope with respect to both ROH and ArNR′2. It is scalable and compatible with a wide range of functional groups.

Acridone-based inhibitors of inosine 5′-monophosphate dehydrogenase: Discovery and SAR leading to the identification of N-(2-(6-(4-ethylpiperazin-1- yl)pyridin-3-yl)propan-2-yl)-2-fluoro-9-oxo-9,10-dihydroacridine-3-carboxamide (BMS-566419)

Inosine monophosphate dehydrogenase (IMPDH), a key enzyme in the de novo synthesis of guanosine nucleotides, catalyzes the irreversible nicotinamide-adenine dinucleotide dependent oxidation of inosine-5′- monophosphate to xanthosine-5′-monophosphate. Mycophenolate Mofetil (MMF), a prodrug of mycophenolic acid, has clinical utility for the treatment of transplant rejection based on its inhibition of IMPDH. The overall clinical benefit of MMF is limited by what is generally believed to be compound-based, dose-limiting gastrointestinal (GI) toxicity that is related to its specific pharmacokinetic characteristics. Thus, development of an IMPDH inhibitor with a novel structure and a different pharmacokinetic profile may reduce the likelihood of GI toxicity and allow for increased efficacy. This article will detail the discovery and SAR leading to a novel and potent acridone-based IMPDH inhibitor 4m and its efficacy and GI tolerability when administered orally in a rat adjuvant arthritis model.

METHOD FOR PREPARING 4-[2-(DIMETHYLAMINO)ETHOXY]BENZYLAMINE AS ITOPRIDE HYDROCLORIDE SALT MEDIATE

The present invention relates to a novel method for preparing an itopride·hydrochloride mediate of the formula 1, which is useful for digestive tract activator, and more particularly, the present invention provides with a method for preparing 4-[2-(dimethylamino)ethoxy]benzylamine of the formula 1, an itopride·hydrochloride mediate, whereby being capable of manufacturing in a high yield and lowering cost through a simple purification and a selective reaction, and the method is harmless and safe to human and environment due to not generating toxic gas. And specially, a super-high pressure hydrogenation and a reduction reaction using a metal catalyst are not carried out, therefore, it is very safe method, and also special manufacturing equipments are not needed.

METHOD FOR PRODUCING AMINOALKOXY BENZYLAMINES AND AMINOALKOXY BENZONITRILES AS INTERMEDIATES

The invention relates to methods for producing 4-[aminoalkoxy]benzylamines of general formula (I) by means of catalytic hydrogenation of 4-[aminoalkoxy]benzonitriles of general formula (II). In the compounds of general formulae (I) and (II), R1 represents C1-C8 alkylene, and R2 and R3 independently represent C1-C8 alkyl or are linked to form a ring which can also contain a heteroatom. The hydrogenation is carried out at increased pressure and increased temperatures. The invention also relates to a method for producing the intermediate (II).