136-80-1

Usage

Uses

Used in Pharmaceutical Industry:
2-(O-Tolylamino)ethanol is used as a chemical intermediate for the synthesis of pharmaceuticals, contributing to the development of new drugs and medicinal compounds. Its unique structure allows for versatile chemical reactions, facilitating the creation of a wide range of therapeutic agents.
Used in Dye Synthesis:
In the dye industry, 2-(O-Tolylamino)ethanol is utilized as a precursor in the production of various dyes. Its chemical properties enable the formation of diverse colorants used in textiles, printing, and other applications requiring coloration.
Used in Research and Development:
2-(O-Tolylamino)ethanol is employed in research and development efforts to explore and create novel chemical compounds. Its reactivity and structural features make it a valuable component in the design and synthesis of new organic materials with potential applications in various industries.

InChI:InChI=1/C9H13NO/c1-8-4-2-3-5-9(8)10-6-7-11/h2-5,10-11H,6-7H2,1H3

Upstream product

• 75-21-8 oxirane 
• 95-53-4 o-toluidine 
• 90869-76-4 N-(o-tolyl)-(2-chloroethyl) carbamate 
• 107-07-3 2-chloro-ethanol 
• 52316-60-6 2-hydroxyethylchloramine 
• 108-88-3 toluene 
• 624-76-0 Iodoethanol 
• 107-21-1 ethylene glycol 
• 627-11-2 2-Chloroethyl chloroformate 
• 37072-63-2 N-(2-methylphenyl)oxazolidin-2-one 
• 95-46-5 2-methylphenyl bromide 
• 141-43-5 ethanolamine 

Downstream Products

• 3367-47-3 1,4-di-o-tolyl-piperazine 
• 78182-25-9 sulfuric acid mono-(2-o-toluidino-ethyl ester) 
• 28690-16-6 phenyl-(3-o-tolyl-thiazolidin-2-yliden)-amine 
• 858844-90-3 N'-benzoyl-N-(2-hydroxy-ethyl)-N-o-tolyl-thiourea 
• 28690-12-2 3-(o-tolyl)-2-thiazolidinethione 
• 28819-62-7 2-methyl-3-o-tolyl-oxazolidine 

Relevant academic research and scientific papers

Green synthesis of N-(2-hydroxyethyl)anilines by the selective alkylation reaction in H2O

Based on our previous work, a safer and more sustainable protocol for the synthesis of N-(2-Hydroxyethyl)anilines has been developed. The synthesis included the selective alkylation reaction of aniline with 2-chloroethanol in H2O, eliminating the need for any catalysts and solvents during synthesis. Comparing with our previous work, the salient features of this methodology are eco-friendliness, economic benefit, and the ease of obtaining target compounds. The selective alkylation reaction in H2O is amenable to scale-up for the synthesis of N-(2-Hydroxyethyl)anilines.

A method for the preparation of indole compounds and use thereof (by machine translation)

A method for the preparation of indole compounds and its application, relates to the field of organic synthesis, the preparation method by aniline compound with ethylene oxide in the 1st under the action of catalyst reaction to obtain N - hydroxy ethyl aniline compound, then the N - hydroxy ethyl aniline compound with the aniline of the compounds in the 2nd reaction under the action of catalyst preparation indole compounds. The preparation method step is simple, requires only two-step reaction can efficiently yield to obtain the indole compound, its route is reasonable in design, simple steps, easy operation, low cost, and is suitable for industrial mass production. The preparation method is applied to the preparation of pharmaceutical in the indole structure, can improve the yield of the medicament, the medicine of the large-scale production. (by machine translation)

β-Amino alcohols from anilines and ethylene glycol through heterogeneous Borrowing Hydrogen reaction

Borrowing Hydrogen (BH), also called Hydrogen Autotransfer (HA), reaction with neat ethylene glycol represents a key step in the preparation of β-amino alcohols. However, due to the stability of ethylene glycol, mono-activation has rarely been achieved. Herein, a combination of Pd/C and ZnO is reported as heterogeneous catalyst for this BH/HA reaction. This system results in an extremely air and moisture stable, and economic catalyst able to mono-functionalize ethylene glycol in water, without further activation of the diol. In this work, different diols and aromatic amines have been explored affording a new approach towards amino alcohols. This study reveals how the combination of two solid species can afford interesting catalytic properties in heterogeneous phase. ZnO activates ethylene glycol while Pd/C is the responsible of the BH/HA cycle. This catalytic system has also been found useful to dehydrogenate indoles affording indolines that undergo in situ BH/HA cycle prior to re-aromatization, representing a tandem heterogeneous process.

Palladium-catalyzed intramolecular carbene insertion into C(sp3)-H bonds

A palladium-catalyzed carbene insertion into C(sp3)-H bonds leading to pyrrolidines was developed. The coupling reaction can be catalyzed by both Pd0 and PdII, is regioselective, and shows a broad functional group tolerance. This reaction is the first example of palladium-catalyzed C(sp3)-C(sp3) bond assembly starting from diazocarbonyl compounds. DFT calculations revealed that this direct C(sp3)-H bond functionalization reaction involves an unprecedented concerted metalation-deprotonation step. Pd in action: Palladium has been used to catalyze the C(sp3)-H insertion of metal carbenoids derived from α-diazoesters to form pyrrolidines through intramolecular assembly of C(sp3)-C(sp3) bonds. A reaction mechanism involving a metalation-deprotonation step instead of the usual concerted but asynchronous process is proposed.

Bis-aryl urea derivatives as potent and selective LIM kinase (Limk) inhibitors

The discovery/optimization of bis-aryl ureas as Limk inhibitors to obtain high potency and selectivity and appropriate pharmacokinetic properties through systematic SAR studies is reported. Docking studies supported the observed SAR. Optimized Limk inhibitors had high biochemical potency (IC50 400-fold), potent inhibition of cofilin phosphorylation in A7r5, PC-3, and CEM-SS T cells (IC50 1 μM), and good in vitro and in vivo pharmacokinetic properties. In the profiling against a panel of 61 kinases, compound 18b at 1 μM inhibited only Limk1 and STK16 with ≥80% inhibition. Compounds 18b and 18f were highly efficient in inhibiting cell-invasion/migration in PC-3 cells. In addition, compound 18w was demonstrated to be effective on reducing intraocular pressure (IOP) on rat eyes. Taken together, these data demonstrated that we had developed a novel class of bis-aryl urea derived potent and selective Limk inhibitors.

Green and efficient protocol for the synthesis of N-(2-hydroxyethyl)anilines by the alkylation reaction in ionic liquid

A green and efficient protocol for the synthesis of N-(2-hydroxyethyl)anilines by the selective alkylation reaction in ionic liquid [BMIM]BF4 (1-butyl-3-methylimidazolium tetrafluoroborate) has been developed, eliminating the need for toxic and expensive catalysts and volatile organic solvents. The effects of the amount of ionic liquid, temperature, time, and substrate structure on the reaction were investigated. The conversion and selectivity of N-(2-hydroxyethyl)anilines obtained in ionic liquid [BMIM]BF4 are significantly increased in comparison to those traditional methods. Furthermore, the ionic liquid could be easily separated and reused at least five times. It provided a simple and efficient alternative way for the industrial synthesis of N-(2-hydroxyethyl)anilines.

Solvent-free copper-catalyzed N-arylation of amino alcohols and diamines with aryl halides

A simple and mild method for the coupling of aryl halides with amino alcohols and diamines is described. The reactions can be performed under ligand-free and solvent-free conditions, and generate the products in good yield.

INDAZOLEPROPIONIC ACID AMIDE COMPOUND

Disclosed is a compound which is useful in preventing and treating cardiac arrhythmia such as atrial fibrillation. A compound represented by formula (1) or a pharmaceutically acceptable salt of the same. In formula (1), ring X represents benzene or pyridine; R1 represents an optionally substituted alkyl group; R2 represents an optionally substituted aryl group, an optionally substituted heterocyclic group, an optionally substituted arylalkyl group or an optionally substituted heterocyclic group-substituted alkyl group; R3, R4, R5, R6, R7, R8 and R9 represent each hydrogen or an alkyl group, provided that R3 and R5 may be bonded to each other to form, together with the carbon atom adjacent thereto, a cycloalkyl group; and m represents 0 or 1.

One-pot synthesis of unsymmetrical N-heterocyclic carbene ligands from N-(2-iodoethyl)arylamine salts

Image Presented An approach that provides symmetrical, unsymmetrical, and asymmetric N-heterocyclic carbene (NHC) ligands is reported. Reaction of iodoethanol with aniline provides N-(2-iodoethyl)arylamine salts that are then converted to the corresponding iodide. Reaction with aliphatic or aromatic amines followed by triethyl orthoformate was used to provide 26 different NHC ligands.