94-87-1

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2-(o-chloroanilino)ethanol is used as a key intermediate in the synthesis of a range of pharmaceuticals and agrochemicals. Its unique structure allows for the development of new compounds with potential therapeutic and pesticidal properties.
Used in Antibacterial Applications:
Leveraging its antibacterial properties, 2-(o-chloroanilino)ethanol is studied for its potential use in treating bacterial infections. Its ability to target and inhibit bacterial growth makes it a promising candidate for new antimicrobial agents.
Used in Dye and Pigment Production:
2-(o-chloroanilino)ethanol also serves as an intermediate in the production of dyes and pigments, contributing to the coloration and stability of various products in the textile, paint, and printing industries.
Safety Considerations:
It is crucial to handle 2-(o-chloroanilino)ethanol with care due to its potential toxicity if ingested or inhaled. Additionally, it may cause skin and eye irritation, necessitating proper safety measures during its use and disposal.

InChI:InChI=1/C8H10ClNO/c9-7-3-1-2-4-8(7)10-5-6-11/h1-4,10-11H,5-6H2

Upstream product

• 95-51-2 o-chloroaniline 
• 107-07-3 2-chloro-ethanol 
• 627-11-2 2-Chloroethyl chloroformate 
• 101869-85-6 3-(2-chlorophenyl)-oxazolidin-2-one 
• 25209-83-0 (2-Chloro-phenyl)-carbamic acid 2-chloro-ethyl ester 
• 75-21-8 oxirane 

Downstream Products

• 65018-24-8 1,4-bis-(2-chloro-phenyl)-piperazine 
• 561277-25-6 1-(3-benzyloxy-4-methoxy-phenyl)-3-(2-chloro-phenyl)-imidazolidin-2-one 
• 561277-16-5 N-(3-benzyloxy-4-methoxy-phenyl)-N'-(2-chloro-phenyl)-ethane-1,2-diamine 
• 561277-28-9 1-(2-chloro-phenyl)-3-(3-hydroxy-4-methoxy-phenyl)-imidazolidin-2-one 
• 43047-20-7 2-[2-chloro-4-(4-nitro-phenylazo)-anilino]-ethanol 

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.

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.

A series of bisaryl imidazolidin-2-ones has shown to be selective and orally active 5-HT2C receptor antagonists

Bisaryl cyclic ureas have been identified as high affinity 5-HT 2C receptor antagonists with selectivity over 5-HT2A and 5-HT2B. Compounds such as 8 and 22 have shown oral activity in a centrally mediated pharmacodynamic model of 5-HT2C function in rodents.