40172-04-1

Basic information

• Product Name: 2-(4-CHLORO-BENZYLAMINO)-ETHANOL
• Synonyms: 2-(4-CHLORO-BENZYLAMINO)-ETHANOL
• CAS NO: 40172-04-1
• Molecular Formula: C₉H₁₂ClNO
• Molecular Weight: 185.65
• Mol File: 40172-04-1.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-CHLORO-BENZYLAMINO)-ETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-CHLORO-BENZYLAMINO)-ETHANOL(40172-04-1)
• EPA Substance Registry System: 2-(4-CHLORO-BENZYLAMINO)-ETHANOL(40172-04-1)

Safety Data

• Hazardous Substances Data: 40172-04-1(Hazardous Substances Data)

Usage

Structure

A derivative of ethanol with a benzylamine group and a chlorine atom attached to the benzene ring

Usage

Commonly used in the pharmaceutical and chemical industries as a building block for the synthesis of various drugs and organic compounds

Applications

Potential applications in the development of new medications and as a reagent in organic synthesis, as well as in research and development activities for its structural and functional properties

Unique properties

Due to its chemical structure and functional groups, 2-(4-CHLORO-BENZYLAMINO)-ETHANOL possesses unique properties that make it valuable for a wide range of applications in various scientific and industrial fields.

Upstream product

• 141-43-5 ethanolamine 
• 622-95-7 4-chlorobenzyl bromide 
• 104-88-1 4-chlorobenzaldehyde 
• 16327-95-0 p-chloro-N-benzilidine ethanolamine 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 

Downstream Products

• 105905-67-7 chloro-acetic acid-[(4-chloro-benzyl)-(2-hydroxy-ethyl)-amide] 
• 1018909-08-4 tert-butyl (2-azidoethyl)(4-chlorobenzyl)carbamate 
• 1018909-30-2 tert-butyl 4-chlorobenzyl(2'-(methylamino)ethyl)carbamate 
• 1018909-28-8 tert-butyl 4-chlorobenzyl(2'-oxoethyl)carbamate 
• 1018909-16-4 tert-butyl (2-aminoethyl)(4-chlorobenzyl)carbamate 
• 115-22-0 3-Hydroxy-3-methyl-2-butanone 
• 6317-28-8 3-(4-chlorobenzyl)oxazolidin-2-one 
• 1391074-47-7 1-(2-benzo[b]thiophen-3-yl-acetyl)-2-methyl-azetidine-2-carboxylic acid (4-chloro-benzyl)-(2-hydroxy-ethyl)-amide 
• 1397956-79-4 3-(((4-chlorobenzyl)(2-hydroxyethyl)amino)methyl)-5-(cyclohexylmethoxy)-4H-chromen-4-one 
• 1352732-59-2 N-tert-butyl-7-(4-chlorobenzyl)-3-oxo-2,3,5,6,7,8-hexahydrobenzo[i][1,4,7]dioxazecine-8-carboxamide 
• 1352732-55-8 5-(4-chlorobenzyl)-N-cyclohexyl-1-oxo-3,4,5,6-tetrahydrobenzo[f][1,4]oxazocine-6-carboxamide 
• 441314-95-0 N,N'-bis(p-chlorobenzyl)piperazine 
• 1003887-54-4 (R)-tert-butyl 2-((4-chlorobenzyl)(2-hydroxyethyl)carbamoyl)pyrrolidine-1-carboxylate 

Relevant articles and documents

Discovery of benzimidazole analogs as a novel interleukin-5 inhibitors

A series of novel hydroxyethylaminomethylbenzimidazole analogs 5a-y were synthesized and evaluated for their IL-5 inhibitory activity using pro-B Y16 cell line. Among them, 2-(((4-(cyclohexylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)amino)butan-1-ol (5e, 94.3% inhibition at 30 μM, IC50 = 3.5 μM, cLogP = 4.132) and 3-cyclohexyl-2-(((4-(cyclohexylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)amino) propan-1-ol (5k, 94.7% inhibition at 30 μM, IC50 = 5.0 μM, cLogP = 6.253) showed the most potent inhibitory activity. The essential feature of SAR (Fig. 5) indicated that the chromenone ring can be replaced by a benzimidazole ring to maintain the inhibitory activity. In addition, the hydroxyethylaminomethyl group was suitable for the IL-5 inhibitory activity. Moreover, the hydrophobic substituents on carbon play an important role in the IL-5 inhibitory activity of these analogs. However, N-substituted analogs did not improve inhibitory activity. In addition, MTT assay of 5e and 5k with normal B lymphoblasts revealed that they had no significant effects on cell viability.

AgI/TMG-Promoted Cascade Reaction of Propargyl Alcohols, Carbon Dioxide, and 2-Aminoethanols to 2-Oxazolidinones

Chemical valorization of CO2 to access various value-added compounds has been a long-term and challenging objective from the viewpoint of sustainable chemistry. Herein, a one-pot three-component reaction of terminal propargyl alcohols, CO2, and 2-aminoethanols was developed for the synthesis of 2-oxazolidinones and an equal amount of α-hydroxyl ketones promoted by Ag2O/TMG (1,1,3,3-tetramethylguanidine) with a TON (turnover number) of up to 1260. By addition of terminal propargyl alcohol, the thermodynamic disadvantage of the conventional 2-aminoethanol/CO2 coupling was ameliorated. Mechanistic investigations including control experiments, DFT calculation, kinetic and NMR studies suggest that the reaction proceeds through a cascade pathway and TMG could activate propargyl alcohol and 2-aminoethanol through the formation of hydrogen bonds and also activate CO2.

Discovery of highly potent and selective inhibitors of neuronal nitric oxide synthase by fragment hopping

Selective inhibition of neuronal nitric oxide synthase (nNOS) has been shown to prevent brain injury and is important for the treatment of various neurodegenerative disorders. This study shows that not only greater inhibitory potency and isozyme selectivity but more druglike properties can be achieved by fragment hopping. On the basis of the structure of lead molecule 6, fragment hopping effectively extracted the minimal pharmacophoric elements in the active site of nNOS for ligand hydrophobic and steric interactions and generated appropriate lipophilic fragments for lead optimization. More potent and selective inhibitors with better druglike properties were obtained within the design of 20 derivatives (compounds 7-26). Our structure - based inhibitor design for nNOS and SAR analysis reveal the robustness and efficiency of fragment hopping in lead discovery and structural optimization, which implicates a broad application of this approach to many other therapeutic targets for which known druglike small-molecule modulators are still limited.