79668-76-1

Basic information

• Product Name: 3-(3-CHLORO-PROPOXY)ANILINE
• Synonyms: 3-(3-CHLORO-PROPOXY)ANILINE
• CAS NO: 79668-76-1
• Molecular Formula: C₉H₁₂ClNO
• Molecular Weight: 185.6507
• Mol File: 79668-76-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 332.3 °C at 760 mmHg
• Flash Point: 154.8 °C
• Appearance: /
• Density: 1.159 g/cm³
• PKA: 4.16±0.10(Predicted)
• CAS DataBase Reference: 3-(3-CHLORO-PROPOXY)ANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3-CHLORO-PROPOXY)ANILINE(79668-76-1)
• EPA Substance Registry System: 3-(3-CHLORO-PROPOXY)ANILINE(79668-76-1)

Safety Data

• Hazardous Substances Data: 79668-76-1(Hazardous Substances Data)

Upstream product

• 7440-02-0 nickel 
• 132636-13-6 1-(3-chloropropoxy)-3-nitrobenzene 
• 109-70-6 1.3-chlorobromopropane 
• 591-27-5 m-Hydroxyaniline 

Downstream Products

• 1453205-36-1 C₁₆H₁₆INO₂ 
• 1453205-10-1 C₁₉H₂₀N₂O₂ 
• 1453205-11-2 C₂₀H₂₂N₂O₂ 
• 925920-62-3 3-[3-(morpholino)propoxy]benzenamine 
• 1135-26-8 3-[3-(dimethylamine)propoxy]benzenamine 
• 950752-48-4 [3-(3-chloro-propoxy)-phenyl]-(4-chloro-pyrimidin-2-yl)-amine 

Relevant articles and documents

Design, synthesis and biological evaluation of selected 3-[3-(amino) propoxy] benzenamines as acetylcholinesterase inhibitors

The present paper describes design, synthesis, and biological evaluation of a series of some 3-[3-(amino)propoxy]benzenamines as acetylcholinesterase inhibitors using mice as a model and piracetam as a reference drug. The structures of these compounds were confirmed by spectral analysis and compounds were tested for memory enhancing activity using elevated plus maze test and acetylcholinesterase inhibitory assay. The inhibitory range of synthesized compounds was from 8.99 to 28.31?μM. The synthesized compounds possessed higher or equivalent percent retention as compared to piracetam at 1?mg/kg with no other CNS-related activities (locomotor and muscle relaxant, analgesic and anticonvulsant activities). Compound 3-[3-(imidazolo)propoxy]benzenamine has shown significant dose-dependent (1 and 3?mg/kg) memory enhancing activity, while 3-[3-(pyrrolidino)propoxy]benzenamine also showed activity equivalent to reference drug piracetam at 1?mg/kg. Both compounds 3-[3-(pyrrolidino)propoxy]benzenamine and 3-[3-(imidazolo)propoxy]benzenamine were also found to show AChE inhibition with IC50 value of 8.99 and 17.87?μM. The molecular docking, MM-GBSA and molecular dynamics simulation studies were performed in order to establish a relationship between the biological results. RMSD, root-mean-square fluctuations, and interaction patterns of 10a–AChE and Sck–AChE complexes proved that the binding affinity of 10a toward AChE was highly stable with the proposed binding orientations.

Pharmaceutical compositions and methods for use

Patients susceptible to or suffering from conditions and disorders, such as central nervous system disorders, are treated by administering to a patient in need thereof aryloxyalkylamines, including pyridyloxylalkylamines and phenoxyalkylamines. Exemplary compounds include dimethyl(2-(3-pyridyloxy)ethylamine, dimethyl(4-(3-pyridyloxy)butyl)amine, 2-(3-pyridyloxy)ethylamine, 4-(3-pyridyloxy)butylamine, methyl(3-(5-methoxy-3-pyridyloxy)propyl)amine, ethyl(3-(3-pyridyloxy)propyl)amine, methyl(2-(3-pyridyloxy)ethyl)amine, methyl(3-(6-methyl(3-pyridyloxy))propyl)amine, (3-(3-methoxyphenoxy)propyl)methylamine, (3-(5-chloro(3-pyridyloxy))-1-methylpropyl)methylamine, dimethyl(3-(3-pyridyloxy)propyl)amine, 3-(3-pyridyloxy)propylamine, methyl(4-(3-pyridyloxy)butyl)amine, 3-(5-chloro-3-pyridyloxy)propylamine, methyl(3-(5-isopropoxy-3-pyridyloxy)propyl)amine, (3-(5-chloro(3-pyridyloxy))propyl)methylamine, methyl(3-(5-(phenylmethoxy)(3-pyridyloxy))propyl)amine, methyl(3-(2-methyl(3-pyridyloxy))propyl)amine, (methylethyl)(3-(3-pyridyloxy)propyl)amine, benzyl(3-(3-pyridyloxy)propyl)amine, cyclopropyl(3-(3-pyridyloxy)-propyl)amine, methyl(1-methyl-3-(3-pyridyloxy)propyl)amine, methyl(3-(3-nitrophenoxy)propyl)amine, 1-(3-chloropropoxy)-3-nitrobenzene, (3-(3-aminophenoxy)propyl)methylamine, dimethyl(3-(3-(methylamino)-propoxy)phenyl)amine, methyl(3-tricyclo[7.3.1.0]tridec-2-yloxypropyl)amine, (3-benzo[3,4-d]1,3-dioxolan-5-yloxypropyl)methylamine, 3-(4-piperidinyloxy)pyridine and 3-((3S)-3-pyrrolidinyloxy)pyridine.

PHARMACEUTICAL COMPOSITIONS AND METHODS FOR USE

Patients susceptible to or suffering from conditions and disorders, such as central nervous system disorders, are treated by administering to a patient in need thereof aryloxyalkylamines and arylthioalkylamines, including pyridyloxylalkylamines, phenoxyalkylamines, pyridylthiolalkylamines and phenylthioalkylamines. Exemplary compounds include (2-(5-bromo(3-pyridylthio))ethyl)methylamine, (2-(5-bromo(3-pyridylthio))isopropyl)methylamine, (2-(5-bromo(3-pyridylthio))propyl)methylamine, (3-(5-bromo(3-pyridylthio))propyl)methylamine, 3-((3S)-3-pyrrolidinyloxy)pyridine, 3-(4-piperidinyloxy)pyridine, 3-(1-methyl-4-piperidinyloxy)pyridine, (3-benzo[3,4-d]1,3-dioxolan-5-yloxypropyl)methylamine, and methyl(3-tricyclo[7.3.1.0]tridec-2-yloxypropyl)amine.