3548-09-2

Basic information

• Product Name: 9-AMINO-6-CHLORO-2-METHOXYACRIDINE
• Synonyms: 5-amino-2-chloro-7-methoxyacridine;6-chloro-2-methoxy-9-acridinamin;6-chloro-2-methoxy-9-acridinamine;9-amino-3-chloro-7-methoxy-acridin;9-amino-6-chloro-2-methoxy-acridin;9-AMINO-6-CHLORO-2-METHOXYACRIDINE;ACMA;2-Methoxy-6-chloro-9-aminoacridine
• CAS NO: 3548-09-2
• Molecular Formula: C₁₄H₁₁ClN₂O
• Molecular Weight: 258.7
• Product Categories: API intermediates;Fluorescent;Acridine
• Mol File: 3548-09-2.mol

Chemical Properties

• Melting Point: >250°C
• Boiling Point: 475.1 °C at 760 mmHg
• Flash Point: 241.2 °C
• Appearance: Yellow/Solid
• Density: 1.367 g/cm³
• Vapor Pressure: 3.4E-09mmHg at 25°C
• Refractive Index: 1.734
• Storage Temp.: −20°C
• Solubility: Solubility Insoluble in water; soluble in N, N-dimethylformamide
• PKA: 8.6(at 25℃)
• CAS DataBase Reference: 9-AMINO-6-CHLORO-2-METHOXYACRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 9-AMINO-6-CHLORO-2-METHOXYACRIDINE(3548-09-2)
• EPA Substance Registry System: 9-AMINO-6-CHLORO-2-METHOXYACRIDINE(3548-09-2)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-40
• Safety Statements: 22-26-36
• WGK Germany: 3
• RTECS: AR7330000
• Hazardous Substances Data: 3548-09-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
9-Amino-6-chloro-2-methoxyacridine is used as an intermediate in the synthesis of pharmaceuticals. Its unique chemical structure and properties make it a valuable component in the development of new drugs with potential therapeutic applications.
Used in Dye Industry:
9-Amino-6-chloro-2-methoxyacridine is used as a dye due to its distinct color. Its solubility in organic solvents makes it suitable for various dyeing processes, particularly in the textile and printing industries.
Used in Antimicrobial Applications:
9-Amino-6-chloro-2-methoxyacridine is used as an antimicrobial agent. Its potential to inhibit the growth of microorganisms makes it a valuable tool in the development of new antimicrobial drugs and treatments.
Used in Antitumor Applications:
9-Amino-6-chloro-2-methoxyacridine is used as an antitumor agent. Its potential to inhibit tumor growth and proliferation has been studied for its potential use in cancer treatment, offering a promising avenue for the development of new cancer therapies.
Used in Microscopy:
9-Amino-6-chloro-2-methoxyacridine is used as a staining agent in microscopy. Its ability to bind to specific cellular structures makes it a valuable tool in biological and medical research, aiding in the visualization and analysis of various biological processes.

InChI:InChI=1/C14H11ClN2O/c1-18-9-3-5-12-11(7-9)14(16)10-4-2-8(15)6-13(10)17-12/h2-7H,1H3,(H2,16,17)

Upstream product

• 86-38-4 6,9-dichloro-2-methoxyacridine 
• 98570-61-7 (6-chloro-2-methoxy-acridin-9-yl)-hydrazine 
• 69-05-6 quinacrine dihydrochloride 
• 210584-71-7 6-chloro-2,9-dimethoxyacridine 

Downstream Products

• 83-89-6 quinacrine 

Relevant articles and documents

Microwave-assisted synthesis of 4-quinolylhydrazines followed by nickel boride reduction: a convenient approach to 4-aminoquinolines and derivatives

Nickel(II) chloride/sodium borohydride combination was employed for the reduction of 4-hydrazinoquinoline derivatives to the corresponding anilines. This reductive protocol was efficiently applied for the reductive cleavage of monosubstituted hydrazines. We described herein the microwave-assisted synthesis of 4-hydrazinoquinolines, which furnished a high yielding and rapid two-step procedure for the synthesis, under mild conditions, of 4-aminoquinolines as antimalarial precursors.

Inhibition of Trypanosoma cruzi trypanothione reductase by acridines: Kinetic studies and structure-activity relationships

Series of 9-amino and 9-thioacridines have been synthesized and studied as inhibitors of trypanothione reductase (TR) from Trypanosoma cruzi, the causative agent of Chagas' disease. The compounds are structural analogues of the acridine drug mepacrine (quinacrine), which is a competitive inhibitor of the parasite enzyme, but not of human glutathione reductase, the closest related host enzyme. The 9-aminoacridines yielded apparent K(i) values for competitive inhibition between 5 and 43 μM. The most effective inhibitors were those with the methoxy and chlorine substituents of mepacrine and NH2 or NHCH(CH3)(CH2)4N(Et)2 at C9. Detailed kinetic analyses revealed that in the case of 9- aminoacridines more than one inhibitor molecule can bind to the enzyme. In contrast, the 9-thioacridine derivatives inhibit TR with mixed-type kinetics. The kinetic data are discussed in light of the three-dimensional structure of the TR-mepacrine complex. The conclusion that structurally very similar acridine compounds can give rise to completely different inhibition patterns renders modelling studies and quantitative structure-activity relationships difficult.