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145688

Sigma-Aldrich

6,9-Dichloro-2-methoxyacridine

97%

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About This Item

Empirical Formula (Hill Notation):
C14H9Cl2NO
CAS Number:
86-38-4
Molecular Weight:
278.13
EC Number:
201-666-7
MDL number:
MFCD00005028
UNSPSC Code:
12352100
PubChem Substance ID:
24848741
NACRES:
NA.22

Assay

97%

form

solid

mp

163-165 °C (lit.)

SMILES string

COc1ccc2nc3cc(Cl)ccc3c(Cl)c2c1

InChI

1S/C14H9Cl2NO/c1-18-9-3-5-12-11(7-9)14(16)10-4-2-8(15)6-13(10)17-12/h2-7H,1H3

InChI key

RYRNQWYNHLLOGX-UHFFFAOYSA-N

General description

6,9-Dichloro-2-methoxyacridine on reaction with quinolizidinylalkylamines yields 4-aminoquinoline and 9-aminoacridine derivatives.

Application

6,9-Dichloro-2-methoxyacridine was used in the synthesis of 9-amino-6-chloro-2-methoxyacridine, N′-(6-Chloro-2-methoxy-acridin-9-yl)-heptylamine and N,N′-bis-(6-chloro-2-methoxy-acridin-9-yl)-hexane-1,6-diamine.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H315,H317,H319,H334,H335

Hazard Classifications

Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Origin of the complex fluorescence emission of 9-amino-6-chloro-2-methoxyacridine. 1. Experiment.
Fan P, et al.
The Journal of Physical Chemistry, 93(18), 6615-6622 (1989)
C Boido Canu et al.
Bollettino chimico farmaceutico, 128(6), 212-215 (1989-06-01)
By reacting three quinolizidinylalkylamines with 4,7-dichloroquinoline and 6,9-dichloro-2-methoxyacridine six derivatives of 4-aminoquinoline and 9-aminoacridine were obtained. These compounds, which are of interest as potential antibacterial, antiprotozoarian, anti-helminthic and antitumoral agents, so far have been tested against lymphocytic leukemia P 388
Lucie Guetzoyan et al.
Bioorganic & medicinal chemistry, 17(23), 8032-8039 (2009-11-03)
A series of acridine derivatives were synthesised and their in vitro antimalarial activity was evaluated against one chloroquine-susceptible strain (3D7) and three chloroquine-resistant strains (W2, Bre1 and FCR3) of Plasmodium falciparum. Structure-activity relationship showed that two positives charges as well
Ana Gomes et al.
ChemMedChem, 9(2), 305-310 (2014-01-30)
Plasmodium falciparum, the causative agent of the most lethal form of malaria, is becoming increasingly resistant to most available drugs. A convenient approach to combat parasite resistance is the development of analogues of classical antimalarial agents, appropriately modified in order

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