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Acridine Orange

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Identification
Molecular formula
C17H19N3
CAS number
494-38-2
IUPAC name
N1-acridin-9-yl-N4,N4-dimethyl-benzene-1,4-diamine
State
State

At room temperature, Acridine Orange is in a solid state. It is often handled as a crystalline powder that requires careful handling due to its staining properties.

Melting point (Celsius)
267.00
Melting point (Kelvin)
540.00
Boiling point (Celsius)
542.00
Boiling point (Kelvin)
815.00
General information
Molecular weight
265.34g/mol
Molar mass
265.3340g/mol
Density
1.2450g/cm3
Appearence

Acridine Orange appears as an orange to reddish-brown powder. It exhibits fluorescence, appearing green in acidic solutions, and red when in basic solutions. This property makes it useful as a nucleic acid-selective fluorescent cationic dye useful for cell cycle determination.

Comment on solubility

Solubility of N1-acridin-9-yl-N4,N4-dimethyl-benzene-1,4-diamine

The solubility of N1-acridin-9-yl-N4,N4-dimethyl-benzene-1,4-diamine in various solvents can greatly influence its application in different chemical environments. Typically, the solubility characteristics of this compound are dictated by several factors:

  • Polarity: Due to the presence of the acridine and dimethyl groups, this compound tends to exhibit moderate polarity. This may indicate a preference for solubility in appropriately polar solvents.
  • Solvent Selection: Commonly used solvents such as DMSO (dimethyl sulfoxide) and ethanol could facilitate dissolution, while non-polar solvents like hexane are less likely to dissolve this compound effectively.
  • Temperature Dependence: The solubility may increase with temperature, allowing for higher concentrations to be achieved in solution at elevated temperatures.

While this compound is not one of the most soluble in water, it is essential to consider that solubility is often expressed in terms of solvent compatibility. As noted in molecular chemistry, “like dissolves like,” suggesting that understanding the functional groups and overall structure can lead to informed predictions about solubility patterns.

Thus, researchers should perform solubility tests in various solvents to determine the most suitable conditions for practical applications.

Interesting facts

Interesting Facts about N1-acridin-9-yl-N4,N4-dimethyl-benzene-1,4-diamine

N1-acridin-9-yl-N4,N4-dimethyl-benzene-1,4-diamine, commonly referred to in scientific literature for its unique structural properties, is a fascinating compound with several interesting aspects:

  • Structure and Functionality: This compound features an acridine moiety, which is notable for its planar structure, making it suitable for intercalating DNA. Such intercalation can effectively influence biological processes.
  • Potential Applications: Due to its ability to intercalate within the DNA structure, researchers are exploring its use in the development of new anticancer therapies. It's believed that compounds like this can help inhibit the replication of cancerous cells.
  • Fluorescent Properties: Many acridine derivatives exhibit fluorescent properties, which can be harnessed in bioimaging techniques. This allows scientists to visualize cellular processes in real-time.
  • Versatile Functional Groups: With the introduction of dimethyl amine groups, this compound may display altered solubility and reactivity, making it suitable for various synthetic pathways and enhancing its biological activity.
  • Historical Context: Acridine derivatives have been known since the late 19th century and have had significant roles in medicinal chemistry, particularly in the development of antimalarial and antibacterial agents.

As researchers continue to delve deeper into the properties and interactions of N1-acridin-9-yl-N4,N4-dimethyl-benzene-1,4-diamine, its potential as a therapeutic agent remains a hot topic of discussion within the scientific community.

Synonyms
9-(p-Dimethylaminoanilino)acridine
ACRIDINE, 9-(p-DIMETHYLAMINOANILINO)-
13365-38-3
T97FI0JKU3
NSC-13002
BRN 0487364
UNII-T97FI0JKU3
DTXSID00158292
N4-9-Acridinyl-N1,N1-dimethyl-1,4-benzenediamine
N-Acridin-9-yl-N',N'-dimethyl-benzene-1,4-diamine
1,4-BENZENEDIAMINE, N4-9-ACRIDINYL-N1,N1-DIMETHYL-
DTXCID6080783
wbernrvmjqykkr-uhfffaoysa-n
WIN 1701
NSC 13002
Acridine, 9-((p-(dimethylamino)phenyl)amino)-
1,4-Benzenediamine, N'-9-acridinyl-N,N-dimethyl-
9-((p-(Dimethylamino)phenyl)amino)acridine
N'-9-Acridinyl-N,N-dimethyl-1,4-benzenediamine
Acridine, 9-[[p-(dimethylamino)phenyl]amino]-
1-N-acridin-9-yl-4-N,4-N-dimethylbenzene-1,4-diamine
CHEMBL34941
N'-(acridin-9-yl)-N,N-dimethylbenzene-1,4-diamine
SCHEMBL3347553
NSC13002
1, N'-9-acridinyl-N,N-dimethyl-
STL088556
AKOS001695772
WLN: T C666 BNJ IMR DN1&1
Acridine, 9-[p-(dimethylamino)anilino]-
[4-(acridin-9-ylamino)phenyl]dimethylamine
DS-006079
ST50991217
SJ000039582
N4-(ACRIDIN-9-YL)-N1,N1-DIMETHYLBENZENE-1,4-DIAMINE