9-Chloroacridine
[CAS# 1207-69-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate
• Name: 9-Chloroacridine
• Molecular Formula: C₁₃H₈ClN
• Molecular Weight: 213.66
• CAS Registry Number: 1207-69-8
• EC Number: 214-895-2
• SMILES: C1=CC=C2C(=C1)C(=C3C=CC=CC3=N2)Cl

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Melting point: 116-120 ºC (Expl.)
• Index of Refraction: 1.729, Calc.^*
• Boiling Point: 379.4±15.0 ºC (760 mmHg), Calc.^*
• Flash Point: 215.2±6.0 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

9-Chloroacridine is a synthetic organic compound belonging to the class of acridine derivatives, which are widely recognized for their biological and chemical properties. Acridine itself is a heterocyclic compound composed of a fused ring system containing nitrogen, and its derivatives, including 9-chloroacridine, have found application in a variety of fields, such as medicinal chemistry, materials science, and chemical synthesis.

The discovery of 9-chloroacridine is rooted in the exploration of acridine derivatives, which began in the early 20th century. Acridine compounds were initially investigated for their potential use in dyes, as they exhibit distinct fluorescent properties. Over time, the chemical versatility of acridine derivatives led to their broader application, particularly in the fields of pharmaceuticals and chemical synthesis. The chloro substitution at the 9-position of the acridine ring in 9-chloroacridine was found to significantly enhance the compound's biological and chemical reactivity, which paved the way for its use in various applications.

In the field of medicinal chemistry, 9-chloroacridine has attracted attention due to its anticancer and antimicrobial properties. Studies have shown that 9-chloroacridine and its derivatives exhibit activity against a variety of cancer cell lines, suggesting their potential use as chemotherapeutic agents. The compound's ability to intercalate into DNA and inhibit key enzymes involved in DNA replication makes it a promising candidate for the development of new anticancer drugs. The chloro group at the 9-position enhances the compound's lipophilicity, facilitating its passage through cellular membranes and increasing its bioavailability in target tissues. In addition to its anticancer potential, 9-chloroacridine has demonstrated antimicrobial activity, particularly against Gram-positive bacteria, highlighting its potential in the development of new antibiotics.

In chemical synthesis, 9-chloroacridine is used as an intermediate in the production of other acridine derivatives. Its ability to undergo electrophilic substitution reactions, such as halogenation and alkylation, makes it a useful building block for the synthesis of more complex molecules. For instance, 9-chloroacridine can be further functionalized to produce compounds with varying substituents, which may exhibit enhanced biological activity or serve as precursors to other valuable chemicals. This synthetic versatility makes 9-chloroacridine an important reagent in the laboratory and industrial production of acridine-based materials.

9-Chloroacridine has also found applications in the field of materials science, particularly in the development of organic electronic devices. Acridine derivatives, including 9-chloroacridine, exhibit interesting electronic properties, such as the ability to conduct charge and emit light. These properties make them suitable candidates for use in organic light-emitting diodes (OLEDs) and organic solar cells. The presence of the chloro group at the 9-position influences the compound's electronic characteristics, enabling it to perform well as a charge-transport material in these devices. Research into the use of 9-chloroacridine in organic electronics is ongoing, with a focus on improving the efficiency and stability of OLEDs and other organic electronic components.

Despite its promising applications, 9-chloroacridine must be handled with care due to its potential toxicity. Like many acridine derivatives, it can be harmful if ingested or inhaled, and appropriate safety measures should be taken during its synthesis and use. Furthermore, environmental concerns regarding the persistence and biodegradability of acridine derivatives have prompted studies into their environmental impact. Efforts to minimize waste and ensure proper disposal of chemicals like 9-chloroacridine are crucial for reducing their impact on ecosystems.

In conclusion, 9-chloroacridine is a versatile compound with a range of applications in medicinal chemistry, chemical synthesis, and materials science. Its biological activity, particularly as an anticancer and antimicrobial agent, along with its synthetic versatility, make it an important compound in the development of new drugs and chemicals. Ongoing research into its potential applications in organic electronics further expands its utility. As with all chemical compounds, proper handling and disposal are necessary to mitigate any associated risks.