9-(Bromomethyl)acridine
[CAS# 1556-34-9]

Identification

• Classification: Analytical chemistry >> Liquid chromatography >> HPLC labeling reagent
• Name: 9-(Bromomethyl)acridine
• Synonyms: 9-Bromomethylacridine
• Molecular Formula: C₁₄H₁₀BrN
• Molecular Weight: 272.14
• CAS Registry Number: 1556-34-9
• EC Number: 626-458-7
• SMILES: C1=CC=C2C(=C1)C(=C3C=CC=CC3=N2)CBr

Properties

• Solubility: Insoluble (3.0E^-3 g/L) (25 ºC), Calc.^*
• Density: 1.508±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Melting point: 147-151 ºC^** (Expl.)
• Index of Refraction: 1.739, Calc.^*
• Boiling Point: 420.7±18.0 ºC (760 mmHg), Calc.^*
• Flash Point: 208.2±21.2 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2017 ACD/Labs)

^** Akasaka, Kazuaki; Analytical Letters 1987, V20(10), P1581-94.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Hazard Classification

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

Discovory and Applicatios

9-(Bromomethyl)acridine is an organic compound that consists of an acridine ring structure substituted with a bromomethyl group at the 9-position. It has the chemical formula C10H8BrN and is a derivative of acridine, a well-known nitrogen-containing polycyclic aromatic compound. The structure of 9-(bromomethyl)acridine provides interesting chemical reactivity due to the presence of both a halogen (bromine) and a reactive methyl group, which can undergo various nucleophilic substitution reactions.

The discovery of 9-(bromomethyl)acridine can be traced back to the ongoing exploration of acridine derivatives and their potential applications. Acridine itself was first synthesized in the late 19th century and has since been studied for its diverse biological and chemical properties. The bromomethyl group in 9-(bromomethyl)acridine was introduced as part of synthetic efforts to modify the acridine structure for improved reactivity and to create new compounds with enhanced properties. The bromine atom serves as a leaving group, making this molecule highly useful in chemical synthesis, particularly for reactions that require the introduction of new functional groups.

Synthesis of 9-(bromomethyl)acridine generally involves the bromination of acridine or its derivatives under controlled conditions. Bromine is typically introduced to the molecule through electrophilic aromatic substitution, where the bromine atom attaches to the carbon atom at the 9-position of the acridine ring. The process can be carried out using a variety of bromination agents and solvents, with the reaction conditions adjusted to favor the desired substitution. The use of the bromomethyl group enables further modifications to the compound, including the potential for functionalization at other positions on the acridine ring.

The applications of 9-(bromomethyl)acridine are primarily found in organic synthesis and medicinal chemistry. In organic synthesis, it serves as a versatile intermediate for the creation of more complex molecules. The presence of the bromomethyl group makes it an ideal precursor for nucleophilic substitution reactions, allowing the attachment of various nucleophiles, such as amines, thiols, and alcohols. These modified derivatives of 9-(bromomethyl)acridine can be used to build new molecular scaffolds with diverse functionalities, expanding the range of potential applications in pharmaceuticals, materials science, and catalysis.

One of the key areas where 9-(bromomethyl)acridine has shown promise is in medicinal chemistry. Acridine derivatives, including 9-(bromomethyl)acridine, have been studied for their biological activities, particularly their potential as antitumor agents. The compound has been found to exhibit cytotoxic effects against various cancer cell lines, which makes it a candidate for further investigation as a possible chemotherapy agent. The bromomethyl group can also serve as a useful tool for the development of prodrugs, where it can be used to release an active pharmaceutical compound in a controlled manner. By modifying the bromomethyl group, researchers can optimize the pharmacokinetics and pharmacodynamics of the molecule, enhancing its therapeutic potential.

In addition to its role in drug development, 9-(bromomethyl)acridine has also been explored in the field of materials science. The functionalization of acridine derivatives can lead to the creation of novel materials with unique electronic and optical properties. For example, acridine derivatives are often used in the development of organic light-emitting diodes (OLEDs), and the introduction of the bromomethyl group in 9-(bromomethyl)acridine can provide further opportunities for tuning the properties of these materials. The compound’s ability to form stable complexes with metal ions also opens up the possibility of using it in the synthesis of metal-organic frameworks (MOFs) or as a building block for new types of sensors and catalysts.

Despite its potential, the use of 9-(bromomethyl)acridine is not without challenges. The bromine atom is reactive and can lead to undesirable side reactions, especially in sensitive environments or when used in large-scale synthetic processes. The reactivity of the bromomethyl group must be carefully controlled to avoid undesired by-products. Furthermore, the toxicity and environmental impact of acridine derivatives, including 9-(bromomethyl)acridine, need to be thoroughly assessed before widespread application, particularly in medicinal and industrial settings.

In conclusion, 9-(bromomethyl)acridine is a promising compound with a variety of applications in organic synthesis, medicinal chemistry, and materials science. Its versatile chemical reactivity, particularly the presence of the bromomethyl group, makes it an ideal building block for the creation of complex molecules with a wide range of potential uses. As research into this compound continues, it may lead to the development of new drugs, materials, and technologies that could have significant implications in various fields.

References

Wakako Tsuzuki, Akemi Ue, Akihiko Nagao and Kazuaki Akasaka. Fluorimetric analysis of lipase hydrolysis of intermediate- and long-chain glycerides, Analyst, 2002, 127, 669.