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Acridine
[CAS# 260-94-6]

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Identification
Classification Organic raw materials >> Heterocyclic compound
Name Acridine
Synonyms 10-Azaanthracene; 2,3-Benzoquinoline; 9-Azaanthracene; Benzo[b]quinoline; Dibenzo[b,e]pyridine; NSC 3408
Molecular Structure CAS # 260-94-6, Acridine, 10-Azaanthracene, 2,3-Benzoquinoline, 9-Azaanthracene, Benzo[b]quinoline, Dibenzo[b,e]pyridine, NSC 3408
Molecular Formula C13H9N
Molecular Weight 179.22
CAS Registry Number 260-94-6
EC Number 205-971-6
SMILES C1=CC=C2C(=C1)C=C3C=CC=CC3=N2
Properties
Density 1.2±0.1 g/cm3, Calc.*, 1.016 g/mL (Expl.)
Melting Point 107-110 ºC (Expl.)
Index of Refraction 1.727, Calc.*
Boiling Point 346.7±11.0 ºC (760 mmHg), Calc.*, 346 ºC (Expl.)
Flash Point 153.8±11.9 ºC, Calc.*
* Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Symbols symbol   GHS07 Warning    Details
Hazard Statements H302-H312-H315-H319-H332-H335    Details
Precautionary Statements P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501    Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Acute toxicityAcute Tox.4H302
Eye irritationEye Irrit.2H319
Skin irritationSkin Irrit.2H315
Specific target organ toxicity - single exposureSTOT SE3H335
Chronic hazardous to the aquatic environmentAquatic Chronic1H410
Acute hazardous to the aquatic environmentAquatic Acute1H400
Eye irritationEye Irrit.2AH319
Acute toxicityAcute Tox.4H312
Acute toxicityAcute Tox.4H332
Transport Information UN 2713
SDS Available
up Discovory and Applicatios
Acridine is a heterocyclic organic compound, characterized by a fused ring structure containing nitrogen, specifically consisting of a benzene ring fused with a pyridine ring. Its chemical formula is C9H7N, and it is widely known for its yellow crystalline appearance. Acridine has been of considerable interest to chemists due to its unique structure and its potential applications across a variety of fields, including medicine, materials science, and environmental chemistry.

The discovery of acridine dates back to the early 19th century when it was first isolated from coal tar by the German chemist Carl Gräbe in 1870. Gräbe's work with acridine and other compounds derived from coal tar contributed significantly to the development of organic chemistry during that era. Acridine's chemical structure was later elucidated, confirming it as a nitrogen-containing compound. Over time, it became recognized as a significant member of the class of heterocyclic aromatic compounds, which includes a variety of biologically and industrially important molecules.

One of the major applications of acridine is in the field of medicine. Acridine derivatives, such as acridines and acridine orange, have been utilized as antimicrobial and anticancer agents. Acridine derivatives are known to interact with DNA, inhibiting replication and transcription processes, which makes them effective as chemotherapeutic agents in cancer treatment. Acridine orange, in particular, is widely used in molecular biology and cytogenetics as a fluorescent dye that can stain nucleic acids, allowing researchers to visualize cells and tissues under a microscope. It has applications in fluorescence microscopy and flow cytometry.

Acridine is also employed in the field of materials science. As an organic compound with distinctive electronic properties, acridine and its derivatives have been explored for use in organic light-emitting diodes (OLEDs), organic solar cells, and other electronic devices. Its unique structure allows it to act as a hole-transport material, which is essential for efficient charge injection and transport in electronic devices. Furthermore, acridine-based compounds are being investigated for their potential as optoelectronic materials in the development of more efficient and flexible electronics.

In environmental chemistry, acridine is utilized as an indicator for the presence of aromatic compounds in water and soil. It is used in environmental monitoring to assess contamination levels, as well as to track the biodegradation of toxic substances. The ability of acridine to bind to other organic compounds makes it a useful tool for detecting and measuring environmental pollutants.

In conclusion, acridine is a versatile chemical compound with a broad range of applications in medicine, materials science, and environmental monitoring. Its discovery has paved the way for numerous advancements in drug development, electronic materials, and environmental analysis, solidifying its importance in both scientific research and industrial applications.
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