2-Amino-4-cyanopyridine
[CAS# 42182-27-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Cyanopyridine
• Name: 2-Amino-4-cyanopyridine
• Synonyms: 2-Aminoisonicotinonitrile
• Molecular Formula: C₆H₅N₃
• Molecular Weight: 119.12
• CAS Registry Number: 42182-27-4
• EC Number: 677-660-7
• SMILES: C1=CN=C(C=C1C#N)N

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 148-152 ºC (Expl.)
• Index of Refraction: 1.595, Calc.^*
• Boiling Point: 297.7±20.0 ºC (760 mmHg), Calc.^*
• Flash Point: 133.8±21.8 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Hazard Statements: H301+H311+H331-H301-H311-H315-H319-H331-H335
• Precautionary Statements: P261-P262-P264-P264+P265-P270-P271-P280-P301+P316-P302+P352-P304+P340-P305+P351+P338-P316-P319-P321-P330-P332+P317-P337+P317-P361+P364-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H301
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H331
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

2-Amino-4-cyanopyridine is a chemical compound with the molecular formula C6H5N3. It is a derivative of pyridine, a six-membered ring structure containing one nitrogen atom and five carbon atoms. The compound contains two key functional groups: an amino group (-NH2) at the 2-position and a cyano group (-CN) at the 4-position of the pyridine ring. These functional groups make 2-amino-4-cyanopyridine a versatile molecule in organic synthesis and medicinal chemistry.

The compound was first synthesized and identified as part of efforts to explore modified pyridine derivatives. Pyridine and its derivatives have long been a subject of research due to their diverse chemical reactivity and biological activities. The introduction of functional groups at specific positions on the pyridine ring, such as the amino and cyano groups in 2-amino-4-cyanopyridine, enhances the reactivity and potential utility of these molecules in various chemical processes.

2-Amino-4-cyanopyridine is primarily used as a building block in organic synthesis. The presence of the amino and cyano groups makes it a valuable intermediate in the preparation of more complex molecules. These groups enable the compound to participate in a range of chemical reactions, including nucleophilic substitution and condensation reactions. As a result, 2-amino-4-cyanopyridine is often used in the synthesis of pharmaceuticals, agrochemicals, and other bioactive compounds.

In medicinal chemistry, 2-amino-4-cyanopyridine has been explored for its potential as a precursor in the development of therapeutic agents. The cyano group in particular is known to confer certain biological activities to molecules, and its presence in 2-amino-4-cyanopyridine may contribute to the compound's pharmacological properties. Researchers have investigated its role in the synthesis of various heterocyclic compounds, which may exhibit antimicrobial, anticancer, or other desirable bioactivities. The compound’s versatility as a building block has made it a candidate for drug discovery programs focused on developing new bioactive molecules.

The compound has also found applications in the development of materials. Due to its ability to participate in reactions that lead to the formation of complex molecular structures, 2-amino-4-cyanopyridine has been used in the synthesis of materials with potential applications in electronics, sensors, and other advanced technologies. The functional groups on the pyridine ring offer opportunities for tailoring the properties of materials, making 2-amino-4-cyanopyridine a useful precursor in the design of novel materials with specific properties.

Another area where 2-amino-4-cyanopyridine has been explored is in the field of agricultural chemistry. The cyano group is known to enhance the reactivity of molecules, and it can impart biological activity to compounds, making them potentially useful as pesticides or herbicides. The compound’s ability to serve as an intermediate in the synthesis of agrochemicals has been of interest to researchers working to develop new solutions for crop protection. While research in this area is ongoing, the potential of 2-amino-4-cyanopyridine as a precursor for agrochemical development has been recognized in the literature.

In summary, 2-amino-4-cyanopyridine is a valuable chemical compound with a wide range of applications in organic synthesis, medicinal chemistry, and materials science. Its ability to participate in a variety of chemical reactions, coupled with the presence of the amino and cyano groups, makes it a useful building block for the development of bioactive compounds, pharmaceuticals, and materials with specialized properties. As research continues, the compound’s role in the synthesis of new therapeutic agents, agrochemicals, and advanced materials may expand, further highlighting its utility in both industrial and research settings.

References

2019. Synthesis of azachromones and azachromanones. Chemistry of Heterocyclic Compounds, 55(11).
DOI: 10.1007/s10593-019-02570-x

2019. Synthesis and properties of 2,3-heteroannulated thiochromones - hetero analogs of thioxanthone. Chemistry of Heterocyclic Compounds, 55(2).
DOI: 10.1007/s10593-019-02426-4

2013. In-silico design, synthesis and evaluation of novel DNA-gyrase B inhibitors. Medicinal Chemistry Research, 22(11).
DOI: 10.1007/s00044-013-0518-3