4-Amino-2-picoline
[CAS# 18437-58-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Aminopyridine
• Name: 4-Amino-2-picoline
• Synonyms: 4-Amino-2-methylpyridine
• Molecular Formula: C₆H₈N₂
• Molecular Weight: 108.14
• CAS Registry Number: 18437-58-6
• EC Number: 625-782-6
• SMILES: CC1=NC=CC(=C1)N

Properties

• Melting point: 93-97 °C

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H315-H318-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P354+P338-P317-P319-P321-P330-P332+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

4-Amino-2-picoline, a derivative of picoline, was first synthesized in the early 20th century as chemists explored the reactivity of pyridine derivatives. Picoline, a methylpyridine isomer, served as a starting material for various chemical reactions aimed at producing functionalized pyridine derivatives with diverse properties. The synthesis of 4-Amino-2-picoline involves the introduction of an amino group at the 4-position of the picoline ring, yielding a compound with distinct chemical and biological characteristics.

4-Amino-2-picoline serves as a valuable intermediate in the synthesis of pharmaceutical compounds. Its unique structure and reactivity make it an essential building block for the production of various drugs, including antihypertensives, antihistamines, and anti-inflammatory agents. Chemical modifications of the amino group or the pyridine ring enable the creation of drug candidates with improved efficacy, bioavailability, or selectivity.

In the agricultural sector, 4-Amino-2-picoline finds application as a precursor for the synthesis of agrochemicals and pesticides. Pyridine derivatives possess pesticidal properties, and modifications of their structure can enhance their effectiveness against pests and weeds. By incorporating 4-Amino-2-picoline into pesticide formulations, researchers aim to develop products that can protect crops from damage caused by insects, fungi, and other pathogens.

4-Amino-2-picoline is utilized in the formulation of corrosion inhibitors, particularly for metal surfaces exposed to harsh environments. Its chemical properties enable it to form protective layers on metal surfaces, inhibiting corrosion caused by factors such as moisture, oxygen, and chemical pollutants.

As a versatile chemical intermediate, 4-Amino-2-picoline plays a role in the production of dyestuffs and pigments. Its incorporation into dye molecules imparts specific color properties, making it valuable in the textile, printing, and coloring industries.

Beyond its established applications, ongoing research explores new uses for 4-Amino-2-picoline in fields such as materials science, catalysis, and organic synthesis. Scientists investigate its reactivity and potential interactions with other molecules to develop innovative materials, catalysts, and chemical processes.

References

1976 Synthesis of 6- and 8-nitroindolizines. Chemistry of Heterocyclic Compounds, 12(7).
DOI: 10.1007/bf00477009

2011 High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors. Antiviral Research, 92(1).
DOI: 10.1016/j.antiviral.2011.06.006

2022 C-H Amination with Nucleophilic N-H Reagents. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-238-00093