3-Pyridylacetic acid hydrochloride
[CAS# 6419-36-9]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: 3-Pyridylacetic acid hydrochloride
• Synonyms: 3-Pyridineacetic acid hydrochloride; 2-(3-Pyridinyl)acetic acid hydrochloride
• Molecular Formula: C₇H₇NO₂.HCl
• Molecular Weight: 173.60
• CAS Registry Number: 6419-36-9
• EC Number: 229-148-6
• SMILES: C1=CC(=CN=C1)CC(=O)O.Cl

Properties

• Melting point: 161-163 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety 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
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332

Discovery and Applications

3-Pyridylacetic acid hydrochloride is an important compound in organic chemistry, known for its diverse applications in various fields, including pharmaceuticals, agriculture, and materials science. It is a derivative of pyridine, an aromatic heterocycle containing nitrogen, and acetic acid, a simple carboxylic acid. The unique combination of these two functional groups makes 3-pyridylacetic acid hydrochloride a versatile intermediate in the synthesis of a variety of bioactive molecules and materials.

The synthesis of 3-pyridylacetic acid hydrochloride is typically achieved through the reaction of pyridine derivatives with acetic acid or its derivatives, such as acetyl chloride, in the presence of suitable reagents and solvents. This reaction can be performed under mild conditions, allowing for the efficient formation of the pyridylacetic acid structure. In some cases, further purification is required to isolate the hydrochloride salt, which is more stable and easier to handle than the free acid.

One of the primary applications of 3-pyridylacetic acid hydrochloride is in the pharmaceutical industry, where it serves as a key intermediate in the synthesis of various drug candidates. The compound exhibits a broad spectrum of biological activity, including anti-inflammatory, antimicrobial, and anticancer properties, which have led to its investigation in the development of new therapeutic agents. In particular, the pyridine ring plays a crucial role in interacting with biological targets, while the acetic acid group enhances solubility and bioavailability, making the compound more suitable for use in drug formulations.

In addition to its pharmaceutical applications, 3-pyridylacetic acid hydrochloride is used in agricultural chemistry, particularly as a growth regulator in plants. The compound can influence plant growth and development by modulating various physiological processes. It has been shown to promote rooting, increase resistance to stress, and enhance overall plant health. These properties make 3-pyridylacetic acid hydrochloride a valuable tool in agriculture, especially in the cultivation of crops and the production of horticultural plants.

Furthermore, 3-pyridylacetic acid hydrochloride has found use in materials science. It can be employed in the synthesis of functionalized materials, such as metal-organic frameworks (MOFs) and other coordination compounds. The pyridine group is known for its ability to coordinate with metal ions, and when combined with other functional groups, it can lead to the formation of materials with desirable properties, such as enhanced conductivity or stability.

The compound's potential as a ligand in catalytic processes is also being explored. In particular, 3-pyridylacetic acid hydrochloride can act as a ligand in organometallic chemistry, facilitating various catalytic reactions such as C-C bond formation, oxidation, and reduction. These reactions are essential in the production of fine chemicals and specialty materials.

In conclusion, the discovery and applications of 3-pyridylacetic acid hydrochloride highlight its importance in multiple scientific domains. Whether as a pharmaceutical intermediate, plant growth regulator, or material precursor, the compound continues to play a vital role in advancing research and technology in chemistry, agriculture, and drug development.

References

2009. Microbial Conversion of Vegetable Oil to Rare Unsaturated Fatty Acids and Fatty Alcohols by an Aeromonas hydrophila Isolate. Journal of the American Oil Chemists' Society, 86(8).
DOI: 10.1007/s11746-009-1454-8

2012. Microbial Conversion of Arachidonic Acid to Arachidonyl Alcohol by a New Acinetobacter Species. Journal of the American Oil Chemists' Society, 89(4).
DOI: 10.1007/s11746-012-2057-3