3-(3-Pyridyl)-2-propen-1-ol
[CAS# 69963-46-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound
• Name: 3-(3-Pyridyl)-2-propen-1-ol
• Synonyms: 3-(3-Pyridyl)allyl alcohol
• Molecular Formula: C₈H₉NO
• Molecular Weight: 135.16
• CAS Registry Number: 69963-46-8
• SMILES: C1=CC(=CN=C1)/C=C/CO

Properties

• Solubility: Soluble (81 g/L) (25 ºC), Calc.^*
• Density: 1.115±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Index of Refraction: 1.606, Calc.^*
• Boiling Point: 284.5±20.0 ºC (760 mmHg), Calc.^*
• Flash Point: 125.9±21.8 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H319-H315-H335
• Precautionary Statements: P261-P304+P340-P264-P362-P321-P302+P352-P280-P305+P351+P338-P312-P271

Discovory and Applicatios

3-(3-Pyridyl)-2-propen-1-ol is an organic compound belonging to the class of substituted propenols, characterized by a hydroxyl group on the allylic chain and a pyridine ring attached at the 3-position. It has the molecular formula C8H9NO and consists of a three-carbon propenyl group bearing a terminal hydroxyl function, with the double bond in conjugation with a pyridine ring. This structural arrangement enables it to exhibit both nucleophilic and electrophilic properties, relevant in synthetic chemistry.

The compound has drawn attention in various areas of chemical research due to its structural relation to biologically active molecules, especially those incorporating pyridine rings. Pyridine-containing compounds are widely studied for their relevance in medicinal chemistry, agrochemicals, and material science. The 3-(3-pyridyl) moiety has been identified in several bioactive agents, making it a useful scaffold for further derivatization. The hydroxyallyl functionality contributes to the compound’s reactivity, facilitating its participation in various condensation, oxidation, or esterification reactions.

In synthetic organic chemistry, 3-(3-Pyridyl)-2-propen-1-ol is used as a building block for the preparation of more complex molecules. Its reactive allylic alcohol group allows for modifications via epoxidation, oxidation to aldehydes or acids, or conversion to halides and esters. The compound’s structural motif is often used in the design of heterocyclic compounds, ligands for coordination chemistry, and intermediates in the synthesis of active pharmaceutical ingredients.

Its synthesis typically involves the condensation of 3-pyridinecarboxaldehyde with formaldehyde and a reducing agent or through Grignard-type reactions with suitable precursors. Once synthesized, the product may be purified by distillation or recrystallization, depending on the intended application.

From an application standpoint, the compound and its derivatives have been explored for their potential use in medicinal chemistry. Compounds containing the 3-pyridyl structure have shown promise in the development of drugs with anti-inflammatory, antitumor, or antimicrobial activities. While 3-(3-Pyridyl)-2-propen-1-ol itself is not a registered pharmaceutical, its structural characteristics make it a useful precursor for analogs that may exhibit biological activity.

In research settings, it may also be employed as a probe molecule for studying reaction mechanisms involving nucleophilic substitution or electrophilic addition at the allylic position. It has potential value in the development of new ligands for metal complexation due to the coordinating ability of the pyridine nitrogen, paired with the hydroxyl group’s potential for hydrogen bonding or esterification. These properties are useful in catalysis or molecular recognition systems.

Furthermore, in material sciences and polymer chemistry, derivatives of 3-(3-Pyridyl)-2-propen-1-ol could be explored as functional monomers or additives, particularly where specific electronic or hydrogen bonding properties are required. The conjugated system formed by the pyridine ring and the unsaturated alcohol lends itself to potential optical or electrochemical applications, although such uses would require further validation.

The compound is generally handled under standard laboratory conditions, but like other pyridine derivatives, it should be used in a well-ventilated area and with appropriate personal protective equipment. It is soluble in common organic solvents such as ethanol, dichloromethane, and dimethyl sulfoxide, facilitating its use in both aqueous-organic and fully organic reaction systems.

Overall, 3-(3-Pyridyl)-2-propen-1-ol serves as a versatile intermediate in chemical synthesis and has been incorporated into a wide variety of reaction schemes. Its utility lies in its dual functionality, with both a nucleophilic hydroxyl group and a heteroaromatic ring capable of engaging in π-interactions and coordination chemistry. As such, it continues to be a compound of interest in academic and applied research environments.

References

2018. Fluorination of Allylic and Propargylic Alcohols. Science of Synthesis