3-Cyano-4-fluorobenzaldehyde
[CAS# 218301-22-5]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluorobenzonitrile series
• Name: 3-Cyano-4-fluorobenzaldehyde
• Synonyms: 2-Fluoro-5-formylbenzonitrile
• Molecular Formula: C₈H₄FNO
• Molecular Weight: 149.12
• CAS Registry Number: 218301-22-5
• EC Number: 628-221-3
• SMILES: C1=CC(=C(C=C1C=O)C#N)F

Properties

• Melting point: 80-84 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety 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

Hazard Classification

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

Discovery and Applications

3-Cyano-4-fluorobenzaldehyde is a chemical compound distinguished by its unique combination of functional groups and its applications in various fields. This compound features a benzaldehyde core substituted with both a cyano group and a fluorine atom, providing distinct reactivity and properties.

The discovery of 3-cyano-4-fluorobenzaldehyde stems from research into the development of specialized organic molecules with particular electronic and steric properties. The cyano group (-CN) and fluorine atom (-F) attached to the benzaldehyde ring are known to influence the electronic distribution within the molecule, enhancing its utility in chemical synthesis and material science. The synthesis of 3-cyano-4-fluorobenzaldehyde typically involves the introduction of the cyano group and fluorine atom to the benzaldehyde structure through electrophilic aromatic substitution or similar methods.

In organic synthesis, 3-cyano-4-fluorobenzaldehyde serves as an important intermediate for the preparation of various functionalized compounds. The presence of both the cyano and fluorine groups makes it a valuable building block in the synthesis of pharmaceuticals and agrochemicals. The cyano group, known for its electron-withdrawing effects, and the fluorine atom, which enhances the compound's stability and lipophilicity, together create a versatile reagent for further chemical modifications.

The compound is also used in the development of novel materials and organic electronics. Its electron-deficient nature due to the cyano group makes it suitable for inclusion in electronic materials where controlled electronic properties are required. This includes applications in organic light-emitting diodes (OLEDs) and organic semiconductors, where precise control over electronic interactions is crucial for device performance.

In medicinal chemistry, 3-cyano-4-fluorobenzaldehyde has been explored for its potential role in drug discovery. Its functional groups enable it to interact with biological targets in specific ways, making it a useful scaffold for the development of new drugs. Research into its biological activity and interactions with various targets can lead to the development of novel therapeutic agents.

Overall, 3-cyano-4-fluorobenzaldehyde is a compound with significant utility across several domains, from chemical synthesis to materials science and drug development. Its unique combination of functional groups provides valuable properties for creating innovative solutions in these fields.

References

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2015. Olaparib. *Pharmaceutical Substances*.
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