4-Cyanobenzaldehyde
[CAS# 105-07-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Cyanide/nitrile
• Name: 4-Cyanobenzaldehyde
• Synonyms: 4-Formylbenzonitrile
• Molecular Formula: C₈H₅NO
• Molecular Weight: 131.13
• CAS Registry Number: 105-07-7
• EC Number: 203-267-3
• SMILES: C1=CC(=CC=C1C=O)C#N

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 100-102 °C (Expl.)
• Index of Refraction: 1.552, Calc.^*
• Boiling Point: 262.3±0.0 °C (760 mmHg), Calc.^*, 133 °C (12 mmHg) (Expl.)
• Flash Point: 124.2±22.6 °C, Calc.^*

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

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

Discovery and Applications

4-Cyanobenzaldehyde is an aromatic compound featuring a cyano group (-CN) and an aldehyde group (-CHO) attached to a benzene ring. This dual functionality makes it a versatile intermediate in organic synthesis and industrial applications. The compound has attracted significant interest in fields ranging from material science to pharmaceutical development due to its reactivity and structural features.

The synthesis of 4-cyanobenzaldehyde can be achieved through various methods, with a common approach involving the direct cyanation of benzaldehyde derivatives or the partial oxidation of 4-cyanotoluene. Catalytic processes often employ metal catalysts such as palladium or copper to ensure high yield and selectivity. Advanced green chemistry techniques have also been developed to minimize environmental impact during production.

In pharmaceutical research, 4-cyanobenzaldehyde serves as a key intermediate for synthesizing a wide range of bioactive compounds. Its aldehyde group allows for Schiff base formation and other nucleophilic addition reactions, enabling the creation of derivatives with diverse biological activities. These derivatives have been explored for their potential as anti-inflammatory, antimicrobial, and anticancer agents. The cyano group adds an electron-withdrawing effect that modulates the physicochemical properties of resulting molecules, such as solubility and stability.

In material science, 4-cyanobenzaldehyde is employed in the preparation of polymers and liquid crystalline materials. Its rigid aromatic structure and polar functional groups contribute to the alignment properties and thermal stability required for advanced optical and electronic applications. Additionally, it is used in the synthesis of dyes and pigments, where its reactive functional groups enable binding to various substrates.

The compound’s role in chemical research extends to its use as a building block for heterocyclic compounds. Cyclization reactions involving 4-cyanobenzaldehyde lead to the formation of nitrogen-containing rings, such as quinolines and isoquinolines, which are valuable in both medicinal and industrial chemistry.

Future advancements aim to improve the synthesis and functionalization of 4-cyanobenzaldehyde, with a focus on developing environmentally friendly methods and exploring its potential in novel applications, such as nanotechnology and renewable energy systems.

References

2022. Iridium-Catalyzed Multicomponent Reaction. Science of Synthesis, SD-115-00931.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-115-00931

2023. A facile and efficient one-pot procedure for the synthesis of 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitriles in PEG-400 and glycerol. Research on Chemical Intermediates, 49, 5188.
DOI: 10.1007/s11164-023-05188-z

2023. Synthesis, in-vitro and in-silico antibacterial and computational studies of selected thiosemicarbazone-benzaldehyde derivatives as potential antibiotics. SN Applied Sciences, 5(7), 5429.
DOI: 10.1007/s42452-023-05429-1