4-(3-Formylphenoxy)benzonitrile: Properties & Lab Use Guide

4-(3-Formylphenoxy)benzonitrile is a bifunctional aromatic compound bearing both an aldehyde and a nitrile group bridged by a diaryl ether linkage, making it a versatile intermediate for organic synthesis and materials research.

Product Name

4-(3-Formylphenoxy)benzonitrile

SKU

B727406

Molecular Formula

C14H9NO2

Functional Groups

Aldehyde (–CHO) and nitrile (–CN) on a diaryl ether scaffold

Appearance

Typically a white to off-white crystalline solid (verify with CoA)

Key Reactivity

Aldehyde group participates in condensation, reductive amination, and Wittig-type reactions; nitrile group undergoes hydrolysis, cycloaddition, and nucleophilic addition

Chemical Identity and Structure

4-(3-Formylphenoxy)benzonitrile (SKU B727406) belongs to the class of diaryl ether aldehydes. Its molecular framework consists of a meta-formyl-substituted phenyl ring connected via an oxygen bridge to a para-cyanophenyl ring. The molecular formula is C₁₄H₉NO₂, with a molecular weight of approximately 223.23 g/mol.

The two electron-withdrawing groups—the aldehyde and the nitrile—confer a relatively electron-deficient aromatic system. The diaryl ether linkage provides conformational flexibility while maintaining conjugation pathways relevant to optical and electronic applications. The meta orientation of the aldehyde on the phenoxy ring is an important regiochemical feature that distinguishes this compound from its ortho and para isomers and influences its reactivity profile.

Storage, Handling, and Safety Guidelines

Storage: Store 4-(3-Formylphenoxy)benzonitrile in a tightly sealed container in a cool, dry, and well-ventilated area, away from heat sources, oxidizing agents, and strong bases. A storage temperature of 2–8 °C or room temperature under inert atmosphere may be appropriate; consult the product Certificate of Analysis (CoA) for confirmed conditions.

Handling: Use appropriate personal protective equipment (PPE), including laboratory coat, chemical-resistant gloves, and safety goggles, when handling this compound. Operations that may generate dust or aerosols should be performed in a fume hood. Avoid inhalation of dust and contact with skin, eyes, or mucous membranes.

Waste Disposal: Dispose of waste material in accordance with local, regional, and national environmental regulations. Do not discharge into drains or the environment. Consult your institution's safety officer for approved disposal pathways for aromatic nitrile-containing compounds.

Note: A full Safety Data Sheet (SDS) should be consulted before use. Specific GHS hazard classifications and first-aid measures are detailed in the SDS available from Aladdin Scientific.

Research Applications and Synthetic Utility

The dual functionality of 4-(3-Formylphenoxy)benzonitrile makes it valuable in multiple areas of chemical research:

• Imine and Schiff Base Formation: The aldehyde group reacts readily with primary amines to form imines (Schiff bases), which are important scaffolds in medicinal chemistry, ligand design, and supramolecular chemistry.
• Heterocycle Synthesis: The aldehyde and nitrile groups can each serve as handles for constructing heterocyclic frameworks such as oxazolines, imidazolines, and triazines, relevant to drug discovery programs.
• Wittig and Knoevenagel Reactions: The aldehyde functionality is compatible with Wittig olefination and Knoevenagel condensation reactions, enabling the introduction of extended conjugated systems for organic electronics and dye applications.
• Polymer and Materials Science: Diaryl ether aldehydes with pendant nitrile groups are of interest as monomers or cross-linking agents in high-performance polymers, liquid crystal materials, and porous organic frameworks.
• Biological Probe Development: Bifunctional aromatic aldehydes serve as pharmacophore building blocks in the synthesis of small-molecule inhibitors and fluorescent probes.

Researchers should optimize reaction conditions—including solvent, temperature, catalyst, and stoichiometry—based on the specific transformation being performed.

Quality, Purity, and Ordering Information

Aladdin Scientific supplies 4-(3-Formylphenoxy)benzonitrile under SKU B727406. The product is intended for research use only and is not suitable for diagnostic, therapeutic, or food applications.

Purity: Specific purity data are provided on the product's Certificate of Analysis (CoA). Researchers requiring high-purity material for sensitive applications such as catalysis, spectroscopy, or biological assays should review the CoA before use and contact Aladdin Scientific technical support if custom purity specifications are required.

Available Quantities: Typical pack sizes and pricing are listed on the product page. Bulk or custom quantities may be arranged through Aladdin Scientific's sales team.

Ordering: Place orders directly through the Aladdin Scientific website or contact your regional distributor. Reference SKU B727406 for accurate procurement.

Frequently asked questions

What are the primary functional groups in 4-(3-Formylphenoxy)benzonitrile and how do they influence reactivity?

The compound contains an aldehyde (–CHO) group on the meta position of one phenyl ring and a nitrile (–CN) group on the para position of the second phenyl ring, connected by a diaryl ether (C–O–C) linkage. The aldehyde enables condensation, reductive amination, and Wittig-type reactions, while the nitrile can undergo hydrolysis to amide or carboxylic acid, cycloaddition to form heterocycles, and nucleophilic addition. Both groups together provide orthogonal reactivity for multi-step synthetic strategies.

How should 4-(3-Formylphenoxy)benzonitrile be stored to maintain stability?

The compound should be stored in a tightly sealed container in a cool, dry, well-ventilated area, away from oxidizing agents, strong bases, and sources of heat or moisture. Refer to the product Certificate of Analysis and Safety Data Sheet for specific confirmed storage temperature and conditions. Storing under an inert atmosphere (nitrogen or argon) may help prevent oxidation or moisture uptake.

Is 4-(3-Formylphenoxy)benzonitrile suitable for use in biological assays?

This compound is supplied for research purposes and can serve as a building block for biologically active molecules, such as small-molecule inhibitors or fluorescent probes, when used in appropriate synthetic workflows. However, it is not validated for direct use in biological assays as a finished reagent. Researchers should assess purity (via the CoA), solubility in relevant buffers or solvents, and any potential cytotoxicity before incorporating it into biological experiments.

What solvents are recommended for dissolving 4-(3-Formylphenoxy)benzonitrile?

Based on the compound's aromatic and relatively electron-deficient structure, common organic solvents such as dimethyl sulfoxide (DMSO), dimethylformamide (DMF), dichloromethane, ethyl acetate, and acetonitrile are expected to provide adequate solubility. Aqueous solubility is anticipated to be low. Solubility should be experimentally confirmed, and the product CoA or technical support from Aladdin Scientific should be consulted for specific solubility data.

References

1. Aladdin Scientific product page: 4-(3-Formylphenoxy)benzonitrile, SKU B727406.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (General aldehyde and nitrile reactivity.)
3. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (Diaryl ether synthesis and bifunctional aromatic compound chemistry.)

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.