Tetrakis(4-cyanophenyl)methane: Properties & Lab Use FAQs

Tetrakis(4-cyanophenyl)methane is a tetrahedral, C3v-symmetric organic molecule bearing four para-cyanophenyl arms that make it a versatile building block for porous organic frameworks, coordination polymers, and advanced functional materials research.

Chemical Name

Tetrakis(4-cyanophenyl)methane

SKU / Catalog Number

B299809

Molecular Formula

C29H16N4

Molecular Weight

432.46 g/mol

Core Geometry

Tetrahedral carbon center with four para-cyanophenyl substituents

Key Functional Group

Nitrile (–C≡N), four per molecule

What Is Tetrakis(4-cyanophenyl)methane and Why Is It Used in Research?

Tetrakis(4-cyanophenyl)methane (catalog SKU B299809) is an organic compound consisting of a central quaternary carbon atom bonded to four 4-cyanophenyl (para-cyanophenyl) groups. The result is a rigid, three-dimensional, tetrahedral scaffold that presents four nitrile (–C≡N) groups pointing outward in a near-tetrahedral arrangement.

Because of this geometry, the molecule is widely studied as a tetrafunctional building block in the assembly of porous organic cages, covalent organic frameworks (COFs), metal–organic frameworks (MOFs), and coordination polymers. The nitrile groups can act as nitrogen-donor ligands toward metal ions or can be further transformed—for example, by hydrolysis to carboxylic acids or by cycloaddition chemistry—broadening its synthetic utility. Researchers also employ it in studies of molecular self-assembly, host–guest chemistry, and as a precursor to functional porous carbons after pyrolysis.

Physical and Chemical Properties Relevant to Laboratory Handling

Appearance: Tetrakis(4-cyanophenyl)methane is typically obtained as a white to off-white crystalline solid at room temperature.

Molecular weight: 432.46 g/mol (molecular formula C₂₉H₁₆N₄).

Solubility: The compound is sparingly soluble in common protic solvents such as water and ethanol. It shows better solubility in polar aprotic solvents such as dimethyl sulfoxide (DMSO), dimethylformamide (DMF), and N-methyl-2-pyrrolidone (NMP). Chlorinated solvents (e.g., dichloromethane, chloroform) and tetrahydrofuran (THF) may also dissolve small quantities with heating. Always perform a small-scale solubility test before scaling up.

Thermal stability: As an all-aromatic nitrile compound, it is expected to be thermally robust; however, specific decomposition temperatures should be confirmed from supplier safety documentation or original literature before high-temperature applications.

Storage: Store in a cool, dry location away from heat sources and moisture, in a tightly sealed container. Standard laboratory ambient storage (room temperature, dark) is generally appropriate pending review of the specific SDS supplied with SKU B299809.

Key Applications in Materials and Chemical Research

Porous Organic Frameworks and Cages: The tetrahedral symmetry of Tetrakis(4-cyanophenyl)methane makes it a privileged node for constructing three-dimensional porous networks. When combined with suitable linkers under solvothermal or solution-phase conditions, it can yield materials with permanent porosity useful for gas adsorption, separation, and storage studies.

Metal–Organic Frameworks (MOFs) and Coordination Polymers: The four nitrile nitrogens function as soft Lewis-base donors capable of coordinating to transition metals (e.g., Cu, Ag, Cd, Co). This makes the molecule a candidate four-connected ligand in MOF synthesis, where the resulting network topology is strongly influenced by the tetrahedral geometry of the carbon core.

Covalent Organic Frameworks (COFs): After conversion of the nitrile groups (e.g., to amines via reduction, or to carboxylic acids via hydrolysis), the resulting tetrafunctional monomer can participate in imine, amide, or other condensation reactions to form COFs with defined pore structures.

Functional Carbon Materials: Pyrolysis of nitrile-rich organic precursors is a well-established route to nitrogen-doped porous carbons applicable in electrocatalysis, energy storage, and sensing. Tetrakis(4-cyanophenyl)methane is structurally attractive for this purpose due to its high nitrogen content and 3D architecture.

Molecular Self-Assembly and Supramolecular Chemistry: The rigid tetrahedral scaffold supports the construction of defined supramolecular architectures including capsules, prisms, and other polyhedral assemblies when combined with appropriate metal or organic partners.

Safety, Handling and Regulatory Considerations

As with all laboratory reagents, standard good laboratory practice (GLP) should be followed when handling Tetrakis(4-cyanophenyl)methane. While this compound does not carry the acute toxicity profile of free hydrogen cyanide, the presence of four nitrile groups means that appropriate precautions are warranted:

• Personal Protective Equipment (PPE): Wear nitrile gloves, safety glasses or goggles, and a lab coat. If generating dust during weighing, use a fume hood or respiratory protection.
• Ventilation: Handle in a well-ventilated area or fume hood, particularly when dissolving in heated solvent systems.
• Disposal: Dispose of waste in accordance with local institutional and governmental regulations for nitrile-containing organic compounds. Do not pour down the drain without authorization.
• SDS: Always consult the Safety Data Sheet provided with SKU B299809 from Aladdin Scientific before use. The SDS supersedes any general guidance provided here with respect to hazard classification, first-aid measures, and transport regulations.

Note: Specific GHS hazard classifications, signal words, and R/S or H/P statements for this exact compound should be verified from the current SDS, as these may be updated.

Ordering, Specifications and Quality at Aladdin Scientific

Tetrakis(4-cyanophenyl)methane is available from Aladdin Scientific under catalog number B299809. When placing an order or evaluating this product, consider the following:

• Purity: Confirm the purity grade and analytical method (e.g., HPLC, GC, NMR) from the current product page or Certificate of Analysis (CoA). Research-grade reagents are typically offered at ≥95% or ≥98% purity; verify the specific lot purity on the CoA accompanying your shipment.
• Available pack sizes: Multiple quantities may be available to suit initial exploratory work through larger-scale synthesis needs. Check the product listing at Aladdin Scientific for current pack-size options and pricing.
• Lead time and shipping: Standard domestic and international shipping options apply. For time-sensitive projects, contact Aladdin Scientific customer service to confirm stock availability and estimated delivery.
• Returns and quality issues: If the product does not meet specification, contact Aladdin Scientific customer service with your order number and CoA details. Refer to the current Returns and Refunds policy on the Aladdin website.
• Bulk and custom inquiries: For quantities beyond standard catalog offerings, reach out to the Aladdin Scientific sales team to discuss custom synthesis, bulk pricing, or alternative packaging.

Frequently asked questions

What is the molecular formula and molecular weight of Tetrakis(4-cyanophenyl)methane?

The molecular formula of Tetrakis(4-cyanophenyl)methane is C29H16N4, giving a molecular weight of approximately 432.46 g/mol. The structure consists of a central quaternary carbon bonded to four 4-cyanophenyl rings, each bearing a terminal nitrile group.

What solvents are suitable for dissolving Tetrakis(4-cyanophenyl)methane?

Tetrakis(4-cyanophenyl)methane is sparingly soluble in water and short-chain alcohols. Polar aprotic solvents such as DMF, DMSO, and NMP are generally the best choices for achieving reasonable concentrations. Chlorinated solvents (DCM, chloroform) and THF may dissolve limited amounts, particularly when warmed. A preliminary solubility screen at small scale is recommended before committing to large-scale reactions.

Why is the tetrahedral geometry of Tetrakis(4-cyanophenyl)methane important for framework synthesis?

The tetrahedral geometry enforces a three-dimensional connectivity pattern when the molecule acts as a four-connected node in a network. This directionality promotes the formation of 3D rather than 2D structures, is critical for generating permanent porosity, and determines the topology of the resulting framework. The rigid aromatic arms also reduce conformational flexibility, yielding more predictable and reproducible network architectures.

Can the nitrile groups in Tetrakis(4-cyanophenyl)methane be chemically transformed for further synthesis?

Yes. The four nitrile groups are chemically versatile handles. They can be reduced to primary amines (–CH2NH2) using reagents such as LiAlH4 or via catalytic hydrogenation, enabling subsequent imine or amide condensation chemistry. Acidic or basic hydrolysis converts nitriles to carboxylic acids, opening pathways to carboxylate-based MOF linkers. Nitrile cycloaddition reactions (e.g., with azides to give tetrazoles) are also well documented in the broader nitrile chemistry literature.

Is Tetrakis(4-cyanophenyl)methane hazardous, and what precautions should I take?

While it is not as acutely toxic as free cyanide salts or HCN, Tetrakis(4-cyanophenyl)methane contains four nitrile groups and should be treated with appropriate caution. Use nitrile gloves, safety glasses, and handle in a fume hood, especially when generating dust or working with warm solutions. Always consult the Safety Data Sheet (SDS) provided with SKU B299809 for authoritative hazard classification, first-aid, and disposal information specific to this product.

How should I store Tetrakis(4-cyanophenyl)methane to maintain its quality?

Store Tetrakis(4-cyanophenyl)methane in a tightly sealed container in a cool, dry, and dark location away from heat sources and moisture. Under these conditions, the compound, being a stable all-aromatic solid, is expected to have an acceptable shelf life. Confirm specific storage temperature recommendations and shelf-life data from the SDS and Certificate of Analysis accompanying SKU B299809.

References

1. Aladdin Scientific product listing for Tetrakis(4-cyanophenyl)methane, SKU B299809.
2. General textbook reference: March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Nitrile chemistry and transformations.
3. General reference on tetrahedral building blocks in porous framework synthesis — specific journal articles to be identified and verified by technical reviewer.

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