Tetrakis(4-nitrophenyl)methane: Properties & Research Uses

Benzene, 1,1',1'',1'''-methanetetrayltetrakis[4-nitro- is a highly symmetric, tetrahedral nitro-functionalized aromatic building block widely used in advanced organic synthesis, coordination chemistry, and the construction of porous organic frameworks.

IUPAC Name

1,1',1'',1'''-methanetetrayltetrakis[4-nitrobenzene]

SKU

B710575

Molecular Formula

C25H16N4O8

Core Architecture

Tetrahedral tetraphenylmethane scaffold with four para-nitro substituents

Functional Group

Nitro (-NO2) groups at all four para positions

Primary Research Use

Precursor for amine-functionalized building blocks and porous organic/metal-organic frameworks

Chemical Structure and Properties

Benzene, 1,1',1'',1'''-methanetetrayltetrakis[4-nitro- (commonly referred to as tetrakis(4-nitrophenyl)methane) is built around a central sp³ carbon atom bonded to four 4-nitrophenyl rings, imparting a near-perfect tetrahedral geometry. This rigid, three-dimensional architecture prevents π-stacking and promotes the formation of porous solid-state assemblies.

The four nitro groups located at the para positions of each phenyl ring provide multiple handles for chemical transformation—most notably catalytic or stoichiometric reduction to the corresponding tetraamine, tetrakis(4-aminophenyl)methane, which is itself a key linker in covalent organic frameworks (COFs) and metal-organic frameworks (MOFs). The compound is typically a pale-yellow to yellow crystalline solid with limited solubility in common protic solvents but moderate solubility in polar aprotic solvents such as DMF and DMSO.

Synthesis and Functionalization

Tetrakis(4-nitrophenyl)methane is typically synthesized via electrophilic aromatic nitration of tetraphenylmethane or through multi-step condensation strategies starting from simpler nitroaromatic precursors. The symmetry of the product facilitates straightforward characterization by ¹H NMR, ¹³C NMR, and mass spectrometry, all of which show the expected equivalence of the four aryl arms.

The nitro groups can be selectively reduced to amines using a variety of conditions, including catalytic hydrogenation (Pd/C, H₂), iron/acetic acid reduction, or tin(II) chloride in acidic media. The resulting tetraamine is a versatile platform for Schiff-base condensation with dialdehydes, enabling the construction of imine-linked porous organic polymers and COFs. Partial reduction or selective mono-functionalization strategies are also reported for accessing unsymmetrical derivatives.

Research Applications

Porous Organic Frameworks and COFs: The tetrahedral geometry of tetrakis(4-nitrophenyl)methane and its tetraamine derivative makes them ideal four-connected nodes for 3D framework construction. Researchers have employed these building blocks to design COFs and porous organic polymers with permanent porosity, high surface areas, and tunable pore environments relevant to gas storage, separation, and heterogeneous catalysis.

Metal-Organic Frameworks (MOFs): After reduction to the tetraamine or conversion to tetracarboxylic acid analogs, the tetraphenylmethane core provides structural rigidity that supports robust MOF topologies. Such frameworks have been explored for CO₂ capture, hydrogen storage, and drug delivery applications.

Organic Electronics and Sensing: The electron-withdrawing nitro groups modulate the HOMO-LUMO gap and can be exploited in fluorescence quenching-based sensing of electron-rich analytes. The compound and its derivatives are also investigated as components of non-linear optical (NLO) materials owing to the push-pull electronic architecture achievable upon asymmetric functionalization.

Supramolecular Chemistry: The 3D shape of tetrakis(4-nitrophenyl)methane supports the formation of inclusion complexes and host-guest assemblies, relevant to studies of molecular recognition.

Handling, Storage, and Safety Considerations

As a nitroaromatic compound, tetrakis(4-nitrophenyl)methane should be handled with standard laboratory precautions. Appropriate personal protective equipment (PPE)—including chemical-resistant gloves, safety glasses, and a laboratory coat—should be worn at all times. Operations that may generate dust or aerosols should be performed in a fume hood.

The compound should be stored in a cool, dry, well-ventilated location away from heat sources, open flames, and incompatible materials such as strong reducing agents. Container should be kept tightly closed when not in use. Consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific for detailed hazard classifications, first-aid measures, disposal guidelines, and transport regulations before use.

Frequently asked questions

What is the molecular formula and molecular weight of tetrakis(4-nitrophenyl)methane?

The molecular formula of tetrakis(4-nitrophenyl)methane is C25H16N4O8. The theoretical molecular weight calculated from this formula is approximately 516.41 g/mol. Researchers should verify the exact value against the certificate of analysis supplied with SKU B710575.

How can the nitro groups in this compound be reduced to amines for COF synthesis?

The four nitro groups can be reduced to amines by catalytic hydrogenation using Pd/C under a hydrogen atmosphere, or by chemical reduction with iron powder in acetic acid, or with tin(II) chloride in concentrated hydrochloric acid. The resulting tetrakis(4-aminophenyl)methane is a widely used four-connected amine node for imine-linked COF synthesis via Schiff-base condensation with aromatic dialdehydes.

What solvents are suitable for dissolving tetrakis(4-nitrophenyl)methane?

Tetrakis(4-nitrophenyl)methane has limited solubility in protic solvents such as water, methanol, and ethanol. It shows moderate solubility in polar aprotic solvents including DMF, DMSO, and NMP, which are commonly used for reactions and film-casting applications. Solubility should be confirmed experimentally for each specific batch and application.

Is tetrakis(4-nitrophenyl)methane available in different purity grades from Aladdin Scientific?

Aladdin Scientific offers tetrakis(4-nitrophenyl)methane under SKU B710575. For specific purity grades, quantities, and pricing, please consult the current product listing on the Aladdin Scientific website or contact the sales team directly. A certificate of analysis is available for each lot.

References

1. Cooper, A. I. Porous Molecular Solids and Liquids. ACS Central Science 2017, 3, 544–553. (General reference on porous organic materials using tetrahedral building blocks.)
2. Ding, S.-Y.; Wang, W. Covalent organic frameworks (COFs): from design to applications. Chemical Society Reviews 2013, 42, 548–568. (Reviews imine-linked COFs incorporating tetrahedral amine nodes.)
3. Aladdin Scientific. Product page: Benzene, 1,1',1'',1'''-methanetetrayltetrakis[4-nitro-, SKU B710575. Retrieved from https://www.aladdin-e.com (date accessed: 2024).

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