tetraphenylmethane

Tetraphenylmethane is an organic compound consisting of a methane core with four phenyl substituents. It was first synthesized by Moses Gomberg in 1898.

Chemical data

Formula: C25H20
Molecular weight: 320.4 g/mol
IUPAC name: tritylbenzene
SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4
InChIKey: PEQHIRFAKIASBK-UHFFFAOYSA-N
XLogP: 7
Polar surface area: 0 Å²
H-bond donors: 0
H-bond acceptors: 0
Formal charge: 0

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Wikidata facts

Subclass of: aromatic hydrocarbon
Has part: carbon
Mass: 320.156501

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Commons category: Tetraphenylmethane
canonical SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4
chemical formula: C₂₅H₂₀
melting point: 283.0

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Encyclopedic overview

3 sections

Contents

Synthesis
See also
References

Tetraphenylmethane is an organic compound consisting of a methane core with four phenyl substituents. It was first synthesized by Moses Gomberg in 1898.

== Synthesis == Gomberg's classical organic synthesis shown below starts by reacting triphenylmethyl bromide 1 with phenylhydrazine 2 to the hydrazine 3. Oxidation with nitrous acid then produces the azo compound 4 from which on heating above the melting point, nitrogen gas evolves with formation of tetraphenylmethane 5. 500px|Gomberg's tetraphenylmethane synthesis

Excerpted from Wikipedia’s “tetraphenylmethane” article, available under the CC BY-SA 4.0 licence.