Bibenzyl

Bibenzyl, also called 1,2-diphenylethane, is an organic compound consisting of two phenyl rings linked by an ethane bridge. Its chemical formula is C14H14. The molecule is nonpolar and flexible, with rotation around the central C–C bond; the two rings are not conjugated, unlike stilbenes.

Bibenzyl occurs as a minor natural product in some plants and resins and serves as the core skeleton for a range of diarylethane and polyphenolic natural products. It is also used as a building block in organic synthesis to access substituted bibenzyls and related stilbenoid compounds.

In terms of preparation, bibenzyl can be prepared by hydrogenation of stilbene, which reduces the carbon–carbon double bond to a single bond. It can also be formed by reductive coupling of benzyl halides in a Wurtz-type reaction, assembling the two benzyl fragments onto a single ethane chain.

Physically, bibenzyl is typically a colorless solid that is sparingly soluble in water but dissolves in a variety of organic solvents. In research and industry, derivatives of bibenzyl are utilized as scaffolds for the synthesis of more complex polyphenolic compounds and as intermediates in the preparation of stilbenoid analogs. Some bibenzyl derivatives have been investigated for biological activity, including antioxidant and antimicrobial properties, though they are not widely used as commercial drugs.