1587-22-0

Usage

Chemical structure

Two benzene rings connected by a double bond

Functionality

Optical brighteners and fluorescent dyes

Absorption and emission of light

Yes

Industrial applications

Production of pigments, resins, and pharmaceuticals

Organic synthesis

Used as a building block in the production of various products

Potential medical uses

Anti-cancer and anti-fungal properties

Molecular weight

Approximately 180.25 g/mol

Appearance

Colorless to pale yellow solid or liquid

Solubility

Soluble in organic solvents like ethanol, acetone, and benzene

Melting point

Around 74-77°C (165.2-170.6°F)

Boiling point

Around 304°C (577.2°F)

Density

Approximately 1.02 g/cm3

Hazardous properties

May be harmful if swallowed, inhaled, or absorbed through the skin

Safety measures

Use appropriate personal protective equipment (PPE) and handle in a well-ventilated area

Storage

Store in a cool, dry, and well-ventilated area, away from heat and open flames

Environmental impact

May be toxic to aquatic life and should be handled with care to prevent environmental contamination

Regulatory status

Subject to various regulations depending on the region and intended use

Synonyms

1,1'-(1,2-Ethenediyl)bisbenzene, trans-Stilbene, E-Stilbene, and (E)-1,2-Diphenylethylene

Upstream product

• 183313-79-3 2-(1-diazoethyl)-1,1'-biphenyl 
• 27643-12-5 4-benzyl-2-phenyl-Δ²-1,3,4-oxadiazolin-5-one 

Downstream Products

• 85-01-8 phenanthrene 
• 776-35-2 9,10-dihydrophenanthrene 
• 1235283-88-1 N-(2-(2-phenylstyryl)-5-methylphenyl)acetamide 
• 745809-62-5 9-(4-methylbenzyl)-9H-fluorene 
• 1016652-87-1 9-(2,4,6-trimethylbenzyl)-9H-fluorene 

Relevant academic research and scientific papers

Intramolecular reactivity of arylcarbenes: Biphenyl-2-ylcarbenes

Biphenyl-2-ylcarbenes, 2-ArC6H4CR, were generated photolytically and thermally from diazo precursors. Cyclization, leading to fluorenes, competes with capture of the carbenes by methanol but proceeds faster than intramolecular hydrogen shifts (with R = Me) and intermodular C - H insertion reactions (with R = H in cyclohexane). By comparison of product ratios with kinetic data for related carbenes from the literature, the cyclization rate is estimated as ca 1011 s-1. The intramolecular reactivity of biphenyl-2-ylcarbenes is not significantly attenuated by variation of R (R = H, Me, Ph). Very minor effects of triplet sensitization and methanol quenching indicate that fluorenes arise from spin-equilibrated biphenyl-2-ylcarbenes, presumably from the singlet state. When Ar = mesityl, the carbene predominantly inserts into C - H bonds of the 2′-methyl groups, giving rise to a dihydrophenanthrene. Formation of a fluorene derivative, by formal insertion into C - C bonds, occurs as a minor process. This unprecedented reaction points to intervention of an o-xylylene in which the methyl group migrates. Laser flash photolysis (LFP) of 2-PhC6H4CN2Ph generates a transient absorption which is due to the T0→Tn transition of 9-phenylfluorene rather than to the presumed o-xylylene. On LFP of 2-ArC6H4CN2Ph in trifluoroethanol-acetonitrile, protonation of the carbenes gives rise to carbocations, 2-ArC6H4CH+Ph. The transient absorption spectra of these cations are strongly influenced by twisting about the Ar - Ar bond (Ar = Ph 4.

Evidence for a 1,3-Sigmatropic Rearrangement of a Nitrile N-Benzylimide to a C-Benzyl-substituted Diazoalkane

The flash vacuum pyrolysis of N-benzyl-2-phenyl-1,3,4-oxadiazolin-5-one generates a nitrile N-imide which rearranges to a diazoalkane via a 1,3-sigmatropic benzyl shift.