4773-82-4

Usage

Type of compound

Polycyclic aromatic hydrocarbon

Source

Commonly found in coal tar and crude oil

Physical state

Colorless liquid

Odor

Strong, sweet

Uses

Chemical intermediate in production of plastics, dyes, and pharmaceuticals; building block in synthesis of complex organic molecules

Hazard status

Considered a hazardous chemical

Handling precautions

Should be handled with care to avoid exposure

Upstream product

• 18636-55-0 1,1-dimethyl-1H-indene 
• 187737-37-7 propene 
• 2039-88-5 2-bromostyrene 
• 124688-10-4 2,2-dimethyl-1,1-(ethylendithio)indan 

Downstream Products

• 117034-18-1 1-((S)-2-Methyl-1-methylene-indan-2-yl)-4-phenyl-[1,2,4]triazolidine-3,5-dione 
• 70063-93-3 1,2-dimethylindene 
• 2177-48-2 1,3-dimethyl-1H-indene 
• 110346-55-9 2-methyl-1-methylene-2-indenyl hydroperoxide 
• 101640-65-7 1-(2-acetylphenyl)propane-2-one 
• 110327-39-4 C₁₁H₁₂O₄ 
• 91-58-7 2-chloronaphthalene 
• 25097-49-8 2-Benzoyl-1,3-dimethyl-naphthalin 
• 117034-17-0 3b,8a-Dimethyl-2-phenyl-8,8a-dihydro-3bH-2,3a,8b-triaza-cyclopenta[3,4]cyclobuta[1,2-a]indene-1,3-dione 

Relevant academic research and scientific papers

Synthesis of o-Dialkenylbenzenes and Indenes Using Heck and Oxypalladation Reactions

o-Bromostyrenes 2-Br react with various alkenes in the presence of palladium catalysts to give either substituted indene 6 or o-diethenylbenzene derivatives 3, depending on the reaction conditions.Under oxidative conditions the latter can be cyclized to indene derivatives as well. - Keywords: Cross-coupling, Heck; Palladium catalysis; Indanes; Arenes, dialkenyl-N

W(CO)6-Mediated Desulfurdimerization of Dithioketals. Evidence for a Thione Intermediate

Upon treatment with W(CO)6, dithioketals undergo desulfurdimerization to give the corresponding dimeric olefins in good to excellent yields.The mechanism of this the newly discovered reaction has been investigated.Thioketones have been isolated from the reactions of highly crowded dithioketals.The mechanism for the formation of thioketones has been shown to occur via a new type of radical fragmentation process of dithiolane.Thermolysis of 2,2-dimethylindan-1-yl 2-thiophenoxyethyl sulfide in the presence of tert-butyl adamantane-1-peroxycarboxylate (a typical radical initiator) has been studied for comparison.Thioketones react with W(CO)6, giving dimeric olefins and/or undergoing carbene-like insertion reactions.

Photochemistry of Alkylindenes in the Gas Phase

The photochemistry of indene and several alkylindenes has been studied in the gas phase using excitation (254 nm) which populates the S2 state.Reactions observed in the gas phase involve rearrangements different from those observed in solution, as evidenced by the formation of photoproducts explicable in terms of net hydrogen and alkyl migrations.Photodealkylation is also observed at low pressures.In a typical example, gas-phase irradiation of 1-methylindene produces 3-methylindene as the major product, in addition to 2-methylindene, while irradiation in solution leads only to the 2-methyl isomer.The reaction mechanism has been investigated via deuterium-labeling studies, the use of added potential triplet sensitizer and quencher gases, and collisional deactivation by added inert gases.Irradiation of selectively deuterated indenes results in nearly statistical scrambling in the five-membered ring of the indene skeleton, and multiple 1,5 hydrogen or alkyl migrations are proposed.The lack of triplet sensitization, quenching, or enhancement indicates that the photochemistry is derived from a single state.Collisional deactivation results in net quenching of all the photoproducts, with those exclusive to the gas phase quenched at a faster rate than the products observed in solution.Collisional deactivation concomitantly results in an enhancement in fluorescence emission, with little emission observed upon excitation into S2 in the absence of a quencher gas.A reaction scheme is proposed which involves the generation of photoproducts from S2 and S1vib.