4944-94-9

Usage

Uses

Used in Pest Control Industry:
2,3-dihydro-1H-benz[e]indene is used as a moth repellent for its ability to deter moths from infesting fabrics and garments, thus protecting them from damage.
Used in Chemical Synthesis:
2,3-dihydro-1H-benz[e]indene serves as a precursor in the chemical industry for the production of various other chemicals, including phthalic anhydride, which is an important chemical intermediate for the manufacturing of plastics, resins, and dyes.
Used in Environmental Monitoring:
Due to its presence in cigarette smoke, automobile exhaust, and industrial emissions, 2,3-dihydro-1H-benz[e]indene can be used as an indicator for monitoring the levels of air pollution and the presence of toxic substances in the environment.

InChI:InChI=1/C13H12/c1-2-6-12-10(4-1)8-9-11-5-3-7-13(11)12/h1-2,4,6,8-9H,3,5,7H2

Upstream product

• 6342-87-6 2,3-dihydro-1H-benzindene-1-one 
• 109893-27-8 1,2,3,3a,4,5,9b-hexahydro-cyclopenta[a]naphthalen-2-one semicarbazone 
• 141-52-6 sodium ethanolate 
• 65249-54-9 5-Amino-2,3-dihydro-1H-benzoinden 
• 96508-75-7 6,7,8,9-tetrahydro-1H-cyclopenta[a]naphthalene 
• 72985-38-7 1,4-Dihydronaphthocyclopentene 
• 81396-18-1 3a,9b-Dihydro-3H-cyclopenta[a]naphthalene 
• 7647-47-4 2,3,3a,4,5,9b-Hexahydro-1H-benzoindene 
• 178-83-6 6-oxa-dispiro[4.1.5.2]tetradecane 
• 30146-18-0 tricyclo<7.4.0.0^2,6>tridecane 
• 859070-85-2 9b-methyl-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[a]naphthalene 
• 71-43-2 benzene 
• 875849-08-4 dodecahydro-cyclopenta[a]naphthalene-3a-carboxylic acid ethyl ester 
• 875849-01-7 2,3,4,5-tetrahydro-cyclopenta[a]naphthalene-3a-carboxylic acid ethyl ester 

Downstream Products

• 30146-18-0 tricyclo<7.4.0.0^2,6>tridecane 
• 2088-87-1 naphthalene-1,2-dicarboxylic acid 

Relevant academic research and scientific papers

Platinum-catalyzed aromatization of enediynes via a C-H bond insertion of tethered alkanes

PtCl2 (5 mol %) is an effective catalyst for aromatization of enediynes via a C-H bond insertion of tethered alkanes. The reaction mechanism of this cyclization is proposed to involve platinum-.T-alkyne intermediates. This cyclization works not only for terminal alkynes but also for internal alkynes.

Sequential Suzuki-Miyaura Coupling/Lewis Acid-Catalyzed Cyclization: An Entry to Functionalized Cycloalkane-Fused Naphthalenes

Functionalized angular cycloalkane-fused naphthalenes were prepared using a two-step process involving a Pd-catalyzed Suzuki-Miyaura coupling of aryl pinacol boronates and vinyl triflates followed by a boron trifluoride etherate-catalyzed cycloaromatization.

C-C Bond-Forming and Bond-Breaking Processes from the Reaction of Diesters with Me3SnLi. Synthesis of Complex Bridged Polycycles and Dialkyl Aromatic Compounds

1,2-Aromatic diesters can be transformed into strained bridged polycyclic structures by a two-step procedure consisting of an initial reductive alkylation promoted by alkaline metals, followed by a reaction of the resulting unsaturated diesters with Me3SnLi. We propose that a stanna-Brook rearrangement plays a fundamental role in the formation of the polycyclic organotin acetals obtained. These unusual compounds could be further functionalized by tin-lithium exchange followed by alkylation of the newly formed tertiary carbanion. Alternatively, dialkylated aromatic hydrocarbons have been prepared via a decarbonilation reaction promoted by Me3SnLi. 1,4-Aromatic diesters were reductively dialkylated and then transformed into norbornadienone derivatives by reaction with Me3SnLi. Several stable dibenzonorbornadienones 41 have been prepared in just two steps starting from anthracene 38. The corresponding naphthalene analogues gave 1,4-dialkylnaphthalenes. The synthetic protocols described provide access to structures that are not easily obtained through existing synthetic methodologies.

Synthesis, X-ray crystallography and electrochemistry of three novel copper complexes with imidazole-containing hydantoin and thiohydantoins

The reactions of imidazolemethylene-substituted thiohydantoins with copper(II) chloride yield three kinds of complexes with different copper coordination mode. Binuclear complexes Cu2(L1-H) 2Cl2 (5), Cu2(L2

Rhodium(II)-catalyzed cyclization of bis(N-tosylhydrazone)s: An efficient approach towards polycyclic aromatic compounds

Ahead of the PAC: Polycyclic aromatic compounds (PACs) can be easily accessed by the combination of Suzuki-Miyaura cross-coupling and a [Rh 2(OAc)4]-catalyzed carbene reaction using easily available bis(N-tosylhydrazone)s as intermediates (see scheme; Ts=4-toluenesulfonyl). Copyright

Synthesis of substituted benzene derivatives by homo- and hetero-coupling of 2-bromobenzaldehyde and bromovinylaldehydes followed by McMurry coupling

A convenient synthetic approach to substituted benzene derivatives by modified Ullmann cross-coupling of 2-bromobenzaldehyde and bromovinylaldehydes followed by intramolecular McMurry coupling has been developed.

Ruthenium-catalyzed aromatization of enediynes via highly regioselective nucleophilic additions on a π-alkyne functionality. A useful method for the synthesis of functionalized benzene derivatives

TpRu(PPh3)(CH3CN)2PF6 (10 mol %) catalyst effected the nucleophilic addition of water, alcohols, aniline, acetylacetone, pyrroles, and dimethyl malonate to unfunctionalized enediynes under suitable conditions (100 °C, 12-24 h) and gave functionalized benzene products in good yields. In this novel cyclization, nucleophiles very regioselectively attack the internal C1′ alkyne carbon of enediynes to give benzene derivatives as a single regioisomer. Experiments with methoxy substituents exclude the possible involvement of naphthyl cations as reaction intermediates in the cyclization of (o-ethynylphenyl) alkynes. Deuterium-labeling experiments indicate that the catalytically active species is ruthenium-π-alkyne rather than ruthenium-vinylidene species. This hypothesis is further confirmed by the aromatization of o-(2′-iodoethynyl)phenyl alkynes with alcohols. We propose a nucleophilic addition/insertion mechanism for this nucleophilic aromatization on the basis of a series of experiments.

A facile and efficient synthesis of thieno[2,3-c]furans and furo[3,4-b]indoles via a Pummerer-induced cyclization reaction

The α-thiocarbocation generated from the Pummerer reaction of an o-heteroaroyl-substituted sulfoxide is intercepted by the adjacent keto group to produce an α-thio-substituted heteroaromatic isobenzofuran. In the presence of a suitable dienophile, the reactive o-xylylene undergoes a Diels-Alder cycloaddition followed by an acid-catalyzed ring-opening and aromatization to give heteroaromatic naphthalene derivatives. This one-pot procedure occurs smoothly with electron-deficient dienophiles. The tandem Pummerer cyclization-cycloaddition sequence also occurs intramolecularly using unactivated alkenyl tethers of variable length. With acetylenic dienophiles, the primary cycloadducts undergo in situ ring-opening to produce hydroxynaphthalene derivatives. In the absence of a dienophile, it was possible to prepare 4-(ethylthio)-6-phenylthieno[2,3-c]furan and 1-ethyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole. Various synthetic approaches were used for the preparation of the requisite thiophene- and indole-derived sulfoxide precursors. The facility of the tandem Pummerer-Diels-Alder reaction was very dependent on the experimental conditions used to promote the reaction. The best results were achieved by employing a mixture of acetic anhydride and toluene which contained a catalytic quantity of p-toluenesulfonic acid. The presence of the acid effectively drives the reaction in the desired direction by preventing formation of the acetoxy sulfide, which corresponds to the normal Pummerer product.

Acid-catalyzed rearrangement of cyclobutanols. Syntheses of chrysenes, cyclopentenophenanthrenes, and diarylmethanes

Acid-catalyzed reactions of 8-aryl or 8,8-diarylbicyclooct-2-en-7-ols lead to tetrahydrophenanthrene derivatives.For example 8-(1-naphthyl)-bicyclooct-2-en-7-ols give substituted chrysenes in methanesulphonic acid.In the case of the homologous 7-aryl or 7,7-diarylbicyclohept-2-en-6-ols a novel transformation of diarylmethanes is observed.A mechanism is proposed which accounts for the product distribution observed in these rearrangements.