4453-90-1

Basic information

• Product Name: 1,4-DIHYDRO-1,4-METHANONAPHTHALENE
• Synonyms: 1,4-DIHYDRO-1,4-METHANONAPHTHALENE;Benzonorbornadiene;1,4-Methano-1,4-dihydronaphthalene;3,5-[1,2]Benzenocyclopentene;Tricyclo[6.2.1.02,7]undecane-2(7),3,5,9-tetrene;Tricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene;1,4-Methanonaphthalene, 1,4-dihydro-;Nsc120540
• CAS NO: 4453-90-1
• Molecular Formula: C₁₁H₁₀
• Molecular Weight: 142.2
• EINECS: 224-696-2
• Mol File: 4453-90-1.mol

Chemical Properties

• Boiling Point: 220.8 °C at 760 mmHg
• Flash Point: 80.8 °C
• Appearance: /
• Density: 1.108 g/cm³
• Vapor Pressure: 0.164mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,4-DIHYDRO-1,4-METHANONAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DIHYDRO-1,4-METHANONAPHTHALENE(4453-90-1)
• EPA Substance Registry System: 1,4-DIHYDRO-1,4-METHANONAPHTHALENE(4453-90-1)

Safety Data

• Hazardous Substances Data: 4453-90-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Tetralin serves as a precursor in the synthesis of other chemical compounds, particularly in the production of pharmaceuticals and fragrances. Its chemical structure allows for the creation of a wide range of derivatives, making it valuable in the development of new molecules with specific therapeutic or aromatic properties.
Used in Solvent Applications:
In the chemical industry, tetralin is primarily utilized as a solvent for various processes. Its solubility and miscibility with other substances make it suitable for the production of resins, paints, and coatings. It aids in the manufacturing process by dissolving and mixing components, ensuring a uniform final product.
Used in Medicinal Chemistry:
Tetralin has demonstrated potential neuroprotective and antidepressant effects, garnering interest in the field of medicinal chemistry. Researchers are exploring its properties to develop new treatments for neurological disorders and mental health conditions, leveraging its ability to modulate specific biological pathways.
Used in Industrial Processes:
Beyond its applications in chemical synthesis and solvent use, tetralin is also employed in other industrial processes. Its versatility and compatibility with different materials make it a valuable component in the production of various products, contributing to the efficiency and effectiveness of manufacturing operations.

InChI:InChI=1/C11H10/c1-2-4-11-9-6-5-8(7-9)10(11)3-1/h1-6,8-9H,7H2

Upstream product

• 1072-85-1 o-fluorobromobenzene 
• 542-92-7 cyclopenta-1,3-diene 
• 67-56-1 methanol 
• 7213-64-1 5,6-benzotricyclo<3.2.0.0^2,7>hept-5-ene 
• 7605-04-1 exo-2-benzonorbornenyl chloride 
• 7605-05-2 endo-2-benzonorbornenyl chloride 
• 23537-80-6 1-bromobenzonorbornadiene 
• 71925-34-3 2-iodobenzonorbornadiene 
• 917-54-4 methyllithium 
• 558-13-4 carbon tetrabromide 
• 118-92-3 anthranilic acid 
• 7605-04-1 exo-2-benzonorbornyl chloride 
• 31351-14-1 Methanesulfonic acid 1,2,3,4-tetrahydro-1,4-methano-naphthalen-2-yl ester 
• 24573-13-5 5,6,7,8-tetrachlorobenzonorbornadiene 

Downstream Products

• 79671-58-2 2-Chloro-9-(4-nitro-phenylsulfanyl)-1,2,3,4-tetrahydro-1,4-methano-naphthalene 
• 89986-69-6 2-exo-chloro-7-anti-(p-tolylthio)benzonorbornene 
• 17191-01-4 2-chloro-3-(p-tolylthio)benzonorbornene 
• 102203-51-0 1,2,3,4-tetrahydro-2-(phenylethynyl)-3-(phenylsulphonyl)-1,4-methanonaphthalene-(1α,2α,3β,4α) 
• 82521-15-1 1,8-Diphenyl-9,10-(2,2'-biphenylene)-4,5-benzo-4-tetracyclo<6.2.1.1^3,60^2,7>dodecen-11-one 
• 70332-87-5 9-phenyl-6,6a,12,12a-tetrahydro-5H-5,12-cyclo-benzo[e][1,2,4]triazolo[1,2-a]indazole-8,10-dione 
• 55255-94-2 anti-7-benzonorbornenol 
• 7213-64-1 5,6-benzotricyclo<3.2.0.0^2,7>hept-5-ene 
• 26326-70-5 (1R,2R,3S,4S)-1,2,3,4-tetrahydro-1,4-methanonaphthalene-2,3-diol 
• 264-08-4 benzocycloheptatrien 
• 90-12-0 1-Methylnaphthalene 
• 91-57-6 2-Methylnaphthalene 
• 79671-59-3 2-Chloro-9-(2,4-dinitro-phenylsulfanyl)-1,2,3,4-tetrahydro-1,4-methano-naphthalene 
• 79671-56-0 (2S,3S)-2-Chloro-3-(2,4-dinitro-phenylsulfanyl)-1,2,3,4-tetrahydro-1,4-methano-naphthalene 

Relevant articles and documents

Synthesis of (±)-cis-3-aminomethyl-1-tndanylmethanol as a precursor of carbocyclic analogues of nucleosides

Aminoalcohol precursor of carbocyclic analogues of nucleosides (±)-cis-3-aminomethyl-1-indanylmethanol was efficiently synthesized starting from benzonorbornadiene (5) previously prepared by addition of cyclopentadiene to 1-bromo2-fluorobenzene. Copyright

A CoMFA investigation of sigma receptor binding affinity: Reexamination of a spurious sigma ligand

A comparative molecular feld analysis (CoMFA) investigation was conducted on the binding of 64 compounds to σ1 receptors. Although CoMFA accurately predicted the binding affinities of the 64 compounds in the final set (R2 = 0.989), it was unable to predict the high affinity of the previously reported bridged σ ligand SC-50691. SC-50691, and its endo and exo isomers were synthesized and found to bind with much lower affinity than was previously reported.

New carbocyclic nucleosides derived from indan

Seven new carbocyclic nucleosides derived from indan (1a-g) were efficiently prepared from 1,2-indanedimethanol via Mitsunobu reaction with 6-chloroadenine and subsequent introduction of the appropriate substituent.

Synthesis and cytostatic activities of new 6-substituted purinylcarbonucleosides derived from indan

A new series of 6-substituted purinylcarbonucleosides derivatives of indan, 8a-g and 10a-d, was synthesized from (±)-cis-1,3-indandimethanol acetate (5), which was prepared in three steps from benzonorbornadiene. 6-Chloropurine was introduced both by Mitsunobu reaction with 5 and by substitution of the mesylate 6. Suzuki-Miyaura reactions of the protected 6-chloropurine derivative 7 with substituted phenylboronic acids afforded 9a-d (protected purine derivatives with substituted phenyl rings at position 6); deprotection of the latter yielded the new series of purinylcarbonucleoside indan derivatives 10a-d. Treatment of compound 7 with R′H/NaOH afforded a parallel series 8a-g, with alkoxy or amino groups R′ at position 6 instead of substituted phenyl rings.

Iridium-Catalyzed Asymmetric Hydroalkenylation of Norbornene Derivatives

Transition-metal-catalyzed asymmetric hydroalkenylation of alkenes provides an atom-economical method to build molecular complexity from easily available materials. Herein we report an iridium-catalyzed asymmetric hydroalkenylation of unconjugated alkenes with acrylamides and acrylates. The catalytic hydroalkenylation of norbornene derivatives occurred to form products with allylic stereocenters with high chemo-, regio-, and stereoselectivities. DFT calculations revealed that the migratory insertion is irreversible and the enantiodetermination step.

Cobalt(III)-Catalyzed Intermolecular Carboamination of Propiolates and Bicyclic Alkenes via Non-Annulative Redox-Neutral Coupling

A cobalt(III)-catalyzed, redox-neutral, intermolecular carboamination of propiolates and bicyclic alkenes was developed. This non-annulative coupling strategy features atom economy, high regioselectivity, good yields, and functional groups tolerance. Such a carboamination reaction was applied to modified phenols from the corresponding phenols under mild conditions.

Cycloaddition Reactions of Benzonorbornadiene and Homonorbornadiene: New Isoxazoline and Pyridazine Derivatives

Ten new isoxazoline derivatives were synthesized from the reactions of benzonorbornadiene and homonorbornadiene derivatives with nitrile oxides formed from benzaldehyde and 4-substituted benzaldehyde. Two new pyridazine derivatives were also synthesized from the reaction of the homonorbornadiene derivatives with 3,6-di (2-pyridyl)-s-tetrazine. It was seen that all cycloaddition reactions were realized as exo selectivity. Finally, γ-Gauche effect in the isoxazoline derivatives was discussed.

Selective mono-alkylation of N-methoxybenzamides

We report our latest discovery of norbornene derivative modulated highly mono-selective ortho-C-H activation alkylation reactions on arenes bearing simple mono-dentate coordinating groups. The reaction features the use of readily available benzamides and alkyl halides. During the study, we prepared 30 mono-alkylated aryl amides in good yields with good mono-selectivity. We have also demonstrated that structurally rigid alkenes such as norbornene and its derivatives are a good class of ligand and could be used for future direct C-H functionalizations. The utilization of norbornene type ligands for assistance in C-H activation processes has opened a new window for future molecular design using direct C-H functionalization strategies.

KO:TBu-Catalyzed lithiation of PMDTA and the direct functionalization of bridged alkenes under mild conditions

A practical preparation of the reagent PMDTALi using a super base system under mild conditions has been developed. This PMDTALi base has been demonstrated to be a very efficient reagent for the lithiation of bridged alkenes via direct deprotonation. Further reactions with electrophiles and also coupling reactions in the presence of Pd catalysts provide the bridged alkenes with a broad range of functional groups including silyl, alkyl, halogen and aryl substituents. The utilization of this new lithium reagent has brought a new diversity to the choice of lithium reagent for the deprotonation of synthetically challenging systems.

Comparison of alkene hydrogenation in carbon nanoreactors of different diameters: Probing the effects of nanoscale confinement on ruthenium nanoparticle catalysis

The catalytic properties of ruthenium nanoparticles (RuNPs) supported in carbon nanoreactors of different diameters-single walled carbon nanotubes (SWNTs, width of cavity 1.5 nm) and hollow graphitised nanofibers (GNFs, width of cavity 50-70 nm)-were evaluated using exploratory alkene hydrogenation reactions and compared to RuNPs adsorbed on the surface of SWNT or deposited on carbon black in commercially available Ru/C. Supercritical CO2 is shown to be essential to enable efficient transport of reactants to the catalytic RuNPs, particularly for the very narrow RuNP@SWNT nanoreactors. Though the RuNPs in SWNT are observed to be highly active, they simultaneously reduce the accessible volume of very narrow SWNTs by 30-40% resulting in lower overall turnover numbers (TONs). In contrast, RuNPs confined in wider GNFs were completely accessible and demonstrated remarkable activity compared to unconfined RuNPs on the outer surface of SWNTs or carbon black. Control of the nanoscale environment around the catalytic RuNPs significantly enhances the stability of the catalyst and influences the local concentration of reactant molecules in close proximity to the RuNPs, illustrating the comparable importance of confinement to that of metal loading and size of NPs in the catalyst. Interestingly, extreme spatial confinement also appeared not to be the best strategy for controlling the selectivity of hydrogenations in a competitive reaction of norbornene and benzonorbornadiene, with wider RuNP@GNF nanoreactors displaying enhanced selectivity for the hydrogenation of the aromatic group containing alkene (benzonorbornadiene). This is attributed to the presence of nanoscale graphitic step-edges within the GNF making them an attractive alternative to the extremely narrow SWNT nanoreactors for preparative catalysis.