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
• Article Data: 38

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

General Description

1,4-Dihydro-1,4-methanonaphthalene, also known as tetralin, is a bicyclic compound with a molecular formula C10H12. It is a colorless liquid with a strong aromatic odor. Tetralin is primarily used as a solvent in various industries, including the production of resins, paints, and coatings. It is also used as a precursor in the synthesis of other chemical compounds, such as pharmaceuticals and fragrances. Tetralin has been found to have potential neuroprotective and antidepressant effects, making it a subject of interest in the field of medicinal chemistry. Additionally, it is known to be a moderate skin irritant and should be handled with proper precaution.

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 
• 23537-80-6 1-bromobenzonorbornadiene 
• 31351-14-1 exo-2-benzonorbornenyl mesylate 
• 75-65-0 tert-butyl alcohol 
• 24573-13-5 5,6,7,8-tetrachlorobenzonorbornadiene 
• 7605-04-1 exo-2-benzonorbornenyl chloride 
• 583-53-9 2,3-dibromobenzene 
• 23537-79-3 2-bromo-1,4-dihydro-1,4-methanonaphthalene 
• 462-80-6 benzyne 
• 7213-64-1 C₁₁H₁₀ 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 

Downstream Products

• 17191-01-4 2-chloro-3-(p-tolylthio)benzonorbornene 
• 79671-58-2 2-Chloro-9-(4-nitro-phenylsulfanyl)-1,2,3,4-tetrahydro-1,4-methano-naphthalene 
• 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 
• 58473-66-8 1,8-Diphenyl-4,5:9,10-dibenzo-11-oxa-4,9-tetracyclo<6.2.1.1^3.60^2,7>dodecadiene 
• 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.

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.

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.