1,4-Dihydro-1,4-methanonaphthalene

Base Information

• Chemical Name: 1,4-Dihydro-1,4-methanonaphthalene
• CAS No.: 4453-90-1
• Molecular Formula: C11H10
• Molecular Weight: 142.2
• Hs Code.: 2902909090
• European Community (EC) Number: 224-696-2
• NSC Number: 120540
• DSSTox Substance ID: DTXSID20873253
• Nikkaji Number: J110.592B
• Mol file: 4453-90-1.mol

Synonyms:1,4-Dihydro-1,4-methanonaphthalene;4453-90-1;Benzonorbornadiene;1,4-Methanonaphthalene, 1,4-dihydro-;tricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene;EINECS 224-696-2;Benzonorbornadien;NSC120540;1, 1,4-dihydro-;IEGYXSAHRKJELM-UHFFFAOYSA-;DTXSID20873253;CS-B0002;AKOS016004396;NSC 120540;NSC-120540;AC-26379;CS-13473;D5848;FT-0695339;J-503993;tricyclo[6.2.1.0?,?]undeca-2(7),3,5,9-tetraene;56842-50-3

Chemical Property of 1,4-Dihydro-1,4-methanonaphthalene

Chemical Property:

• Vapor Pressure: 0.164mmHg at 25°C
• Refractive Index: 1.624
• Boiling Point: 220.8 °C at 760 mmHg
• Flash Point: 80.8 °C
• PSA: 0.00000
• Density: 1.108 g/cm³
• LogP: 2.82730
• Storage Temp.: 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 142.078250319
• Heavy Atom Count: 11
• Complexity: 172

Purity/Quality:

99% ^*data from raw suppliers

1,4-Dihydro-1,4-methanonaphthalene 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C=CC1C3=CC=CC=C23

Technology Process of 1,4-Dihydro-1,4-methanonaphthalene

There total 40 articles about 1,4-Dihydro-1,4-methanonaphthalene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1-Bromo-2-iodobenzene (583-55-1) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → 1,4-dihydro-1,4-methanonaphthalene (4453-90-1)

Guidance literature:

With lanthanum; iodine; In tetrahydrofuran; at 25 ℃; for 4h;

DOI:10.1016/S0040-4039(02)00958-9

Reference yield: 100.0%

1,4,5,8-Tetrahydro-1,4-methano-naphthalene (143726-64-1) → 1,4-dihydro-1,4-methanonaphthalene (4453-90-1)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In chloroform; for 48h; Ambient temperature;

DOI:10.1016/0040-4020(96)00877-0

Reference yield: 99.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) → 1,4-dihydro-1,4-methanonaphthalene (4453-90-1)

Guidance literature:

With cesium fluoride; In acetonitrile; at 60 ℃; for 16h; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.9b02016

upstream raw materials:

o-fluorobromobenzene

cyclopenta-1,3-diene

methanol

5,6-benzotricyclo<3.2.0.0^2,7>hept-5-ene

Downstream raw materials:

1,2,3,4-tetrahydro-2-(phenylethynyl)-3-(phenylsulphonyl)-1,4-methanonaphthalene-(1α,2α,3β,4α)

1,8-Diphenyl-9,10-(2,2'-biphenylene)-4,5-benzo-4-tetracyclo<6.2.1.1^3,60^2,7>dodecen-11-one

9-phenyl-6,6a,12,12a-tetrahydro-5H-5,12-cyclo-benzo[e][1,2,4]triazolo[1,2-a]indazole-8,10-dione

anti-7-benzonorbornenol

Refernces

• 1、 Eisch,Burlinson. "". . p. 753,759. Retrieved 1976.
• 2、 Adam,W.,Delucchi,O.. "-". . p. 2109. Retrieved 1980.
• 3、 Abad,Alvarez,Fernandez,Garcia-Mera,Rodriguez-Borges. "New carbocyclic nucleosides derived from indan". . p. 1127 - 1128. Retrieved 2001.
• 4、 Wilt,J.W. et al.. "". . p. 893 - 901. Retrieved 1967.
• 5、 Zhu, Yuelu,Chen, Feng,Zhao, Xinyang,Yan, Dingyuan,Yong, Wanxiong,Zhao, Jing. "Cobalt(III)-Catalyzed Intermolecular Carboamination of Propiolates and Bicyclic Alkenes via Non-Annulative Redox-Neutral Coupling". supporting information. p. 5884 - 5888. Retrieved 2019/08/20.
• 6、 Aygün, Mehtap,Stoppiello, Craig T.,Lebedeva, Maria A.,Smith, Emily F.,Gimenez-Lopez, Maria Del Carmen,Khlobystov, Andrei N.,Chamberlain, Thomas W.. "Comparison of alkene hydrogenation in carbon nanoreactors of different diameters: Probing the effects of nanoscale confinement on ruthenium nanoparticle catalysis". . p. 21467 - 21477. Retrieved 2017/10/23.