5-Iodo-1,4-dihydro-1,4-methano-naphthalene

Base Information

• Chemical Name: 5-Iodo-1,4-dihydro-1,4-methano-naphthalene
• CAS No.: 63608-69-5
• Molecular Formula: C₁₁H₉I
• Molecular Weight: 268.097
• DSSTox Substance ID: DTXSID80979821
• Mol file: 63608-69-5.mol

Synonyms:63608-69-5;1,4-Methanonaphthalene, 1,4-dihydro-5-iodo-;1,4-Methanonaphthalene,1,4-dihydro-5-iodo-;5-Iodo-1,4-dihydro-1,4-methano-naphthalene;SCHEMBL4689201;DTXSID80979821;5-iodo-1,4-dihydro-1,4-methanonaphthalene

Chemical Property of 5-Iodo-1,4-dihydro-1,4-methano-naphthalene

Chemical Property:

• Vapor Pressure: 0.0105mmHg at 25°C
• Boiling Point: 271.8°C at 760 mmHg
• Flash Point: 120.8°C
• Density: 1.782g/cm³
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 267.97490
• Heavy Atom Count: 12
• Complexity: 221

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C=CC1C3=C2C=CC=C3I

Technology Process of 5-Iodo-1,4-dihydro-1,4-methano-naphthalene

There total 3 articles about 5-Iodo-1,4-dihydro-1,4-methano-naphthalene 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: 30.0%

2,6-difluoroiodobenzene (13697-89-7) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → 5-fluoro-1,4-dihydro-1,4-methano-naphthalene (61346-81-4) + 5-iodobenzonorbornadiene (63608-69-5)

Guidance literature:

With ethylmagnesium bromide; magnesium; In tetrahydrofuran; for 1h; Heating;

DOI:10.1021/ol049655l

Reference yield:

1,3-Difluorobenzene (372-18-9) → 5-iodobenzonorbornadiene (63608-69-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 1.25 h / -78 °C

1.2: 55 percent / I₂ / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 30 percent / Mg; EtMgBr / tetrahydrofuran / 1 h / Heating

With n-butyllithium; ethylmagnesium bromide; magnesium; In tetrahydrofuran; hexane; 2.1: Diels-Alder cycloaddition;

DOI:10.1021/ol049655l

Reference yield:

1-iodo-2,3-difluorobenzene (64248-57-3) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → 5-fluoro-1,4-dihydro-1,4-methano-naphthalene (61346-81-4) + 5-iodobenzonorbornadiene (63608-69-5)

Guidance literature:

With magnesium; In tetrahydrofuran;

DOI:10.1021/ol049655l

upstream raw materials:

2,6-difluoroiodobenzene

cyclopenta-1,3-diene

1-iodo-2,3-difluorobenzene

1,3-Difluorobenzene