1,8-Diiodonaphthalene

Base Information

• Chemical Name: 1,8-Diiodonaphthalene
• CAS No.: 1730-04-7
• Molecular Formula: C10H6I2
• Molecular Weight: 379.967
• Hs Code.: 2903999090
• Mol file: 1730-04-7.mol

Synonyms:Naphthalene,1,8-diiodo-;

Chemical Property of 1,8-Diiodonaphthalene

Chemical Property:

• Melting Point: 109-113°C
• Boiling Point: 384.2 °C at 760 mmHg
• Flash Point: 204.3 °C
• PSA: 0.00000
• Density: 2.265 g/cm³
• LogP: 4.04900

Purity/Quality:

97% ^*data from raw suppliers

1,8-Diiodonaphthalene ≥98.0% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 22-50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• General Description: 1,8-Diiodonaphthalene exhibits significant structural distortion due to repulsion between the iodine substituents, with a small twist angle (ω = 2°–17°) and an interatomic distance (d(I···I) = 3.51–3.54 ?) that is only 82% of the sum of van der Waals radii. This distortion results from balanced charge distribution and intramolecular repulsion, with estimated repulsion energy of ~30 kJ mol-1 and reduced π-delocalization energy of ~10 kJ mol-1. Additionally, it serves as a versatile precursor in palladium-catalyzed aminocarbonylation reactions to form dicarboxamides or N-substituted imides, depending on reaction conditions.

Technology Process of 1,8-Diiodonaphthalene

There total 5 articles about 1,8-Diiodonaphthalene 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: 80.0%

Naphthalene-1,8-dicarboxylic acid (518-05-8) → 1,8-diiodonaphthalene (1730-04-7)

Guidance literature:

With [bis(acetoxy)iodo]benzene; iodine; In tetrachloromethane; for 2h; Heating; Irradiation;

Reference yield: 70.0%

naphthalene-1,8-diamine (479-27-6) → 1,8-diiodonaphthalene (1730-04-7)

Guidance literature:

With sulfuric acid; 7,14-bis(trimethylsilyl)acenaphtho[1,2-k]fluoranthene; sodium nitrite; In water; at -20 - 80 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/chem.201902915

Reference yield: 57.0%

1-naphthalenecarboxylic acid (86-55-5) → 1,8-diiodonaphthalene (1730-04-7) + 1-Iodonaphthalene (90-14-2)

Guidance literature:

With potassium phosphate; iodine; In acetonitrile; at 140 ℃; for 16h; chemoselective reaction; Glovebox; Inert atmosphere;

DOI:10.1021/jacs.7b05155

upstream raw materials:

naphthalene-1,8-diamine

Naphthalene-1,8-dicarboxylic acid

1-naphthalenecarboxylic acid

Downstream raw materials:

PERYLENE

1,8-bis((p-tolyl)ethynyl)naphthalene

9-Methyl-7-p-tolyl-benzo[k]fluoranthene

7-o-Tolyl-11-methyl-benzofluoranthen