2',5'-Diiodo-P-terphenyl

Base Information

• Chemical Name: 2',5'-Diiodo-P-terphenyl
• CAS No.: 96843-21-9
• Molecular Formula: C18H12I2
• Molecular Weight: 482.102
• Hs Code.: 2903999090
• DSSTox Substance ID: DTXSID30539777
• Wikidata: Q82415579
• Mol file: 96843-21-9.mol

Synonyms:2',5'-DIIODO-P-TERPHENYL;96843-21-9;1,4-diiodo-2,5-diphenylbenzene;SCHEMBL7803626;DTXSID30539777;2~2~,2~5~-Diiodo-1~1~,2~1~:2~4~,3~1~-terphenyl

Chemical Property of 2',5'-Diiodo-P-terphenyl

Chemical Property:

• PSA: 0.00000
• LogP: 6.22980
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 481.90285
• Heavy Atom Count: 20
• Complexity: 262

Purity/Quality:

99% ^*data from raw suppliers

2',5'-DIIODO-P-TERPHENYL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC(=C(C=C2I)C3=CC=CC=C3)I

Technology Process of 2',5'-Diiodo-P-terphenyl

There total 7 articles about 2',5'-Diiodo-P-terphenyl 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: 95.0%

2',5'-bis(trimethylsilyl)-1,1':4',1''-terphenyl → 2',5'-diiodo-1,1':4',1''-terphenyl (96843-21-9)

Guidance literature:

With Iodine monochloride; In dichloromethane; chloroform; for 1h;

DOI:10.1021/ja075260w

Reference yield:

1,4-dibromo-2,5-diiodobenzene (63262-06-6) + phenylmagnesium bromide → iodobenzene (591-50-4) + 2',5'-diiodo-1,1':4',1''-terphenyl (96843-21-9)

Guidance literature:

With iodide; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, RT, 2 h, 2) THF, 10 deg C, 1 h;

DOI:10.1021/jo00217a018

Reference yield:

1.4-dibromobenzene (106-37-6) → 2',5'-diiodo-1,1':4',1''-terphenyl (96843-21-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / iodine / H₂SO₄ / 6 h / 125 - 135 °C

2: 2.) iodine / 1.) THF, room temperature

With iodine; In sulfuric acid;

DOI:10.1016/S0040-4039(00)98457-0

upstream raw materials:

1,4-dibromo-2,5-diiodobenzene

1.4-dibromobenzene

2,5-diiodo-1,4-phenylenebistrimethylsilane

phenylboronic acid

Refernces

An efficient convergent synthesis of novel anisotropic adsorbates based on nanometer-sized and tripod-shaped oligophenylenes end-capped with triallylsilyl groups

10.1021/jo0257750

The research focuses on the efficient convergent synthesis of a novel tripod-shaped oligophenylene compound, designed as a new type of anisotropic adsorbate for controlling the orientation and spacing of functional groups in organic thin films and nanostructures on silicon surfaces. The compound is composed of three oligophenylene heptamers as legs, a bromophenyl group as a functional arm, and a tetrahedron silicon atom as the central node, with each leg end-capped with a triallylsilyl group for covalent anchoring on hydrogen-terminated silicon surfaces via hydrosilylation. The synthesis involved a series of palladium-catalyzed coupling reactions, including Suzuki coupling, and optimization of reaction conditions to achieve selective coupling and high yields. Key reactants included diiodoterphenyl, bromophenyl boronic acid, and various organosilicon compounds. Analytical techniques used to characterize the synthesized compounds included NMR spectroscopy, mass spectrometry (MALDI-TOF MS), and gel permeation chromatography. The research also encountered challenges in introducing dendrons to the tripod legs, leading to further exploration of alternative synthetic routes.

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