1,3-Dichloro-5-[2-(4-chlorophenyl)ethenyl]benzene

Base Information

• Chemical Name: 1,3-Dichloro-5-[2-(4-chlorophenyl)ethenyl]benzene
• CAS No.: 688348-25-6
• Molecular Formula: C14H9Cl3
• Molecular Weight: 283.58
• DSSTox Substance ID: DTXSID20694021
• Mol file: 688348-25-6.mol

Synonyms:PDM-2;PDM 2;DTXSID20694021;BCP29875;1,3-Dichloro-5-[2-(4-chlorophenyl)ethenyl]benzene

Chemical Property of 1,3-Dichloro-5-[2-(4-chlorophenyl)ethenyl]benzene

Chemical Property:

• Boiling Point: 394.2±42.0 °C(Predicted)
• PSA: 0.00000
• Density: 1.360±0.06 g/cm3(Predicted)
• LogP: 5.81720
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 281.976983
• Heavy Atom Count: 17
• Complexity: 246

Purity/Quality:

97% ^*data from raw suppliers

PDM2 >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC2=CC(=CC(=C2)Cl)Cl)Cl
• Description: The aryl hydrocarbon receptor (AhR) is a ligand-dependent intracellular transcription factor whose ligands include some of the most infamous xenobiotics, including dioxin, benzo[a]pyrene, and numerous polyaromatics from soot and coal tar. PDM 2 is an analog of resveratrol acting as a potent and selective aryl hydrocarbon receptor (AhR) antagonist, with a Ki of 1.2 nM. PDM 2 is inactive as a ligand for the estrogen receptor even at 100 μM. As AhR knockout mice are insensitive to the carcinogenic effects of classical AhR ligands, PDM 2 is a potential therapeutic for the treatment for dioxin and other aryl hydrocarbon poisonings.

Technology Process of 1,3-Dichloro-5-[2-(4-chlorophenyl)ethenyl]benzene

There total 2 articles about 1,3-Dichloro-5-[2-(4-chlorophenyl)ethenyl]benzene 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: 18.0%

4-chlorobenzaldehyde (104-88-1) + (3,5-dichlorobenzyl)-triphenylphosphonium bromide (88812-21-9) → 1,3-dichloro-5-[(1E)-2-(4-chlorophenyl)ethenyl]benzene (688348-25-6) + (Z)-1,3-dichloro-5-(4-chlorostyryl)benzene (688348-25-6)

Guidance literature:

(3,5-dichlorobenzyl)-triphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

4-chlorobenzaldehyde; In tetrahydrofuran; hexane; at -60 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.bmcl.2017.05.025

Reference yield: 18.0%

4-chlorobenzaldehyde (104-88-1) + (3,5-dichlorobenzyl)-triphenylphosphonium bromide (88812-21-9) → 1,3-dichloro-5-[(1E)-2-(4-chlorophenyl)ethenyl]benzene (688348-25-6) + (Z)-1,3-dichloro-5-(4-chlorostyryl)benzene (688348-25-6)

Guidance literature:

(3,5-dichlorobenzyl)-triphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

4-chlorobenzaldehyde; In tetrahydrofuran; hexane; at -60 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.bmcl.2017.05.025

upstream raw materials:

4-chlorobenzaldehyde

(3,5-dichlorobenzyl)-triphenylphosphonium bromide