Hexahelicene

Base Information

• Chemical Name: Hexahelicene
• CAS No.: 187-83-7
• Molecular Formula: C₂₆H₁₆
• Molecular Weight: 328.413
• NSC Number: 171474
• UNII: G5UR49H4NR
• DSSTox Substance ID: DTXSID80171964
• Nikkaji Number: J5.874B
• Wikidata: Q3135032
• Metabolomics Workbench ID: 54835
• Mol file: 187-83-7.mol

Synonyms:helicenes;hexahelicene

Chemical Property of Hexahelicene

Chemical Property:

• Vapor Pressure: 6.64E-14mmHg at 25°C
• Melting Point: 263-267 °C
• Boiling Point: 604.1°Cat760mmHg
• Flash Point: 314.6°C
• PSA: 0.00000
• Density: 1.263g/cm³
• LogP: 7.45260
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly, Sonicated)
• XLogP3: 7.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 328.125200510
• Heavy Atom Count: 26
• Complexity: 464

Purity/Quality:

99%, ^*data from raw suppliers

Hexahelicene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC3=C2C4=C(C=C3)C=CC5=C4C6=CC=CC=C6C=C5
• Uses: Hexahelicene, can be used in asymmetric polymerization of triphenylmethyl methacrylate by C2-chiral catalysts.

Technology Process of Hexahelicene

There total 38 articles about Hexahelicene 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: 92.0%

1,8-bis{2-[(1,3-dioxolan-2- yl)methyl]phenyl}naphthalene → [6]helicene (187-83-7,17486-32-7,19253-33-9)

Guidance literature:

With trifluorormethanesulfonic acid; at 0 - 20 ℃; for 0.666667h;

DOI:10.3762/BJOC.17.35

Reference yield: 86.0%

2-[(1Z)-1-buten-3-ynyl]-1-({2-[(1Z)-1-buten-3-ynyl]phenyl}ethynyl)naphthalene (457885-37-9) → [6]helicene (187-83-7,17486-32-7,19253-33-9)

Guidance literature:

bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/ja0259584

Reference yield: 85.0%

(Z)-1-Phenyl-2-(2-benzophenanthrenyl)ethylene (20508-11-6) + (E)-1-Phenyl-2-(2-benzophenanthrenyl)ethylene (20508-12-7) → [6]helicene (187-83-7,17486-32-7,19253-33-9)

Guidance literature:

With cholesteryl tetradecanoate; iodine; cholesteryl chloride; In neat (no solvent); at 80 ℃; for 2h; Irradiation;

DOI:10.1021/jo01314a044

upstream raw materials:

(Z)-1-Phenyl-2-(2-benzophenanthrenyl)ethylene

(E)-1-Phenyl-2-(2-benzophenanthrenyl)ethylene

2,7-distyrylnaphthalene

2-[(1Z)-1-buten-3-ynyl]-1-({2-[(1Z)-1-buten-3-ynyl]phenyl}ethynyl)naphthalene

Downstream raw materials:

hexahelicene-5,6-quinone

<6>-helicene

<6>-helicene

phenanthro[3,4c]phenanthrene

Refernces

• 1、 Ackermann, Lutz,Dhawa, Uttam,Hao, Jiping,Oliveira, Jo?o C. A.,Tian, Cong,Wdowik, Tomasz. "Enantioselective Pallada-Electrocatalyzed C?H Activation by Transient Directing Groups: Expedient Access to Helicenes". supporting information. p. 13451 - 13457. Retrieved 2020/06/10.
• 2、 Talele, Harish R.,Chaudhary, Anju R.,Patel, Parthiv R.,Bedekar, Ashutosh V.. "Expeditious synthesis of helicenes using an improved protocol of photocyclodehydrogenation of stilbenes". experimental part. p. 15 - 37. Retrieved 2011/06/19.