9-Ethynylanthracene

Base Information

• Chemical Name: 9-Ethynylanthracene
• CAS No.: 13752-40-4
• Molecular Formula: C16H10
• Molecular Weight: 202.255
• Hs Code.: 2902909090
• DSSTox Substance ID: DTXSID10399811
• Nikkaji Number: J492.344H
• Wikidata: Q82202557
• Mol file: 13752-40-4.mol

Synonyms:9-ethynylanthracene;13752-40-4;Anthracene, 9-ethynyl-;9-ETHYNYL-ANTHRACENE;9-anthryl ethyne;9-ethynyl Anthracene;DTXSID10399811;WSZBYXQREMPYLP-UHFFFAOYSA-N;F72815;A1-15016

Chemical Property of 9-Ethynylanthracene

Chemical Property:

• Melting Point: 72.5-76 °C
• Boiling Point: 377.7±11.0 °C(Predicted)
• PSA: 0.00000
• Density: 1.15±0.1 g/cm3(Predicted)
• LogP: 3.97430
• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 202.078250319
• Heavy Atom Count: 16
• Complexity: 272

Purity/Quality:

95% ^*data from raw suppliers

9-Ethynylanthracene 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CC1=C2C=CC=CC2=CC3=CC=CC=C31

Technology Process of 9-Ethynylanthracene

There total 18 articles about 9-Ethynylanthracene 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: 99.0%

[2-(anthracen-9-yl)ethynyl]trimethylsilane (104784-61-4) → 9-ethynylanthracene (13752-40-4)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; methanol; for 8h;

DOI:10.1021/ol016414u

Reference yield: 96.0%

9-(2,2-dibromovinyl)anthracene (77295-65-9) → 9-ethynylanthracene (13752-40-4)

Guidance literature:

With Succinimide; potassium carbonate; In dimethyl sulfoxide; at 90 ℃; for 2h; Schlenk technique; Inert atmosphere;

DOI:10.1016/j.tetlet.2021.153051

Reference yield: 91.0%

carbon tetrabromide (558-13-4) + 9-anthracene aldehyde (642-31-9) → 9-ethynylanthracene (13752-40-4)

Guidance literature:

carbon tetrabromide; 9-anthracene aldehyde; With triisopropyl phosphite; In acetonitrile; at 0 ℃; for 0.166667h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium hydroxide; In acetonitrile; at 0 - 20 ℃; for 4h;

DOI:10.1002/adsc.201801334

upstream raw materials:

9-(2-chloroethenyl)anthracene

9-(1,2-dibromoethyl)anthracene

9-(α-Chlorvinyl)anthracen

[2-(anthracen-9-yl)ethynyl]trimethylsilane

Downstream raw materials:

9-[(2-ethynylphenyl)ethynyl]anthracene

9-(3-phenylnaphthalen-2-yl)anthracene

2-(anthracen-9-ylethynyl)benzaldehyde

Refernces

• 1、 Gutieì?rrez-Arzaluz, Luis,Guarin, Cesar A.,Rodriì?guez-Coì?rdoba, William,Peon, Jorge. "Dynamics of the formation of a charge transfer state in 1,2-bis(9-anthryl)acetylene in polar solvents: Symmetry reduction with the participation of an intramolecular torsional coordinate". . p. 12175 - 12183. Retrieved 2013.
• 2、 Takahashi, Kan,Ito, Shun,Nakamoto, Kosuke,Ito, Yasutomo,Ueno, Yoshihito. "Photoinduced Electron-Transfer-Based Hybridization Probes for Detection of DNA and RNA". . p. 8561 - 8570. Retrieved 2015.
• 3、 Zhao, Zujin,Yu, Shuqiang,Xu, Lei,Wang, Hongbo,Lu, Ping. "Novel, yellow-emitting anthracene/fluorene oligomers: synthesis and characterization". . p. 7809 - 7815. Retrieved 2007.
• 4、 Daniele, Michael A.,Bandera, Yuriy P.,Foulger, Stephen H.. "Manipulation of Foerster energy transfer of coupled fluorophores through biotransformation by Pseudomonas resinovorans CA10". . p. 129 - 134. Retrieved 2012.
• 5、 Baumann, Christoph,Centeno, Silvia P.,G?stl, Robert,Stratigaki, Maria. "Multicolor Mechanofluorophores for the Quantitative Detection of Covalent Bond Scission in Polymers". . p. 13287 - 13293. Retrieved 2021.
• 6、 Islam, Khadimul,Narjinari, Himani,Bisarya, Akshara,Kumar, Akshai. "Multi-fold Sonogashira coupling: A new and convenient approach to obtain tetraalkynyl anthracenes with tunable photophysical properties". . p. 9692 - 9704. Retrieved 2021/11/30.