9,10-Bis(phenylethynyl)anthracene

Base Information

• Chemical Name: 9,10-Bis(phenylethynyl)anthracene
• CAS No.: 10075-85-1
• Molecular Formula: C30H18
• Molecular Weight: 378.473
• Hs Code.: 29029090
• European Community (EC) Number: 233-210-8
• UNII: FC8JDB70DQ
• DSSTox Substance ID: DTXSID3064936
• Nikkaji Number: J236.270H
• Wikipedia: 9,10-Bis(phenylethynyl)anthracene
• Wikidata: Q274980
• Metabolomics Workbench ID: 57833
• Mol file: 10075-85-1.mol

Synonyms:9,10-bis(phenylethynyl)anthracene;BPEA cpd

Chemical Property of 9,10-Bis(phenylethynyl)anthracene

Chemical Property:

• Appearance/Colour: orange crystalline powder
• Vapor Pressure: 2.3E-14mmHg at 25°C
• Melting Point: 252-258 °C
• Refractive Index: 1.753
• Boiling Point: 614.3 °C at 760 mmHg
• Flash Point: 325.6 °C
• PSA: 0.00000
• Density: 1.23 g/cm³
• LogP: 6.79260
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Light Sensitive
• Water Solubility.: It is insoluble in water but is soluble in most organic solvents such as carbon disulfide, alcohols, benzene, chloroform, and hy
• XLogP3: 8.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 378.140850574
• Heavy Atom Count: 30
• Complexity: 605

Purity/Quality:

99% ^*data from raw suppliers

9,10-Bis(phenylethynyl)anthracene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C#CC2=C3C=CC=CC3=C(C4=CC=CC=C42)C#CC5=CC=CC=C5
• Uses: 9,10-Bis(phenylethynyl)anthracene is known to exert fluorescence properties due to its polycyclic aromatic hydrocarbon system and it is commonly used as an scintillator additive. 9,10-Bis(phenylethyny l)anthracene was also studied extensively as a fluorescence emitters for peroxyoxalate chemiluminescence. 9,10-Bis(phenylethynyl)anthracene is used as a?chemiluminescent?fluorophore?with high?quantum efficiency. It is used in lightsticks as a fluorophor producing ghostly green light. It is also used as a dopant for organic semiconductors in OLEDs. It is used as a reagent for chemiluminescence research. 9,10-Bis(phenylethynyl)anthracene is known to exert fluorescence properties due to its polycyclic aromatic hydrocarbon system and it is commonly used as an scintillator additive. 9,10-Bis(phenylethynyl)anthracene was also studied extensively as a fluorescence emitters for peroxyoxalate chemiluminescence. Reagent for chemiluminescence research.

Technology Process of 9,10-Bis(phenylethynyl)anthracene

There total 26 articles about 9,10-Bis(phenylethynyl)anthracene 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: 100.0%

9,10-Dibromoanthracene (523-27-3) + phenylacetylene (536-74-3) → 9,10-diphenylethynylanthracene (10075-85-1)

Guidance literature:

With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; at 89 ℃; for 3h;

DOI:10.1246/bcsj.57.752

Reference yield: 99.0%

9,10-bis(phenylethynyl)-9,10-dihydro-9,10-epidioxidoanthracene (32287-35-7) → 9,10-diphenylethynylanthracene (10075-85-1)

Guidance literature:

In chloroform-d1; at 20 ℃; for 1.5h;

DOI:10.1002/poc.3607

Reference yield: 98.0%

Benzyl phenyl sulfone (3112-88-7) + 10-(phenylethynyl)-9-anthracenecarbaldehyde → 9,10-diphenylethynylanthracene (10075-85-1)

Guidance literature:

With diethyl chlorophosphate; lithium hexamethyldisilazane; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1055/s-0032-1316867

upstream raw materials:

9,10-bis(phenylethynyl)-9,10-dihydroanthracene-9,10-diol

9-(α,β-dichloro-styryl)-10-phenylethynyl-anthracene

9,10-Dibromoanthracene

Bis(phenylethynyl)magnesium

Downstream raw materials:

9,10-bis(phenylacetyl)anthracene

9-phenylacetyl-10-(phenylethynyl)anthracene

(E,E)-9,10-Bis(styryl)anthracene

9-cis-styryl-10-trans-anthracene

Refernces

• 1、 Fudickar, Werner,Linker, Torsten. "Why triple bonds protect acenes from oxidation and decomposition". . p. 15071 - 15082. Retrieved 2012.
• 2、 Goldberg,Bard. "-". . p. 139,140,141. Retrieved 1970.
• 3、 Fuerstner, Alois,Seidel, Guenter. "Palladium-Catalyzed Arylation of Polar Organometallics Mediated by 9-Methoxy-9-Borabicyclononane: Suzuki Reactions of Extended Scope". . p. 11165 - 11176. Retrieved 1995.
• 4、 Zhong, Fangfang,Zhao, Jianzhang. "Phenyleneanthracene derivatives as triplet energy acceptor/emitter in red light excitable triplet-triplet-annihilation upconversion". . p. 909 - 918. Retrieved 2017.
• 5、 Xue, Tanlong,Zhao, Di,Hao, Tingting,Li, Xiuyan,Wang, Tao,Nie, Jun. "Synthesis, one/two-photon optical and electrochemical properties and the photopolymerization-sensitizing effect of anthracene-based dyes: Influence of the donor groups". . p. 6737 - 6745. Retrieved 2019/05/10.