Triphenylene

Base Information

• Chemical Name: Triphenylene
• CAS No.: 217-59-4
• Molecular Formula: C18H12
• Molecular Weight: 228.293
• Hs Code.: 29029090
• European Community (EC) Number: 205-922-9
• NSC Number: 57455
• UNII: 18WX3373I0
• DSSTox Substance ID: DTXSID9059757
• Nikkaji Number: J6.134D
• Wikipedia: Triphenylene
• Wikidata: Q2975866
• Metabolomics Workbench ID: 54806
• ChEMBL ID: CHEMBL1797416
• Mol file: 217-59-4.mol

Synonyms:1,2,3,4-Dibenznaphthalene;9,10-Benzophenanthrene;9,10-Benzphenanthrene;Benzo[l]phenanthrene;Isochrysene;NSC 57455;

Chemical Property of Triphenylene

Chemical Property:

• Appearance/Colour: white to beige crystalline needles
• Vapor Pressure: 4.9E-07mmHg at 25°C
• Melting Point: 195-198 °C(lit.)
• Refractive Index: 1.771
• Boiling Point: 424.998 °C at 760 mmHg
• Flash Point: 209.141 °C
• PSA: 0.00000
• Density: 1.19 g/cm³
• LogP: 5.14620
• Storage Temp.: 2-8°C
• Solubility.: Soluble in ethanol, benzene, acetic acid, oils and chloroform.
• Water Solubility.: 6.6ug/L(25.00 oC)
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 228.093900383
• Heavy Atom Count: 18
• Complexity: 217

Purity/Quality:

99% ^*data from raw suppliers

Triphenylene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi,N
• Statements: 41-50/53
• Safety Statements: 22-24/25-61-60-39-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C2C(=C1)C3=CC=CC=C3C4=CC=CC=C24
• Uses: Triphenylene is a polycyclic aromatic hydrocarbon (PAH) that can be isolated from coal tar. Triphenylene emits fluorescence in the ultraviolet region and is a useful compound for developing semiconductor devices.

Technology Process of Triphenylene

There total 274 articles about Triphenylene 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: 73.0%

carbon monoxide (201230-82-2) + 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) → triphenylene (217-59-4) + 9-fluorenone (486-25-9,952573-42-1) + 9,10-phenanthrenequinone (84-65-1)

Guidance literature:

Pt(dba)2*4PPh₃;

DOI:10.1021/ja011923c

Reference yield: 57.0%

2-bromobenzoic acid methyl ester (610-94-6) → benzoic acid methyl ester (93-58-3,5705-52-2,80226-58-0) + triphenylene (217-59-4) + diphenic acid dimethyl ester (5807-64-7)

Guidance literature:

With tetrabutyl-ammonium chloride; palladium diacetate; potassium carbonate; triphenylphosphine; In N,N-dimethyl-formamide; at 110 ℃; for 1h;

DOI:10.1016/j.tetlet.2008.09.017

Reference yield: 56.0%

2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) + phenylacetylene (536-74-3) → triphenylene (217-59-4) + diphenyl acetylene (501-65-5)

Guidance literature:

With copper(l) iodide; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In acetonitrile; at 80 ℃; for 12h; Inert atmosphere;

DOI:10.1039/b806821f

upstream raw materials:

tetrahydrofuran

n-butyllithium

fluorobenzene

diethyl ether

Downstream raw materials:

2-(triphenylene-2-carbonyl)-benzoic acid

o-tolyl-triphenylen-2-yl ketone

1,2,3,4,5,6,7,8,9,10,11,12-dodecahydrotriphenylene

benzenehexacarboxylic acid

Refernces

• 1、 Farina. "". . p. 2097. Retrieved 1963.
• 2、 Sato et al.. "". . p. 1994. Retrieved 1967.
• 3、 Gilman,Soddy. "-". . p. 1715. Retrieved 1957.
• 4、 Hirose, Takuji,Miyazaki, Yutaro,Watabe, Mizuki,Akimoto, Sho,Tachikawa, Tatsuya,Kodama, Koichi,Yasutake, Mikio. "Trialkylsilylethynyl-substituted triphenylenes and hexabenzocoronenes: Highly soluble liquid crystalline materials and their hole transport abilities". . p. 4714 - 4721. Retrieved 2015.
• 5、 Scola. "". . p. 405. Retrieved 1964.
• 6、 Tsuchiya, Shun,Saito, Hayate,Nogi, Keisuke,Yorimitsu, Hideki. "Aromatic Metamorphosis of Indoles into 1,2-Benzazaborins". . p. 3855 - 3860. Retrieved 2019.
• 7、 Kharasch et al. "". . p. 242. Retrieved 1965.
• 8、 Mao, Wenbin,Zhu, Chen. "C-C Bond (Hetero)arylation of Ring-Fused Benzocyclobutenols and Application in the Assembly of Polycyclic Aromatic Hydrocarbons". . p. 9133 - 9143. Retrieved 2017.
• 9、 Chatani,Kamitani,Oshita,Fukumoto,Murai. "Catalytic carbonylation reactions of benzyne derivatives". . p. 12686 - 12687. Retrieved 2001.
• 10、 Hilton, Cameron L.,Jamison, Christopher R.,King, Benjamin T.. "Uncatalyzed zirconium-mediated biphenylation of o-dihalobenzenes to form triphenylenes". . p. 14824 - 14824. Retrieved 2006.