Naphthacene

Base Information

• Chemical Name: Naphthacene
• CAS No.: 92-24-0
• Molecular Formula: C18H12
• Molecular Weight: 228.293
• Hs Code.: 29029090
• European Community (EC) Number: 202-138-9
• UNII: QYJ5Z6712R
• DSSTox Substance ID: DTXSID4059045
• Nikkaji Number: J1.536.811J,J4.651E
• Wikipedia: Tetracene
• Wikidata: Q379089
• Metabolomics Workbench ID: 54638
• ChEMBL ID: CHEMBL1797272
• Mol file: 92-24-0.mol

Synonyms:2,3-benzanthracene;2,3-benzanthrene;benz(b)anthracene;naphthacene;rubene;tetracene

Chemical Property of Naphthacene

Chemical Property:

• Appearance/Colour: orange powder
• Vapor Pressure: 2.02E-07mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 436.7°C at 760 mmHg
• Flash Point: 209.1°C
• PSA: 0.00000
• Density: 1.19g/cm³
• LogP: 5.14620
• Water Solubility.: 1.507ug/L(25 oC)
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 228.093900383
• Heavy Atom Count: 18
• Complexity: 236

Purity/Quality:

Naphthacene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,N
• Statements: 40-50/53
• Safety Statements: 45-36/37-61-60-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C2C=C3C=C4C=CC=CC4=CC3=CC2=C1
• Uses: p-Type organic conductor and OLED dopant. Sublimed grade for organic electronic device applications. Naphthacene is a polycyclic aromatic hydrocarbon. Naphthacene is often used as a molecular organic semiconductor in organic field-effect transistors and organic light-emitting diodes. Naphthacene is a lso used in various applications involving the enhancement of photocurrent. Naphthacene is a polycyclic aromatic hydrocarbon. Naphthacene is often used as a molecular organic semiconductor in organic field-effect transistors and organic light-emitting diodes. Naphthacene is also used in various applications involving the enhancement of photocurrent.

Technology Process of Naphthacene

There total 92 articles about Naphthacene 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: 95.0%

5,12-dihydro-naphthacene (959-02-4) → Tetracen (92-24-0)

Guidance literature:

palladium on activated charcoal; In xylene; for 48h; Heating;

DOI:10.1021/jo00231a001

Reference yield: 85.0%

13-methyl-5,12-dihydronaphthacen-5,12-imine (85894-23-1) → Tetracen (92-24-0)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In acetonitrile; for 2h; Heating;

DOI:10.1021/jo00162a013

Reference yield: 83.0%

5,12-(H)-Naphthacenone (3073-99-2) → Tetracen (92-24-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h; Ambient temperature;

DOI:10.1021/jo00358a007

upstream raw materials:

5,12-dihydro-naphthacene

6-hydroxy-naphthacene-5,12-dione

tetrahydro-1,2,3,4 naphtacene

5,11-dichlorotetracene

Downstream raw materials:

5,12-naphthacenequinone

5,12-dihydro-naphthacene

5,11-dibromonaphthacene

tetrathiatetracene

Refernces

• 1、 Woodward, Simon,Ackermann, Miriam,Ahirwar, Saurabh K.,Burroughs, Laurence,Garrett, Mary Robert,Ritchie, John,Shine, Jonathan,Tyril, Bj?rk,Simpson, Kevin,Woodward, Peter. "Straightforward Synthesis of 2- and 2,8-Substituted Tetracenes". . p. 7819 - 7824. Retrieved 2017/06/06.
• 2、 Geary, Laina M.,Chen, Te-Yu,Montgomery, T. Patrick,Krische, Michael J.. "Benzannulation via ruthenium-catalyzed diol-diene [4+2] cycloaddition: One- and two-directional syntheses of fluoranthenes and acenes". . p. 5920 - 5922. Retrieved 2014/05/20.