2-Methyl-9,10-di(naphthalen-2-yl)anthracene

Base Information

• Chemical Name: 2-Methyl-9,10-di(naphthalen-2-yl)anthracene
• CAS No.: 804560-00-7
• Molecular Formula: C35H24
• Molecular Weight: 444.576
• Nikkaji Number: J2.103.496G
• Mol file: 804560-00-7.mol

Synonyms:804560-00-7;2-Methyl-9,10-di(naphthalen-2-yl)anthracene;MADN;2-METHYL-9,10-BIS(NAPHTHALEN-2-YL)ANTHRACENE;2-methyl-9,10-di(2-naphthyl)anthracene;2-methyl-9,10-dinaphthalen-2-ylanthracene;2-Methyl-9,10-bis(naphthalen-2-yl)anthracene;2-methyl-9,10-di(naphthalen-3-yl)anthracene;AMY31650;MFCD12022447;AKOS027339132;SB66725;AS-39351;FT-0763660;M2821;A21208;MADN , 2-Methyl-9,10-bis(naphthalen-2-yl)anthracene

Chemical Property of 2-Methyl-9,10-di(naphthalen-2-yl)anthracene

Chemical Property:

• Melting Point: 253-258°C
• Boiling Point: 607.2±50.0 °C(Predicted)
• PSA: 0.00000
• Density: 1.192±0.06 g/cm3 (20 oC 760 Torr)
• LogP: 9.94180
• XLogP3: 10.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 444.187800766
• Heavy Atom Count: 35
• Complexity: 709

Purity/Quality:

98% ^*data from raw suppliers

2-Methyl-9,10-di(2-naphthyl)anthracene >97.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C3=CC=CC=C3C(=C2C=C1)C4=CC5=CC=CC=C5C=C4)C6=CC7=CC=CC=C7C=C6
• Description: MADN, 2-methyl-9,10-bis(naphthalen-2-yl)anthracene is commonly known as a blue emitter. It is widely used?as a highly-efficient blue host material and hole-transporting material (HTM) for organic electronic devices. Exhibiting an ambipolar transporting ability, MADN offers stable thin-film morphology and a wide energy band-gap.
• Uses: Fluorescent host material in high efficiency blue OLED devices.

Technology Process of 2-Methyl-9,10-di(naphthalen-2-yl)anthracene

There total 7 articles about 2-Methyl-9,10-di(naphthalen-2-yl)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: 89.0%

2-bromonaphthalene (580-13-2) + 2-methyl-10-(2-naphthyl)-9-anthrone → 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (804560-00-7)

Guidance literature:

2-bromonaphthalene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

2-methyl-10-(2-naphthyl)-9-anthrone; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 2.5h;

Reference yield: 80.0%

naphthalene-2-boronic acid (32316-92-0) + 9,10-dibromo-2-methyl-anthracene (177839-45-1) → 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (804560-00-7)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In tetrahydrofuran; Inert atmosphere; Schlenk technique; Reflux;

DOI:10.1016/j.dyepig.2013.04.021

Reference yield:

2-methylanthracene-9,10-dione (84-54-8) → 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (804560-00-7)

Guidance literature:

Multi-step reaction with 3 steps

1: zinc; copper(ll) sulfate pentahydrate; ammonia / water / 85 °C / Inert atmosphere; Schlenk technique

2: N-Bromosuccinimide; trifluoroacetic acid / chloroform / 20 °C / Inert atmosphere; Schlenk technique

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran / Inert atmosphere; Schlenk technique; Reflux

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(ll) sulfate pentahydrate; ammonia; potassium carbonate; trifluoroacetic acid; zinc; In tetrahydrofuran; chloroform; water; 3: |Suzuki Coupling;

DOI:10.1016/j.dyepig.2013.04.021

upstream raw materials:

2-methylanthracene-9,10-dione

naphthalene-2-boronic acid

9,10-dibromo-2-methyl-anthracene

[1,4]naphthoquinone

Refernces

• 1、 Wang, Jianli,Leung, Louis M.. "Synthesis and characterization of highly soluble blue emitting poly(2-vinylanthracene) with 9,10-di(2-naphthalenyl) and 9,10-di(3-quinolinyl) substituents". . p. 105 - 115. Retrieved 2013/10/21.