19027-68-0

Basic information

• Product Name: 5-methyl-1,2,3,4-tetraphenylnaphthalene
• CAS NO: 19027-68-0
• Molecular Formula: C₃₅H₂₆
• Molecular Weight: 446.5809
• Mol File: 19027-68-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 500.6°C at 760 mmHg
• Flash Point: 259.7°C
• Density: 1.113g/cm³
• Vapor Pressure: 1.16E-09mmHg at 25°C
• Refractive Index: 1.655
• CAS DataBase Reference: 5-methyl-1,2,3,4-tetraphenylnaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methyl-1,2,3,4-tetraphenylnaphthalene(19027-68-0)
• EPA Substance Registry System: 5-methyl-1,2,3,4-tetraphenylnaphthalene(19027-68-0)

Safety Data

• Hazardous Substances Data: 19027-68-0(Hazardous Substances Data)

Upstream product

• 5100-98-1 1-chloro-2-iodo-3-methylbenzene 
• 479-33-4 2,3,4,5-tetraphenylcyclopenta-2,4-dienone 
• 76054-67-6 (1R,8S)-3,11,11-Trimethyl-1,8,9,10-tetraphenyl-11-germa-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5,9-tetraene 
• 32768-54-0 2,3-dichlorotoluene 
• 101300-65-6 1,2-bis(trimethylsilyl)-3-methylbenzene 
• 501-65-5 diphenyl acetylene 
• 108-88-3 toluene 
• 16419-60-6 2-Methylphenylboronic acid 
• 4792-30-7 3-methylphthalic acid anhydride 
• 95-46-5 2-methylphenyl bromide 

Relevant articles and documents

Group 4 Diarylmetallocenes as Bespoke Aryne Precursors for Titanium-Catalyzed [2 + 2 + 2] Cycloaddition of Arynes and Alkynes

Despite the ubiquity of reports describing titanium (Ti)-catalyzed [2 + 2 + 2] cyclotrimerization of alkynes, the incorporation of arynes into this potent manifold has never been reported. The in situ generation of arynes often requires fluoride, which instead will react with the highly fluorophilic Ti center, suppressing productive catalysis. Herein, we describe the use of group 4 diarylmetallocenes, CpR2MAr2 (CpR = C5H5, C5Me5; M = Ti, Zr), as aryne precursors for the Ti-catalyzed synthesis of substituted naphthalenes via coupling with 2 equiv of an alkyne. Fair-to-good yields of the desired naphthalene products could be obtained with 1% catalyst loadings, which is roughly an order of magnitude lower than similar reactions catalyzed by palladium or nickel. Additionally, naphthalenes find broad applications in the electronics, photovoltaics, and pharmaceutical industries, urging the discovery of more economic syntheses. These results indicate that aryne transfer from a CpR2M(?2-aryne) complex to another metal is a viable route for the introduction of aryne fragments into organometallic catalytic processes.

Three-bond breaking of cyclic anhydrides: Easy access to polyfunctionalized naphthalenes and phenanthrenes

Benzannulation of phthalic anhydrides with alkynes to polyfunctionalized naphthalenes and phenanthrenes was confirmed to be straightforward using a palladium catalytic system. Sequential liberation of CO2 and CO occurred via oxidative decomposition of anhydride. In the case of 1,8-naphthalenedicarboxylic anhydrides, both aryls were encompassed in the annulation reaction to afford acenaphthylenes.

Synthesis of highly substituted naphthalene and anthracene derivatives by rhodium-catalyzed oxidative coupling of arylboronic acids with alkynes

The rhodium-catalyzed oxidative 1:2 coupling reactions of arylboronic acids with alkynes effectively proceeds in the presence of a copper-air oxidant to produce the corresponding annulated products. Of special note, anthracene derivatives can be obtained