15810-14-7

Basic information

• Product Name: 9,10-DIETHYLPHENANTHRENE
• Synonyms: 9,10-DIETHYLPHENANTHRENE
• CAS NO: 15810-14-7
• Molecular Formula: C₁₈H₁₈
• Molecular Weight: 234.34
• Mol File: 15810-14-7.mol

Chemical Properties

• Boiling Point: 384.8°C at 760 mmHg
• Flash Point: 179.7°C
• Appearance: /
• Density: 1.049g/cm³
• Vapor Pressure: 8.84E-06mmHg at 25°C
• Refractive Index: 1.645
• CAS DataBase Reference: 9,10-DIETHYLPHENANTHRENE(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-DIETHYLPHENANTHRENE(15810-14-7)
• EPA Substance Registry System: 9,10-DIETHYLPHENANTHRENE(15810-14-7)

Safety Data

• Hazardous Substances Data: 15810-14-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H18/c1-3-13-14(4-2)16-10-6-8-12-18(16)17-11-7-5-9-15(13)17/h5-12H,3-4H2,1-2H3

Upstream product

• 50703-58-7 2,2'-Dipropionyl-biphenyl 
• 859951-12-5 9,10-diacetyl-phenanthrene 
• 14619-90-0 9,10-diethyl-9,10-dihydro-phenanthrene-9,10-diol 
• 98766-77-9 1,2,3,4,5,8-Hexahydro-3-hyroxy-9,10-diethyl-phenanthren 
• 5561-92-2 1-(2-methoxyphenyl)propan-1-one 
• 17918-49-9 9-Brom-10-ethyl-phenanthren 
• 75-03-6 ethyl iodide 
• 928-49-4 hex-3-yne 
• 2052-07-5 2-Bromobiphenyl 
• 13029-09-9 2,2'-dibromobiphenyl 
• 591-51-5 phenyllithium 
• 85-01-8 phenanthrene 
• 103441-58-3 1-(2-iodophenyl)propan-1-one 
• 573-17-1 9-bromophenanthrene 

Relevant articles and documents

A Theoretical Study on the Mechanism of the Oxidative Deborylation/C-C Coupling Reaction of Borepin Derivatives

One-electron oxidation of borepin derivatives that consists of a boron-containing seven-membered ring has been reported to cause deborylation/C-C coupling, yielding aromatic compounds. The reaction can be achieved not only by transition metal compounds but also by oxidants without transition metal such as O2 and other organic compounds. Despite numerous experimental attempts, the mechanism of this peculiar reaction as well as the fate of the BCl part eliminated from borepin remain unclear to date. Based on theoretical approaches using the artificial force induced reaction method, here we address the mechanism of the unusual boron-mediated C-C coupling. For this purpose, two borepin derivatives (1 and 35), bearing ethyl and phenyl groups, respectively, were used as reactants, and FeCl3/MeNO2 and O2 were chosen as oxidants. The calculations revealed reaction pathways that provided an overall picture of the mechanism of the target reaction, which features four key steps, namely, (i) quaternization of the boron atom by the coordination of oxidant, (ii) intersystem crossing, (iii) skeletal rearrangement to form a six-membered ring, and (iv) elimination of a boron moiety. The intrinsic nature of boron, i.e., a strong tendency to accept a coordination ligand even under oxidative conditions, is responsible for the oxidative deborylation/C-C coupling of borepin.

Phenanthrene Synthesis by Palladium(II)-Catalyzed γ-C(sp2)-H Arylation, Cyclization, and Migration Tandem Reaction

Phenanthrene is an important structural motif in chemistry and materials science, and many synthetic routes have been developed to construct its skeleton. However, synthesis of unsymmetric phenanthrenes remains a challenge. Here, an efficient one-pot tandem reaction for the preparation of phenanthrenes via sequential γ-C(sp2)-H arylation, cationic cyclization, dehydration, and 1,2-migration was developed. A wide range of symmetric and unsymmetric phenanthrenes with diversified functional groups were synthesized with good to excellent yields.

Zirconacyclopentadiene-Annulated Polycyclic Aromatic Hydrocarbons

Syntheses of large polycyclic aromatic hydrocarbons (PAHs) and graphene nanostructures demand methods that are capable of selectively and efficiently fusing large numbers of aromatic rings, yet such methods remain scarce. Herein, we report a new approach

Synthesis of multiply substituted polycyclic aromatic hydrocarbons by iridium-catalyzed annulation of ring-fused benzocyclobutenol with alkyne through C-C bond cleavage

The first iridium-catalyzed intermolecular cyclization between alkynes and ring-fused benzocyclobutenols (RBCB) through C-C bond cleavage is described. A variety of elusive polycyclic aromatic hydrocarbons (PAHs) with multiple substituents are obtained in good yields under mild conditions. This procedure provides a unique and expeditious tool for the synthesis of PAHs. Expanding the family: The iridium-catalyzed intermolecular cyclization between ring-fused benzocyclobutenols and alkynes through C-C bond cleavage is described. A variety of elusive polycyclic aromatic hydrocarbons (PAHs) with multiple substituents are obtained in good yields under mild conditions. The transformation exhibits good functional-group tolerance and regioselectivity.

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.

Salt/ligand-activated low-valent titanium formulations: the 'salt effect' on diastereoselective carbon-carbon bond forming SET reactions

A comprehensive study on the influence of exogenously added electropositive metal salts as promoters/secondary activators on preformed LVT species has resulted in the construction of highly efficient low-valent titanium (LVT) reagents. These salt-activated LVT reagents while exhibiting enhanced chemoselectivity and diastereoselectivity accelerated the reductive olefination rates of aromatic and aliphatic carbonyls under ambient temperature conditions and in much reduced reaction times. The versatility of the salted reagent was further explored in other single electron transfer reactions, namely, imino-pinacol couplings and one-pot synthesis of phenanthrenes from o-alkoxy aromatic carbonyls. We envisage that, in contrast to multiphase heterogeneous colloidal slurries, salt-activated LVT reagents afforded uniformly viscous homogeneous slurries generating a highly reactive monomeric intermetallic LVT complex. Continued judicious exploration of the emerging paradigms by studying the influence of external ligands/auxiliaries/redox agents on LVT reagents, and organometallics in general, will be critical to widen the scope and utility of the classical McMurry reaction and other SET reactions.

Generation of benzocyclobutadiene derivatives from zirconaindene derivatives

Zirconaindene derivatives produced benzocyclobutadiene derivatives in situ in the presence of CuCl and 1,4-naphthoquinone, which afforded their dimers, 6a, 10b-dihydrobenzo[a]biphenylenes and dibenzosemibullvalenes or dibenzo[a,e]-cycloctenes.

Chromium-mediated synthesis of polycyclic aromatic compounds from halobiaryls

(Chemical Equation Presented) Reaction of 2,2′-dihalobiphenyl with butyllithium followed by the addition of chromium(III) chloride and alkynes afforded the corresponding phenanthrene derivatives via formal [4 + 2] cycloaddition. A variety of alkynes could be used for this reaction, such as alkyl, aryl, silyl, and alkoxycarbonyl alkynes. Repetitive process of the reaction gave more extended polycyclic compounds such as benzo[g]chrysene and azacyclopentaphenalene derivatives.

Highly active salted low-valent titanium reagents for various SET induced reactions

External addition of inorganic salts (Group I and II metal halides) to the preformed low-valent titanium reagent A (TiCl3-Li-THF) dramatically enhanced its activity. The new reagents were used to carry out various SET reactions including McMurry's olefination at a faster rate even at ambient temperature.

Characterization of the combustion products of polyethylene

Polyethylene (PE) was burned in a tube-type furnace with an air flow at a temperature of 600~900°C. Combustion products were collected with glass wool, glass fiber filter, and XAD-2 adsorbent. The analysis of the products was performed with GC-FID and GC-MSD. At low temperature, hydrocarbons were the major components, while at higher temperature the products were composed of polycyclic aromatic hydrocarbons. With the high performance of the Hewlett-Packard 6890GC-5973MSD, more compounds were identified in comparison with previous studies.