613-12-7

Usage

Chemical Properties

BEIGE TO LIGHT YELLOW-BROWN CRYSTALLINE POWDER

Uses

2-Methylanthracene (cas# 613-12-7) is a compound useful in organic synthesis.

Source

Detected in 8 diesel fuels at concentrations ranging from 0.18 to 160 mg/L with a mean value of 46.16 mg/L (Westerholm and Li, 1994). Schauer et al. (1999) reported 2- methylanthracene in diesel fuel at a concentration of 6 μg/g and in a diesel-powered medium-duty truck exhaust at an emission rate of 10.4 μg/km. California Phase II reformulated gasoline contained naphthalene at a concentration of 5.54 g/kg. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were approximately 1.14 and 94.1 μg/km, respectively (Schauer et al., 2002).

Environmental fate

Chemical/Physical. 2-Methylanthracene will not hydrolyze because it has no hydrolyzable functional group.

Purification Methods

Chromatograph it on silica gel with cyclohexane as eluent and then recrystallise it from EtOH [Werst J Am Chem Soc 109 32 1987]. [Beilstein 5 IV 2311.]

InChI:InChI=1/C15H12/c1-11-14-8-4-2-6-12(14)10-13-7-3-5-9-15(11)13/h2-10H,1H3

Upstream product

• 100-42-5 styrene 
• 56-23-5 tetrachloromethane 
• 13540-50-6 2-benzyl-1,4-dimethylbenzene 
• 4044-60-4 2,5-dimethylbenzophenone 
• 1140-14-3 2,4-Dimethyl benzophenone 
• 84-54-8 2-methylanthracene-9,10-dione 
• 85-55-2 2-(4-toluoyl)benzoic acid 
• 28122-28-3 1-benzyl-2,4-dimethyl-benzene 
• 50259-89-7 2-Methyl-10H-anthracen-9-one 
• 514-10-3 abietic acid 
• 67135-97-1 (2,4-dimethylphenyl)(phenyl)methanol 
• 858277-53-9 1,4-dihydroxy-5-methylanthracene-9,10-dione 
• 96945-59-4 1,4-bis-(2,4-dimethyl-benzoyl)-benzene 
• 860602-78-4 1,2-bis-(2,5-dimethyl-benzoyl)-benzene 

Downstream Products

• 84-54-8 2-methylanthracene-9,10-dione 
• 117-78-2 anthraquinone-2-carboxylic acid 
• 177839-45-1 9,10-dibromo-2-methyl-anthracene 
• 23802-36-0 trans-2-<4-Phenyl-styryl>-anthracen 
• 78405-80-8 trans-2-(4-Isopropyl-styryl)-anthracen 
• 23802-70-2 trans-2-(3,4,5-Trimethoxy-styryl)-anthracen 
• 23802-69-9 trans-2-<3,4-Dimethoxy-styryl>-anthracen 
• 23802-71-3 trans-2-<4-Phenoxy-styryl>-anthracen 
• 23802-67-7 trans-2-(4-Chlor-styryl)-anthracen 
• 34086-37-8 C₃₁H₂₄O₂ 
• 804560-00-7 2-methyl-9,10-bis(naphthalen-2-yl)anthracene 
• 602-69-7 anthraquinone-1-carboxylic acid 
• 78405-79-5 trans-1-(2-anthryl)-2-phenylethene 

Relevant academic research and scientific papers

Palladium-catalyzed benzylic C(sp3)–H arylation of o-alkylbenzaldehydes

The palladium-catalyzed benzylic C(sp3)–H arylation of o-alkylbenzaldehyde derivatives was achieved utilizing 2-dimethylaminoethylamine as a novel transient directing group. The γ-C(sp3)–H arylation reaction efficiently afforded a variety of arylated o-alkylbenzaldehydes and polycyclic aromatic hydrocarbons (PAHs) in one pot, exhibiting high functional group tolerance with broad substrate scope. The aliphatic diamine auxiliary represents a simple, inexpensive, readily available, and removable directing group for C–H activation. The resultant o-benzylbenzaldehyde products could be diversely transformed into potentially important synthetic intermediates under mild conditions.

Preliminary investigations on the catalytic hydrogenation of polycyclic aromatic hydrocarbons via WGSR

The water-gas shift reaction (WGSR) is a crucial reaction in the direct liquefaction of lignite in a syngas (CO + H2) system. In this study, anthracene was utilized as a polycyclic model compound of lignite, to which hydrogen is donated by the H2/D2 produced from CO and H2O/D2O via the WGSR. The results show that the model compound of the polycyclic aromatic hydrocarbon in coal (anthracene) undergoes partial cracking and polycondensation under non-hydrogen-donor conditions at 400 °C. In addition, WGSR catalyzed by NiO can generate hydrogen for the hydrogenation of anthracene. Comparing the mass spectra of deuterated products with those of conventional hydrogenation products by isotope labeling, the alkyl side chain positions of toluene, 1,4-xylene, methylnaphthalene, 1,1-diphenylethylene, methylanthracene and other compounds are prone to deuteration, enabling speculation of the main hydrogenation route of anthracene, which provides theoretical support for the catalytic hydrogenation in direct liquefaction of lignite in a syngas (CO + H2) system.

A Remarkable Fluorescence Quenching Based Amplification in ATP Detection through Signal Transduction in Self-Assembled Multivalent Aggregates

Signal transduction is essential for the survival of living organisms, because it allows them to respond to the changes in external environments. In artificial systems, signal transduction has been exploited for the highly sensitive detection of analytes. Herein, a remarkable signal transduction, upon ATP binding, in the multivalent fibrillar nanoaggregates of anthracene conjugated imidazolium receptors is reported. The aggregates of one particular amphiphilic receptor sensed ATP in high pm concentrations with one ATP molecule essentially quenching the emission of thousands of receptors. A cooperative merging of the multivalent binding and signal transduction led to this superquenching and translated to an outstanding enhancement of more than a millionfold in the sensitivity of ATP detection by the nanoaggregates; in comparison to the “molecular” imidazolium receptors. Furthermore, an exceptional selectivity to ATP over other nucleotides was demonstrated.

Cascade reaction for the synthesis of polycyclic aromatic hydrocarbons via transient directing group strategy

A Pd(II)-catalyzed cascade synthesis of diverse polycyclic aromatic hydrocarbons via transient directing group strategy has been developed, involving the consecutive arylation, cyclization and aromatization. The efficiency and practicality were demonstrated by wide substrate range, concise synthetic pathway and mild reaction conditions. The subsequent transformations of the benz[a]anthracene core accessed natural bioactive PAH molecules.

Direct synthesis of anthracenes from o-tolualdehydes and aryl iodides through Pd(II)-Catalyzed sp3 C–H arylation and electrophilic aromatic cyclization

The first direct synthesis of substituted anthracenes from o-tolualdehydes and aryl iodides via a Pd(II)-catalyzed C–H arylation using an alcohol-bearing transient directing group and subsequent AgOTf-assisted electrophilic aromatic cyclization is described. New transient directing groups consisting of amino acids and amino alcohols enhanced the reactivity, and the C–H arylation was complete in 12 h at 90 °C. By simply changing the silver salt to silver triflate, the one-pot synthesis of anthracene derivatives was carried out using the present reaction conditions.

Decarbonylative Methylation of Aromatic Esters by a Nickel Catalyst

A Ni-catalyzed decarbonylative methylation of aromatic esters was achieved using methylaluminums as methylating agents. Dimethylaluminum chlorides uniquely worked as the methyl source. Because of the Lewis acidity of aluminum reagents, less reactive alkyl esters could also undergo the present methylation. By controlling the Lewis acidity of aluminum reagents, a chemoselective decarbonylative cross-coupling between alkyl esters and phenyl esters was successful.

Facile Synthesis of Polycyclic Aromatic Hydrocarbons: Br?nsted Acid Catalyzed Dehydrative Cycloaromatization of Carbonyl Compounds in 1,1,1,3,3,3-Hexafluoropropan-2-ol

The cycloaromatization of aromatic aldehydes and ketones was readily achieved by using a Br?nsted acid catalyst in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP). In the presence of a catalytic amount of trifluoromethanesulfonic acid, biaryl-2-ylacetaldehydes and 2-benzylbenzaldehydes underwent sequential intramolecular cationic cyclization and dehydration to afford phenacenes and acenes, respectively. Furthermore, biaryl-2-ylacetaldehydes bearing a cyclopentene moiety at the α-position underwent unprecedented cycloaromatization including ring expansion to afford triphenylenes. HFIP effectively promoted the cyclizations by suppressing side reactions presumably as a result of stabilization of the cationic intermediates.

Synthesis of annulated arenes and heteroarenes by hydriodic acid and red phosphorus mediated reductive cyclization of 2-(Hetero)aroylbenzoic acids or 3-(Hetero)arylphthalides

Annulated arenes and hetarenes were prepared in good to very good yields by hydriodic acid/red phosphorus mediated reductive cyclization of 3-(hetero)aryl phthalides. The reductive cyclization also proceeded successfully with 2-aroylbenzoic acids and 2-aroylnaphthoic acids.

Nickel-catalyzed cross-coupling of aryl or 2-menaphthyl quaternary ammonium triflates with organoaluminum reagents

The cross-coupling of aryltrimethylammonium triflates with AlMe3 and β-H-containing trialkylaluminums was performed in dioxane at 110 °C under catalysis of (dppp)NiCl2 to afford alkylated arenes. The cross-coupling of 2-menaphthyltri

Synthesis and characterization of highly soluble blue emitting poly(2-vinylanthracene) with 9,10-di(2-naphthalenyl) and 9,10-di(3-quinolinyl) substituents

Two new blue fluorescent polymers poly(910-di(2-naphthalenyl)-2- vinylanthracene) (P(2ADN)) and poly(9,10-di(3-quinolinyl)-2-vinylanthracene) (P(3ADQ)), were polymerized from free radical solution addition polymerization with Mn = 21,500 and 15,400, respectively. The polymers are highly soluble in common organic solvents while P(3ADQ) is also soluble in polar solvents including a 1/1 mixture of ethanol/water. Both polymers are amorphous with excellent thermal stability (Tg (Midpoint) = 343 C and 298 C for P(2ADN) and P(3ADQ), respectively). P(2ADN) exhibited three prominent absorption bands in tetrahydrofuran (364, 383 and 403 nm) and is similar to that of P(3ADQ) (369, 384 and 404 nm). The solid-state Commission Internationale d'Eclairage (CIEx,y) color coordinates for illumination were (0.15, 0.10) for P(2ADN) and (0.15, 0.13) for P(3ADQ) which lied within the requirements for a true blue display color. The photoluminescence (PL) of the polymers red-shifted 16-17 nm from their respective pendant chromophore 2-methyl-9,10-di(2-naphthalenyl)anthracene (2MADN) and 2-methyl-9,10-di(3- quinolinyl)anthracene (3MADQ) and can be attributed to partial π-π stacking between the adjacent aromatic pendant groups in the polymer chains. The luminescences of 3MADQ and P(3ADQ) are sensitive to pH and the pKa for the alkalescent 3MADQ and P(3ADQ) calculated was 2.4 and 2.7, respectively. Both polymers have similar band-gap energy (Eg) between 2.88 and 2.91 eV, while the LUMO/HOMO for P(3ADQ) is shifted slightly downward -0.06 to -0.03 eV compared to P(2ADN). The mobility (μhole) of the two polymers were measured to be 4.0 × 10-7 and 10-8 cm 2/(V-s) for P(2ADN) and P(3ADQ), respectively.