781-43-1

Usage

Uses

Used in Pharmaceutical Industry:
9,10-Dimethylanthracene is used as an antioxidant-photosensitizer in dual-loaded polymeric micelles for controllable production of reactive oxygen species. This application is particularly relevant in the development of targeted drug delivery systems, where the controlled release of reactive oxygen species can enhance the therapeutic efficacy of certain treatments.
Used in Chemical Research:
9,10-Dimethylanthracene serves as a chemical rate constant actinometer in singlet molecular oxygen reactions. This role is crucial in studying the kinetics and mechanisms of photochemical reactions, as well as in the development of new photoactive materials and processes. Its use as an actinometer allows researchers to accurately measure the rate constants of reactions involving singlet oxygen, providing valuable insights into the underlying photochemical processes.

Synthesis Reference(s)

Journal of the American Chemical Society, 104, p. 5807, 1982 DOI: 10.1021/ja00385a052The Journal of Organic Chemistry, 53, p. 2120, 1988 DOI: 10.1021/jo00244a056

Health Hazard

9,10-DIMETHYLANTHRACENE caused lungs and skin tumorin mice at the site of application. Carcinogenicity in humans is unknown. It testedpositive in the histidine reversion–Amestest; the mammalian micronucleus test wasinconclusive.

Purification Methods

Purify 9,10-dimethylanthracene by crystallising from EtOH, and by recrystallising from the melt. [Beilstein 5 IV 2329.]

InChI:InChI=1/C16H14/c1-11-13-7-3-5-9-15(13)12(2)16-10-6-4-8-14(11)16/h3-10H,1-2H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 73653-01-7 10-methylanthrone 
• 612-00-0 1,1'-ethylidenebis-benzene 
• 100-41-4 ethylbenzene 
• 27998-91-0 10-methyl-9-(iodomethyl)anthracene 
• 1705-94-8 acetic acid 10-oxo-9,10-dihydro-anthracen-9-yl ester 
• 676-58-4 methylmagnesium chloride 
• 75-16-1 methylmagnesium bromide 
• 141-78-6 ethyl acetate 
• 71-43-2 benzene 
• 105-39-5 chloroacetic acid ethyl ester 
• 108-88-3 toluene 
• 74-86-2 acetylene 
• 109-94-4 formic acid ethyl ester 

Downstream Products

• 34373-96-1 9,10-dibromomethylanthracene 
• 10273-84-4 anthracene-9,10-diylbis(methyl) diacetate 
• 857589-52-7 9,10-dimethyl-9,10-ditrityl-9,10-dihydro-anthracene 
• 30122-21-5 C₁₉H₁₈ 
• 58696-04-1 12-(4-chloro-benzoyl)-9,10-dimethyl-9,10-dihydro-10,9-oxaazaethano-anthracene 
• 2202-74-6 C₂₆H₂₄O₂ 
• 65121-64-4 C₂₆H₂₁NO₂ 
• 51029-28-8 10-(1-oxoethyl)-9,10-dihydro-9,10-dimethyl-10,9-(epoxyimino)anthracene 
• 109-66-0 pentane 
• 7072-00-6 10-methyl-9-anthraldehyde 
• 71000-08-3 10-carboxaldehyde-9-anthracenecarboxylic acid 
• 117110-53-9 12-benzoyl-9,10-dihydro-9,10-dimethyl-10,9-(episelenomethano)anthracene 
• 135-59-1 7-Imino-7H-phenothiazin-3-ylamine 
• 80515-94-2 12<<1-(3,4-(dimethoxy)phenyl)cyclohex-2-enyl>acetyl>-9,10-dihydro-9,10-dimethyl-10,9-(epoxyimino)anthracene 

Relevant academic research and scientific papers

Synthesis of thioacrolein S-oxide and thioketene S-oxide using FVT

FVT was used to synthesize thioacrolein S-oxide and thioketene S-oxide. These reactive species were characterized at low temperature by IR and/or NMR spectroscopies.

Substituted 9-Anthraldehydes from Dibenzocycloheptanol Epoxides via Acid-Catalyzed Epoxide Opening/Semipinacol Rearrangement

Starting from benzaldehyde derivatives, the corresponding dibenzocycloheptenol could be prepared in five steps. Under both substrate (secondary vs tertiary alcohol and the substituents on the aromatic ring(s)) and condition control, the subsequent epoxidation and acid-catalyzed epoxide opening/semipinacol rearrangement/aromatization afforded the corresponding 9-anthraldehydes in good yields, up to 88% over two steps. The presence of the electron-withdrawing group(s) on the aromatic ring(s) suppressed the rate of the epoxidation while the subsequent semipinacol rearrangement step required heating; the presence of the electron-donating group(s), on the other hand, frequently led to the decomposition during the epoxidation. From the mechanistic studies, the semipinacol rearrangement of the epoxide could precede the ionization at the bisbenzylic position, yielding the aldehyde intermediate. The ensuing dehydrative aromatization led to the formation of 9-anthraldehyde. Conversely, nucleophilic addition to the aldehyde and dehydrative aromatization with concomitant loss of formic acid led to anthracene.

1,4-Dehydrogenation with a Two-Coordinate Cyclic (Alkyl)(amino)silylene

Cyclic (alkyl)(amino)silylene (CAASi) 1 has been found to successfully dehydrogenate 1,4-dihydroaromatic compounds containing various substituents to afford the corresponding aromatic compounds. The observed high substrate generality proves 1 to be a potential 1,4-dehydrogenation reagent for organic compounds. For the reaction with 9,10-dimethyl-9,10-dihydroanthracene, silylene 1 activated not only benzylic C?H bonds but also aromatic C?H bonds to yield a silaacenaphthene derivative, which is an unprecedented reaction of silylenes. The results of the experimental and computational study of the reaction of CAASi 1 with 9,10-dihydroanthracene and 1,4-cyclohexadiene are consistent with the notion that 1,4-dehydrogenation with CAASi 1 proceeds mainly through a stepwise hydrogen-abstraction mechanism.

Features of the Diels-Alder reaction between 9,10-diphenylanthracene and 4-phenyl-1,2,4-triazoline-3,5-dione

The Diels-Alder reaction between substituted anthracenes 1a-1j and 4-phenyl-1,2,4-triazoline-3,5 (2) is studied. In all cases except one, the reaction proceeds on the most active 9,10-atoms of substituted anthracenes. The orthogonality of the two phenyl groups at the 9,10-position of diene 1a is found to shield 9,10-reactive centers. No dienophiles with C=C bonds are shown to participate in the Diels-Alder reaction with 1a; however, the reaction 1a + 2 proceeds with the very active dienophile 2,4-phenyl-1,2,4-triazoline-3,5-dione. It is shown that attachment occurs on the less active but sterically accessible 1,4-reactive center of diene 1a. The structure of adduct 3a is proved by 1H and 13C NMR spectroscopy and X-ray diffraction analysis. The following parameters are obtained for reaction 1a + 2 ? 3a in toluene at 25°C: Keq = 2120 M-1, ΔHf≠ = 58.6 kJ/mol, ΔSf≠ = -97 J/(mol K), ΔVf≠ = -17.2 cm3/mol, ΔHb ≠ = 108.8 kJ/mol, ΔSb≠ = 7.3 J/(mol K), ΔVb≠ = -0.8 cm3/mol, ΔHr-n = -50.2 kJ/mol, ΔSr-n = -104.3 J/(mol K), ΔVr-n = -15.6 cm3/mol. It is concluded that the values of equilibrium constants of the reactions 1a-1j + 2 ? 3a-3j vary within 4 × 101-1011 M-1.

Cobalt-catalyzed branched-selective addition of aromatic ketimines to styrenes under room-temperature conditions

An improved cobalt-based catalytic system has been developed for the branched-selective addition of aromatic ketimines to styrenes. With an appropriate combination of triarylphosphine and the Grignard reagent, the reaction takes place smoothly at room temperature to afford 1,1-diarylethane derivatives with high regioselectivity.

Dynamic Covalent chemistry: A facile room-temperature, reversible, diels-alder reaction between anthracene derivatives and n-phenyltriazolinedione

A series of readily accessible, dynamic Diels-Alder reactions that are reversible at room temperature have been developed between anthracene derivatives as dienes and N-phenyl-1,2,4-triazoline-3,5-dione as the dienophile. The adducts formed undergo reversible component exchange to form dynamic libraries of equilibrating cycloadducts. Furthermore, reversible adduct formation allows temperature-dependent modulation of the fluorescent properties of anthracene components; a feature of potential interest for the design of optodynamic polymeric materials by careful selection and manipulation of these simple dienes and dienophiles. Copyright

Photogeneration and reactivity of acyl nitroso compounds

Acyl nitroso compounds have been generated by photolysis of several different classes of precursors including 9,10-dimethylanthracene adducts, nitrodiazo compounds, and 1,2,4-oxadiazole-4-oxides. Consideration of the nitronate-like resonance structure of nitrodiazo compounds led to an examination of the photochemistry of nitronates with -leaving groups. Photolysis of such nitronates has been shown to generate an acyl nitroso species along with a carbene intermediate. Nanosecond time-resolved infrared (TRIR) spectroscopy has been used to detect photogenerated acyl nitroso compounds directly and to examine their reaction kinetics with amines and thiols. The mechanism of acyl nitroso aminolysis by primary amines involves general base catalysis, while the mechanism of aminolysis by secondary amines is strictly bimolecular. Thiols do not seem to be reactive with acyl nitroso compounds on the microsecond time scale, but thiolates are quite reactive. The reaction between benzoyl nitroside and an organic-soluble thiolate, tetrabutylammonium dodecanethiolate, proceeds via a proposed tetrahedral intermediate, which is observable by TRIR spectroscopy.

Low temperature Kumada-Corriu cross-coupling of polychlorinated acene derivatives and a synthesis of sterically demanding acenes

Conditions for low-temperature Kumada-Corriu cross-coupling of polychlorinated acenes with Grignard reagents are reported. Our work was motivated by a search for cross-coupling reactions effective in the synthesis of functionalized linear acenes for organic materials applications. Treatment of polychlorinated acenes with the PEPPSI-IPr catalyst and MeMgBr undergo 6-8 concurrent coupling reactions to yield products such as octamethylnaphthalene, which is distorted out of planarity due to the steric interaction between the methyl groups. More sterically demanding Grignard reagents such as PhMgBr coupled cleanly with 9,10-dichloroanthracene to provide products such as 9,10-diphenylanthracene, a blue OLED component, in excellent yield.

X-ray structure of a CT complex relevant to Diels-Alder reactivity of anthracenes

(Chemical Equation Presented) Combining the results of thermodynamic and kinetic investigations with an X-ray characterization of a transient CT complex sheds more light on the Diels-Alder reactivity of a strongly electron-deficient olefin, namely the 4-n

Photoactivatable HNO-releasing compounds using the retro-Diels-Alder reaction

We synthesized hetero-Diels-Alder cycloadducts from acyl nitroso derivatives and 9,10-dimethylanthracene, to be photo-inducible HNO-releasing agents and found that introduction of conjugated nitroaromatic groups effectively enhanced the responsiveness of HNO release to UV-A irradiation; we confirmed photoinduced HNO formation by EPR and GCMS analysis. The Royal Society of Chemistry.