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Usage

Uses

Used in Chemical Research:
9,10-Dihydroanthracene is used as a reactant in chemical studies, specifically for assessing the hydrogen abstraction capability of various complexes. In one study, it was used to evaluate the interaction with a valence-delocalized iron complex in MeCN (acetonitrile).
Used in Hydrogenation Processes:
DHA is utilized in the transfer hydrogenation of fullerenes, such as C60 and C70, in the presence of a [7H]benzanthrene catalyst. This process is significant for the synthesis of novel compounds and the study of their properties.
Used in Oxidation Reactions:
9,10-Dihydroanthracene is also used in oxidation reactions, where it can be oxidatively aromatized to the corresponding anthracene using molecular oxygen as an oxidant and activated carbon as a promoter in xylene. This transformation is important for the production of various anthracene-based compounds with potential applications in different industries.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, DHA may have potential applications in the pharmaceutical industry due to its chemical reactivity and ability to form complexes with other molecules. Further research could explore its use in drug development or as an intermediate in the synthesis of pharmaceutical compounds.
Used in Material Science:
The unique chemical properties of 9,10-dihydroanthracene may also find applications in material science, particularly in the development of new materials with specific optical, electronic, or structural properties. Its ability to participate in hydrogenation and oxidation reactions could be exploited to create novel materials with tailored characteristics for various applications.

Purification Methods

Crystallise it from EtOH [Rabideau et al. J Am Chem Soc 108 8130 1986]. [Beilstein 5 H 641, 5 IV 2182.]

InChI:InChI=1/C14H12/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1/h1-8H,9-10H2

Upstream product

• 120-12-7 anthracene 
• 90-44-8 anthracen-9(10H)-one 
• 1788-04-1 2-benzoylanthracene 
• 50688-77-2 9-benzoyl-9,10-dihydroanthracene 
• 611-63-2 9,10-dihydroanthracen-9-ol 
• 84-65-1 9,10-phenanthrenequinone 
• 109-99-9 tetrahydrofuran 
• 18059-77-3 magnesium anthracene 
• 67-56-1 methanol 
• 143824-79-7 C₁₄H₁₂ 
• 256-81-5 suberene 
• 75-77-4 chloro-trimethyl-silane 
• 92-83-1 xanthene 
• 121-72-2 N,N-dimethyl-m-toluidine 

Downstream Products

• 120-12-7 anthracene 
• 50688-77-2 9-benzoyl-9,10-dihydroanthracene 
• 41199-51-3 (9,10-Dihydro-anthracen-9-yl)-(4-ethoxy-phenyl)-methanone 
• 24269-10-1 9,9,10,10-tetramethyl-9,10-dihydroanthracene 
• 5910-28-1 1,4,5,8,9,10-hexahydroanthracene 
• 41199-47-7 (4-Chloro-phenyl)-(9,10-dihydro-anthracen-9-yl)-methanone 
• 41199-50-2 (9,10-Dihydro-anthracen-9-yl)-(4-methoxy-phenyl)-methanone 
• 41199-52-4 (4-Bromo-phenyl)-(9,10-dihydro-anthracen-9-yl)-methanone 
• 41199-49-9 (9,10-Dihydro-anthracen-9-yl)-(2-fluoro-phenyl)-methanone 
• 60-12-8 2-phenylethanol 
• 124465-83-4 9-(2-hydroxy-2-phenylethyl)-9,10-dihydroanthracene 
• 124465-84-5 9-(2-hydroxy-1-phenylethyl)-9,10-dihydroanthracene 
• 124465-88-9 9-(2-hydroxy-2-phenylethyl)-10-hydroxy-9,10-dihydroanthracene 
• 74851-74-4 [9]anthryl-benzyl sulfide 

Relevant academic research and scientific papers

Scanning Electrochemical Microscopy. 33. Application to the Study of ECE/DISP Reactions

The scanning electrochemical microscope (SECM) is used to measure the kinetics of ECE/DISP type reactions.The theory of the steady-state feedback response is developed in terms of numerical simulation.The theoretical curves show that the variation of the tip and substrate current with the tip-substrate separation can readily be used to differentiate between an ECE and a DISP1 pathway.The theoretical results suggest that rate constants up to 1.6E5 s-1 can be measured with tip sizes usually employed in SECM.The theory is validated using the experimental example of the reduction of anthracene in DMF in the presence of phenol.The reaction is shown to follow a DISP1 pathway, in agreement with previous studies.Good agreement is found between theory and experiment for all the phenol concentrations explored, and a rate constant of (4.4 +/- 0.4)E3 M-1 s-1 has been determined for the protonation of the anthracene radical anion by phenol.

Electron Transfer Catalysis of Arene Deco-ordination in the Cationic (η5-Cyclopentadienyl)(η6-arene)iron(II) Complexes

Replacement of the arene group in 5-C5H5)(η6-C6H6-nMen)>+ (n = 4) by three P(OMe)3 ligands is carried out under mild conditions by reductive electron transfer catalysis in acetonitrile and gives the free a

Tetra-anion of 9,9'-Bianthryl

9,9'-Bianthryl is reduced with lithium to yield a stable tetra-anion which can be characterised by n.m.r. spectroscopy and chemical evidence.

A novel Birch reduction of aromatic compounds using aqueous titanium trichloride: Anions of trans-10b,10c-dimethyl-2,7,10b,10c-tetrahydropyrene

The Birch reduction of 10b,10c-dimethyl-10b,10c-dihydropyrene 1 and anthracene could be predicted on the basis of their reduction potentials and achieved readily with aqueous titanium trichloride in near quantitative yields. Controlled reduction of a nitro group could be achieved under these conditions with the aromatic hydrocarbon remaining intact. The anion derived from the hexane obtained from reduction of 1 provided synthetic routes to derivatives of 1 inaccessible from direct substitution reactions of 1. Oxidative dimerization of the anion led to the formation of a series of interesting products.

Dimerization of cycloproparenes by silver ion

Cycloproparenes react with silver ion chloroform to yield dimers which can be aromatized by dichlorodicyanoquinone in benzene to give the corresponding acene.

Metal-free hydrogenation catalysis of polycyclic aromatic hydrocarbons

The frustrated Lewis pair, B(C6F5) 3/Ph2PC6F5, acts as an efficient catalyst for the hydrogenation of the polycyclic hydrocarbons including anthracene derivatives, tetracene and tetraphene, at 80 °C and 100 atm H2 pressure via a mechanism involving protonation of polyaromatic species followed by hydride transfer. The Royal Society of Chemistry.

Noble metal nanoparticles stabilized by hyper-cross-linked polystyrene as effective catalysts in hydrogenation of arenes

This work is addressing the arenes’ hydrogenation—the processes of high importance for petrochemical, chemical and pharmaceutical industries. Noble metal (Pd, Pt, Ru) nanoparticles (NPs) stabilized in hyper-cross-linked polystyrene (HPS) were shown to be active and selective catalysts in hydrogenation of a wide range of arenes (monocyclic, condensed, substituted, etc.) in a batch mode. HPS effectively stabilized metal NPs during hydrogenation in different medium (water, organic solvents) and allowed multiple catalyst reuses.

Visible light enables catalytic formation of weak chemical bonds with molecular hydrogen

The synthesis of weak chemical bonds at or near thermodynamic potential is a fundamental challenge in chemistry, with applications ranging from catalysis to biology to energy science. Proton-coupled electron transfer using molecular hydrogen is an attractive strategy for synthesizing weak element–hydrogen bonds, but the intrinsic thermodynamics presents a challenge for reactivity. Here we describe the direct photocatalytic synthesis of extremely weak element–hydrogen bonds of metal amido and metal imido complexes, as well as organic compounds with bond dissociation free energies as low as 31 kcal mol?1. Key to this approach is the bifunctional behaviour of the chromophoric iridium hydride photocatalyst. Activation of molecular hydrogen occurs in the ground state and the resulting iridium hydride harvests visible light to enable spontaneous formation of weak chemical bonds near thermodynamic potential with no by-products. Photophysical and mechanistic studies corroborate radical-based reaction pathways and highlight the uniqueness of this photodriven approach in promoting new catalytic chemistry. [Figure not available: see fulltext.].

Catalyzed transfer hydrogenation by 2-propanol for highly selective PAHs reduction

Catalytic hydrogenation of mono-, di- and trinuclear aromatic compounds has been studied under hydrogen transfer conditions at 150 °C and 82 °C in 2-PrOH as a hydrogen donor and with Raney nickel as a catalyst. In contrast to conjugated or condensed aromatic rings, isolated ones demonstrated low reactivity in transfer hydrogenation (TH) that can be used to increase the hydrogenation selectivity of the reaction. So, naphthalene and biphenyl are partially hydrogenated into tetralin and cyclohexylbenzene, respectively, with excellent conversion (≥ 96 %) and selectivity (≥ 98 %) for 5–6 h at 82 °C. Increasing the reaction temperature to 150 °C results expectedly in the hydrogenation of second aromatic ring, which occurs slowly enough. Only 8 % of decaline and 42 % of dicyclohexyl, correspondingly, were obtained after 5 h at 150 °C. At the same time, TH of trinuclear anthracene and phenanthrene at 150 °C resulted in the formation of deeper hydrogenated octahydro-anthracenes and -phenanthrenes, respectively.

A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions

A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.