613-31-0

Basic information

• Product Name: 9,10-DIHYDROANTHRACENE
• Synonyms: 9,10-Dihydroanthracene,90%,tech.;9.10-Dihydroanthracene 1g [613-31-0];Anthracene, dihydro-;9,10-DIHYDROANTHRACENE, TECH., 85%;9,10-DIHYDROANTHRACENE OEKANAL;6-Methoxy-1-Tetralone99%;9,10-Dihydroanthracene,99%;9,10-DIHYDROANTHRACENE, TECHN. 90%
• CAS NO: 613-31-0
• Molecular Formula: C₁₄H₁₂
• Molecular Weight: 180.25
• EINECS: 210-336-1
• Product Categories: Building Blocks;Organic Building Blocks;Arenes
• Mol File: 613-31-0.mol
• Article Data: 164

Chemical Properties

• Melting Point: 103-107 °C(lit.)
• Boiling Point: 312 °C(lit.)
• Flash Point: 131.8 °C
• Appearance: brown crystals
• Density: 0.88 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00152mmHg at 25°C
• Refractive Index: 1.6415 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: 1.332mg/L(24.59 oC)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• BRN: 1364575
• CAS DataBase Reference: 9,10-DIHYDROANTHRACENE(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-DIHYDROANTHRACENE(613-31-0)
• EPA Substance Registry System: 9,10-DIHYDROANTHRACENE(613-31-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36/37-26
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 613-31-0(Hazardous Substances Data)

Usage

Description

9,10-Dihydroanthracene (DHA) is an organic compound with the chemical formula C14H14 and is a derivative of anthracene. It is characterized by its brown crystalline appearance and is known for its chemical reactivity, particularly in hydrogenation and oxidation reactions.

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

• 85-52-9 2-Benzoylbenzoic acid 
• 50688-77-2 9-benzoyl-9,10-dihydroanthracene 
• 1564-53-0 9-benzoylanthracene 
• 84-65-1 9,10-phenanthrenequinone 
• 109-99-9 tetrahydrofuran 
• 18059-77-3 magnesium anthracene 
• 75-77-4 chloro-trimethyl-silane 
• 120-12-7 anthracene 
• 723-62-6 anthracen-9-carboxylic acid 
• 110-82-7 cyclohexane 
• 612-17-9 1,4-dihydronaphthalene 
• 519-73-3 triphenylmethane 
• 434-84-4 bianthronyl 
• 14314-91-1 9,10-dihydro-9-anthryl 

Downstream Products

• 192-97-2 benzo[e]pyrene 
• 120-12-7 anthracene 
• 41199-48-8 9-(p-toluoyl)-9,10-dihydroanthracene 
• 41199-47-7 (4-Chloro-phenyl)-(9,10-dihydro-anthracen-9-yl)-methanone 
• 41199-49-9 (9,10-Dihydro-anthracen-9-yl)-(2-fluoro-phenyl)-methanone 
• 14314-91-1 9,10-dihydro-9-anthryl 
• 98943-77-2 9-<2-(3,3-diphenylureido)ethyl>-9,10-dihydroanthracene 
• 98943-80-7 9,10-bis<2-(3,3-diphenylureido)ethyl>-9,10-dihydroanthracene 
• 50688-77-2 9-benzoyl-9,10-dihydroanthracene 
• 113893-59-7 N-(1-benzyl-2-chloro-2-phenethyl)benzamide 
• 1499-00-9 2-phenylaziridine 
• 3278-14-6 N-phenethylbenzamide 
• 22020-69-5 oxytriphine 
• 128600-81-7 9-(2-Benzamido-1-phenylethyl)-9,10-dihydroanthracene 

Relevant articles and documents

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.

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.

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.

Extremely Stable Anthraquinone Negolytes Synthesized from Common Precursors

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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.

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.