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 
• 120-12-7 anthracene 
• 90-44-8 anthracen-9(10H)-one 
• 1788-04-1 2-benzoylanthracene 
• 50688-77-2 9-benzoyl-9,10-dihydroanthracene 
• 1564-53-0 9-benzoylanthracene 
• 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 

Downstream Products

• 861306-21-0 2-(9,10-dioxo-9,10-dihydro-anthracene-2-carbonyl)-benzoic acid 
• 120-12-7 anthracene 
• 523-27-3 9,10-Dibromoanthracene 
• 725744-58-1 2,9,10-tribromo-anthracene 
• 2141-42-6 1,2,3,4-tetrahydroanthracene 
• 1079-71-6 1,2,3,4,5,6,7,8-octahydroanthracene 
• 19128-78-0 (4aR,8aR,9aS,10aS)-tetradecahydroanthracene 
• 84-65-1 9,10-phenanthrenequinone 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 50688-77-2 9-benzoyl-9,10-dihydroanthracene 
• 192-97-2 benzo[e]pyrene 
• 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 

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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Method for reducing carbonyl reduction to methylene under illumination

The invention belongs to the technical field of organic chemical synthesis. The method comprises the following steps: (1) mixing the carbonyl compound and the amine compound in a solvent, reacting 3 - 6 under the illumination of 380 - 456 nm, the reaction system is low in toxicity, high in atom utilization rate 12 - 24h. and production efficiency, safe and controllable in reaction process and capable of simplifying the operation in the preparation and production process. At the same time, the residue toxicity of the reaction is minimized, the pollution caused by the production process to the environment is reduced, and the steps and operations of removing residues after the reaction are simplified. In addition, the reactant feedstock is readily available. The reactant does not need additional modification before the reaction, can be directly used for preparing production, simplifies the operation steps, and shortens the reaction route. The production cost is obviously reduced.

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.].

Sodium-Promoted Borylation of Polycyclic Aromatic Hydrocarbons

Sodium dispersion promotes the reductive borylation of polycyclic aromatic hydrocarbons (PAHs) with MeOBpin. Anthracenes and phenanthrenes are converted to the corresponding dearomatized diborylated products. The reductive diborylation of naphthalene-based small π-systems yields similar yet unstable products that are oxidized into formal C-H borylation products with unique regioselectivity. Pyrene is converted to 1-borylpyrene without the addition of an oxidant. The latter two reactions represent a new route to useful borylated PAHs that rivals C-X borylation and catalytic C-H borylation.