10349-31-2

Basic information

• Product Name: 9,9'-Bianthracene, 9,9',10,10'-tetrahydro-
• CAS NO: 10349-31-2
• Molecular Formula: C28H22
• Molecular Weight: 358.483
• Mol File: 10349-31-2.mol

Chemical Properties

• CAS DataBase Reference: 9,9'-Bianthracene, 9,9',10,10'-tetrahydro-(CAS DataBase Reference)
• NIST Chemistry Reference: 9,9'-Bianthracene, 9,9',10,10'-tetrahydro-(10349-31-2)
• EPA Substance Registry System: 9,9'-Bianthracene, 9,9',10,10'-tetrahydro-(10349-31-2)

Safety Data

• Hazardous Substances Data: 10349-31-2(Hazardous Substances Data)

Upstream product

• 613-31-0 9,10-dihydroanthracene 
• 10409-54-8 2-bromo-2-methyl-1-phenyl-propan-1-one 
• 7374-80-3 α,α,α',α'-tetramethyl-1,4-benzene dimethylchloride 
• 121-72-2 N,N-dimethyl-m-toluidine 
• 120-12-7 anthracene 
• 124-38-9 carbon dioxide 
• 766-04-1 benzyllithium 
• 14314-91-1 9,10-dihydro-9-anthryl 
• 121-69-7 N,N-dimethyl-aniline 
• 109-89-7 diethylamine 
• 124-40-3 dimethyl amine 

Downstream Products

• 613-31-0 9,10-dihydroanthracene 
• 120-12-7 anthracene 
• 523-27-3 9,10-Dibromoanthracene 

Relevant articles and documents

Iron(II) complexes supported by sulfonamido tripodal ligands: Endogenous versus exogenous substrate oxidation

High-valent iron species are known to act as powerful oxidants in both natural and synthetic systems. While biological enzymes have evolved to prevent self-oxidation by these highly reactive species, development of organic ligand frameworks that are capable of supporting a high-valent iron center remains a challenge in synthetic chemistry. We describe here the reactivity of an Fe(II) complex that is supported by a tripodal sulfonamide ligand with both dioxygen and an oxygen-atom transfer reagent, 4-methylmorpholine-N-oxide (NMO). An Fe(III)-hydroxide complex is obtained from reaction with dioxygen, while NMO gives an Fe(III)-alkoxide product resulting from activation of a C-H bond of the ligand. Inclusion of Ca2+ ions in the reaction with NMO prevented this ligand activation and resulted in isolation of an Fe(III)-hydroxide complex in which the Ca2+ ion is coordinated to the tripodal sulfonamide ligand and the hydroxo ligand. Modification of the ligand allowed the Fe(III)-hydroxide complex to be isolated from NMO in the absence of Ca2+ ions, and a C-H bond of an external substrate could be activated during the reaction. This study highlights the importance of robust ligand design in the development of synthetic catalysts that utilize a high-valent iron center. (Chemical Equation Presented).

Photochemical Reactions of Aromatic Compounds. XXXVI. The Photoreactions of Anthracene with Some Selected Tertiary Aromatic Amines in Polar Media

The photoreaction of anthracene witn N,N-dimethylaniline in acetonitrile gave 9-(p-dimethylaminophenyl)-9,10-dihydroanthracene in a good yield, along with 9,10-dihydroanthracene and 9,9',10,10'-tetrahydro-9,9'-bianthryl.This photoreaction was found to depend on the polarity of the solvent as well as on its protic or aprotic nature.With N,N-dimethyl-m-toluidine, a similar 1 : 1 adduct was obtained, while the reduced anthracenes were mainly formed in the photoreactions with N,N-dimethyl-o- and p-toluidines.The mechanisms were discussed in terms of the dissociation into the ion radical as well as their reactivities.

Arene Hydrides, 8. - SET vs. Nucleophilic Attack in Reactions of α-Bromoisobutyrophenone with Carbanions. Fragmentation of the Anion of Tetrahydrobianthracene

SET is the main reaction pathway between α-bromoisobutyrophenone (1) and the carbanions 7a-j- of diarylmethanes or disubstituted acetonitriles: 7- 7. + e and e + 1 Br- PhCOCMe2. (3).Main secon

Photochemical Reactions of Aromatic Compounds. Part 44. Mechanisms for Direct Photoamination of Arenes with Ammonia and Amines in the Presence of m-Dicyanobenzene

Mechanistic details of the efficient photoamination of arenes (ArH) with ammonia or aliphatic primary amines (RNH2) in the presence of m-dicyanobenzene (DCNB) in 9:1 acetonitrile-water have been analysed by kinetics.The initiation of the photoamination is electron transfer from excited singlet ArH to DCNB to generate the cation radical of ArH (ArH(1+*)), to which RNH2 undergoes nucleophilic addition.The rate constant (kN) for the nucleophilic addition to the phenanthrene cation radical depends on R, varying from 3E7 dm3 mol-1 s-1 for NH3 to 8.9E8 dm3 mol-1 s-1 for ButNH2.A plot of log kN versus the Taft ?* parameter is linear with a slope of -2.1, demonstrating a substantial positive charge on RNH2 in the transition state in line with the proposed mechanism.Photoamination withMe2NH is very inefficient for naphthalene, 2-methoxynaphthalene, and phenanthrene, and is attributed to electron exchange between ArH(1+*) and Me2NH being competitive with nucleophilic addition.Anthracene is efficiently photoaminated with Me2NH but inefficiently with Et2NH.Efficient photoamination requires that the observed oxidation potential of the amines is more positive by 0.3-0.4 eV than that of ArH.

Synthesis of Oligomeric Chains with 9,10-Dihydroanthracene Units by Carbanion Alkylation

Deprotonation of 9,10-dihydroanthracene (2) affords the monoanion 6 which is subjected to alkylation reactions with mono and bifunctional electrophiles.Crucial intermediates in syntheses using 6 are 9-(3-bromopropyl)-9,10-dihydroanthracene (7) and 1,3-bis(9,10-dihydro-9-anthryl)propane (9) since they provide access to linear oligomers in which 9,10-dihydroanthracene units are linked by trimethylene groups.The alkylation processes of these species can be extended to the structurally related polymer 4.The regio- and stereoselectivity of alkylation reactions are investigated by 1H- and 13C-NMR spectroscopy.

Reductive Photocarboxylation of Aromatic Hydrocarbons

Photoirradiation of aromatic hydrocarbons such as phenanthrene, anthracene, or pyrene in the presence of an amine and carbon dioxide in dipolar aprotic solvents resulted in reductive carboxylation of the hydrocarbon.The reaction was considered to proceed

Disproportionation-Recombination Rate Ratios for Hydroaromatic Radicals

Relative rates for radical disproportionation (R. + R'. RH + R'd) and recombination (R. + R'. RR') have been determined in the liquid phase at 150 deg C for a series of reactions involving resonance-stabilized hydroaromatic radicals.Self-reactions were studied for the 1-tetralyl, 1-indanyl, 9,10-dihydro-9-phenanthryl, and 9,10-dihydro-9-anthryl radicals.Four cross-radical reactions involving benzyl, diphenylmethyl, and 1-tetralyl radical as H-atom acceptors were also examined.Rate constant ratios (kd/kr) span the range of 1.34 for the self-reaction of 9,10- dihydro-9-phenanthryl radicals to 0.05 for the self-reaction of 9,10-dihydro-9-anthryl radicals.When disproportionation reaction exothermicity is sufficiently small, -ΔHd -1 (210 kJ mol-1), disproportionation rate constants decrease with decreasing exothermicity.A fit of liquid-phase data yields ln (kd/kr) per H atom = -10.1 - 0.163 ΔHd (kcal mol-1).

PHOTOREDUCTION OF AROMATIC COMPOUNDS VIA AMINE EXCIPLEXES

Many cata and peri condensed polynuclear aromatic compounds were reduced smoothly by sodium borohydride in absolute ethanol in the presence of a tertiary amine to give products in good yields.

THE ANIONIC ALKYLATION OF EASILY REDUCIBLE ARENES. A PHOTOCHEMICAL ROUTE TO NUCLEOPHILIC AROMATIC SUBSTITUTION OF ANTHRACENE BY ORGANOLITHIUMS

High yield nuclophilic addition ensues upon mixing tetrahydrofuran solutions of benzyllithium or cyclooctadienyllithium and anthracene at low temperatures.At least part of this addition proceeds by a single electron transfer pathway.Photolysis of the resulting adducts leads to the elimination of lithium hydride, giving net nucleophilic substitution in approximately 50percent yield.The analogous reaction fails with naphthalene, where photolysis of the organolithium/arene mixture leads to dimeric products derived from the organolithium.