38313-16-5

Usage

Uses

Used in Chemical Synthesis:
1,8-Dibromo-9,10-anthraquinone is used as a reactant for electron-transfer reactions, which are crucial in the development of new materials and compounds with specific properties. Its ability to participate in electron-transfer reactions makes it a valuable component in the synthesis of various chemical products.
Used in Polymer Synthesis:
1,8-Dibromo-9,10-anthraquinone is used as a reactant in the synthesis of ferrocene-quinone conjugated oligomers and polymers. These conjugated systems have potential applications in the development of advanced materials with unique electronic, optical, and catalytic properties. The incorporation of anthraquinone into these polymers can enhance their performance in various applications, such as in sensors, energy storage, and catalysis.

Upstream product

• 82-48-4 1,8-anthraquinonedisulphonic acid 
• 82-43-9 1,8-dichloroanthraquinone 
• 82-49-5 1-anthraquinonesulfonic acid 
• 84-65-1 9,10-phenanthrenequinone 
• 117-14-6 1,5-anthraquinone disulfonate 
• 129-42-0 1,8-diamino-anthraquinone 

Downstream Products

• 60316-43-0 1,8-bis-methylaminoanthraquinone 
• 4981-66-2 9,10-Dihydroxyanthracene 
• 131276-24-9 1,8-dibromoanthraquinone 
• 63722-52-1 1,8-Dibrom-9-phenylanthracen 
• 1415609-79-8 1,8-Am₂Aq 
• 1415609-80-1 1,8-BrAmAq 

Relevant academic research and scientific papers

Extend Hypervalent 5c-6e Interactions: Linear Alignment of Five C-Se- - -O- - -Se-C Atoms in Anthraquinone and 9-Methoxyanthracene Bearing Arylselanyl Groups at the 1,8-Positions

The structures of 1,8-bis(phenylselanyl)anthraquinone (1a), 1,8-bis(phenylselanyl)-9-methoxyan-thracene (2a), and 1,8-bis(phenylselanyl)anthracene (3a) are determined by X-ray crystallographic analysis, together with the derivatives. The Se-Ci

Synthesis of a new tridentate anthracene ligand bearing (i-Pr)2P group at 1,8-positions: Facile bond switch on tetracoordinate boron atom

9-Borylanthracene 12 was prepared from 1,8-bis(diisopropyl-phosphino)-9-bromoanthracene (5) and the X-ray structure of 12 shows a tetrahedral boron atom coordinated by only one of the two (i-Pr)2P groups. However, anthracene protons were observ

First linear alignment of five C-Se...O...Se-C atoms in anthraquinone and 9-(methoxy)anthracene bearing phenylselanyl groups at 1,8-positions

Five Ci-Se...O...Se-Ci atoms in anthraquinone and 9-(methoxy)anthracene bearing phenylselanyl groups at 1,8-positions align linearly, the origin of which is shown to be a non-bonded 5c-6e interaction of the five atoms.

Synthesis, structure and anion binding properties of 1,8-bis(dimesitylboryl)anthracene and its monoborylated analog

Two boranes, 1-(dimesitylboryl)anthracene (1) and 1,8-bis(dimesitylboryl)anthracene (2), have been synthesized with the spectrophysical properties showing how the inclusion of one or two boron atoms progressively perturbs the π-system of the anthracene backbone. This perturbation is caused by conjugation of the anthracene-π? orbital with the vacant p-orbital on boron. Additionally, both 1 and 2 have a high affinity for fluoride and cyanide anions which are complexed in a 1:1 guest-host ratio. The mono-borane 1 is particularly well-suited for cyanide binding, displaying a binding constant of 3 × 107 in THF. Furthermore, as a result of their unique electronic structures, these boranes display a fluorescence response to fluoride anion characterized by a blue shift in the case of 1 and a red shift in the case of 2.

Enantioselective preparation and structural and conformational analysis of the chiral solvating agent α,α′-bis(trifluoromethyl)-1,8- anthracenedimethanol

The preparation of the enantiomers of α,α′- bis(trifluoromethyl)-1,8-anthracenedimethanol is described, and their conformational behaviour studied. These enantiomers are very active when used as chiral solvating agents in the presence of several compounds.

Syntheses and structures of hypervalent pentacoordinate carbon and boron compounds bearing an anthracene skeleton - Elucidation of hypervalent interaction based on X-ray analysis and DFT calculation

Pentacoordinate and tetracoordinate carbon and boron compounds (27, 38, 50-52, 56-61) bearing an anthracene skeleton with two oxygen or nitrogen atoms at the 1,8-positions were synthesized by the use of four newly synthesized tridentate ligand precursors. Several carbon and boron compounds were characterized by X-ray crystallographic analysis, showing that compounds 27, 56-59 bearing an oxygen-donating anthracene skeleton had a trigonal bipyramidal (TBP) pentacoordinate structure with relatively long apical distances (ca. 2.38-2.46 A). Despite the relatively long apical distances, DFT calculation of carbon species 27 and boron species 56 and experimental accurate X-ray electron density distribution analysis of 56 supported the existence of the apical hypervalent bond even though the nature of the hypervalent interaction between the central carbon (or boron) and the donating oxygen atom was relatively weak and ionic. On the other hand, X-ray analysis of compounds 50-52 bearing a nitrogen-donating anthracene skeleton showed unsymmetrical tetracoordinate carbon or boron atom with coordination by only one of the two nitrogen-donating groups. It is interesting to note that, with an oxygen-donating skeleton, the compound 61 having two chlorine atoms on the central boron atom showed a tetracoordinate structure, although the corresponding compound 60 with two fluorine atoms showed a pentacoordinate structure. The B-O distances (av 2.29 A) in 60 were relatively short in comparison with those (av 2.44 A) in 59 having two methoxy groups on the central boron atom, indicating that the B-O interaction became stronger due to the electron-withdrawing nature of the fluorine atoms.

Synthesis of a novel potential tridentate anthracene ligand, 1,8-bis(dimethylamino)-9-bromoanthracene, and its application as chelate ligand for synthesis of the corresponding boron and palladium compounds

A novel potential tridentate ligand, 1,8-bis(dimethylamino)-9-bromoanthracene, was synthesized. The key steps are as follows: 1) dimethylamination of 1,8-dibromo-9-methoxyanthracene by a modified Buchwald's method to afford 1,8-bis(dimethylamino)-9-methoxyanthracene, and 2) reduction of the methoxy group by LDBB (lithium di-tert-butylbiphenylide) followed by treatment with BrCF2CF2Br. The corresponding 1,8-bis(dimethylamino)-9-lithioanthracene, which should be a useful versatile tridentate ligand, could be generated by treatment of the bromide with one equivalent of nBuLi. The lithioanthracene reacted with B-chloroborane derivatives to give three 9-boryl derivatives. Although we recently reported that the crystal structure of 1,8-dimethoxy-9-B-catecholateborylanthracene was a symmetrical compound with the almost identical two O-B distances (2.379(2) and 2.441(2) A), the newly prepared 1,8-bis(dimethylamino)-9-borylanthracene derivatives clearly have unsymmetrical structures with coordination of only one NMe2 group toward the central boron atom. However, the energy difference between the unsymmetrical and symmeterical structures was found to be very small based on 1H NMR measurements, in which symmetrical anthracene patterns in the aromatic region (two kinds of doublets and a triplet) and a sharp singlet signal of the two NMe2 groups were observed even at - 80°C. 1,8-Bis(dimethylamino)-9-bromoanthracene itself can be a versatile ligand for transition metal compounds. In fact, direct palladation of the bromide took place by the reaction with [Pd2(dba)3]·CHCl3 in THF to give the 9-palladated product. x-ray crystallographic analysis of the Pd compound showed that the square planar palladium atom was coordinated in a symmetrical fashion by both NMe2 groups (Pd-N bonds are 2.138(5) and 2.146(5) A).

Triazinyl dyes

Vat dyestuffs of the formula EQU1 wherein R represents alkyl with 1 to 4 carbon atoms, R1 and R2 represent hydrogen or alkyl with 1 to 4 carbon atoms and each of A1 and A2 represents a vattable radical with 3 to 7 condensed rings are characterized by improved resistance to alkali and are suitable for dyeing and printing the most diverse materials, in particular fibers made from natural or regenerated cellulose.