61592-89-0

Basic information

• Product Name: Benzene, 1,1'-methylenebis[2-bromo-
• Synonyms: Benzene, 1,1‘-methylenebis[2-bromo-;2,2'-dibrom-diphenylmethan;bis-(2-bromophenyl)methane;bis(2-bromophenyl)methane;Bis-(2-brom-phenyl)-methan;1,1'-methylenebis(2-bromo-benzene);bis-(2-bromo-phenyl)-methane
• CAS NO: 61592-89-0
• Molecular Formula: C13H10Br2
• Molecular Weight: 326.03
• Mol File: 61592-89-0.mol

Chemical Properties

• Boiling Point: 331.88°C (rough estimate)
• Density: 1.6197
• Refractive Index: 1.6300 (estimate)
• CAS DataBase Reference: Benzene, 1,1'-methylenebis[2-bromo-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,1'-methylenebis[2-bromo-(61592-89-0)
• EPA Substance Registry System: Benzene, 1,1'-methylenebis[2-bromo-(61592-89-0)

Safety Data

• Hazardous Substances Data: 61592-89-0(Hazardous Substances Data)

Upstream product

• 861525-32-8 bis-(5-amino-2-bromo-phenyl)-methane 
• 25187-01-3 2,2’-dibromobenzophenone 
• 123335-02-4 bis-(2-bromophenyl)methanol 
• 61592-98-1 1,2-bis(2-bromophenyl)-2-hydroxyethan-1-one 
• 6630-33-7 ortho-bromobenzaldehyde 
• 51417-57-3 1,2-Bis(2-bromophenyl)ethane-1,2-dione 
• 61592-99-2 2.2'-Dibrom-benzilsaeure 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 583-53-9 2,3-dibromobenzene 
• 583-55-1 1-Bromo-2-iodobenzene 

Downstream Products

• 7147-07-1 9-(2-Aminoaethoxy)-9,10-dihydro-9-boraanthracen 
• 1591669-01-0 1'-benzyl-2',3'-dihydro-1'H,10H-spiro[anthracene-9,4'-pyridine] 
• 24672-71-7 9-(4’-bromophenyl)anthracene 
• 713542-04-2 1,3,5-tri(anthracen-9-yl)benzene 
• 146746-37-4 9-(2'-hydroxyphenyl)anthracene 
• 1252763-38-4 2-(anthracen-9-yl)aniline 
• 23674-15-9 9-(p-methoxyphenyl)anthracene 
• 192373-35-6 (bis(2-(diphenylphosphino)phenyl)methane) 
• 86-73-7 9H-fluorene 
• 23708-66-9 5,5-dimethyl-5,10-dihydrodibenzo[b,e]stannine 
• 33586-37-7 9-mesityl-9,10-dihydro-9-boraanthracene 
• 42528-36-9 acridin-10(9H)-yl(phenyl)methanone 
• 1252763-55-5 10-benzyloxycarbonyl-9,10-dihydroacridine 

Relevant articles and documents

Methylene Bridging Effect on the Structures, Lewis Acidities and Optical Properties of Semi-planar Triarylboranes

Three synthetic methods towards semi-planar triarylboranes with two aryl rings connected by a methylene bridge have been developed. The fine-tuning of their stereoelectronic properties and Lewis acidities was achieved by introducing fluorine, methyl, methoxy, n-butyl and phenyl groups either at their exocyclic or bridged aryl rings. X-ray diffraction analysis and quantum-chemical calculations provided quantitative information on the structural distortion experienced by the near planar hydro-boraanthracene skeleton during the association with Lewis bases such as NH3 and F?. Though the methylene bridge between the ortho-positions of two aryl rings of triarylboranes decreased the Gibbs free energies of complexation with small Lewis bases by less than 5 kJ mol?1 relative to the classical Lewis acid BAr3, the steric shielding of the CH2 bridge is sufficient to avoid the formation of Lewis adducts with larger Lewis bases such as triarylphosphines. A newly synthesized spirocyclic amino-borane with a long intramolecular B?N bond that could be dissociated under thermal process, UV-irradiation, or acidic conditions might be a potential candidate in Lewis pairs catalysis.

Method for preparing organic carboxylic ester through combined catalysis of aryl bidentate phosphine ligand

The invention discloses a method for preparing organic carboxylic ester by combined catalysis of an aryl bidentate phosphine ligand. The method comprises the following steps: under the action of a palladium compound/aryl bidentate phosphine ligand/acidic additive combined catalyst, carrying out a hydrogen esterification reaction on terminal olefin, carbon monoxide and alcohol so as to generate theorganic carboxylic ester with one more carbon than olefin. According to the invention, by adoption of the palladium compound/aryl bidentate phosphine ligand/acidic additive combined catalyst, good catalytic activity and selectivity for the hydrogen esterification reaction of the olefin are achieved, and olefin carbonylation to synthesize organic carboxylic ester can be efficiently catalyzed. Thearyl bidentate phosphine ligand has a rigid skeleton structure of a rigid ligand and the flexibility of a flexible ligand, so the aryl bidentate phosphine ligand has proper flexibility due to the characteristic that the aryl bidentate phosphine ligand is soft and rigid, and a most favorable coordination mode and a stable active structure in space are favorably formed. In addition, the aryl bidentate phosphine ligand has the advantages of high stability, simple and convenient synthesis method and the like; and a novel industrial technology is provided for production of organic carboxylate compounds.

Fast Photochromism of the Imidazole Dimers Bridged by Group 14 Atoms

We developed fast photochromic imidazole dimers bridged by group 14 atoms. These compounds reversibly break the C-N bond to generate the colored open-ring biradical form. The colored form thermally reproduces the initial colorless form in the microsecond

Copper-Catalyzed N,N-Diarylation of Amides for the Construction of 9,10-Dihydroacridine Structure and Applications in the Synthesis of Diverse Nitrogen-Embedded Polyacenes

We reported herein CuI/DMEDA catalyzed N,N-diarylation reaction of amides with various di(o-bromoaryl)methanes to produce diverse 9,10-dihydroacridine derivatives. The resulting 9,10-dihydroacridine derivatives were oxidized selectively under mild conditions to afford acridine, acridinone, and acridinium derivatives. The copper-catalyzed N,N-diarylation reaction coupled with oxidative aromatization reaction enabled the facile construction of nitrogen atom-embedded tetracenes and pentacenes of different ortho-fused patterns. The luminescence properties, especially the effect of fusion pattern on fluorescence emission of acquired N-polycenes, were also demonstrated.

Au-catalyzed biaryl coupling to generate 5- to 9-membered rings: Turnover-limiting reductive elimination versus π-complexation

The intramolecular gold-catalyzed arylation of arenes by aryl-trimethylsilanes has been investigated from both mechanistic and preparative aspects. The reaction generates 5- to 9-membered rings, and of the 44 examples studied, 10 include a heteroatom (N, O). Tethering of the arene to the arylsilane provides not only a tool to probe the impact of the conformational flexibility of Ar-Au-Ar intermediates, via systematic modulation of the length of aryl-aryl linkage, but also the ability to arylate neutral and electron-poor arenes-substrates that do not react at all in the intermolecular process. Rendering the arylation intramolecular also results in phenomenologically simpler reaction kinetics, and overall these features have facilitated a detailed study of linear free energy relationships, kinetic isotope effects, and the first quantitative experimental data on the effects of aryl electron demand and conformational freedom on the rate of reductive elimination from diaryl-gold(III) species. The turnover-limiting step for the formation of a series of fluorene derivatives is sensitive to the reactivity of the arene and changes from reductive elimination to π-complexation for arenes bearing strongly electron-withdrawing substituents (σ > 0.43). Reductive elimination is accelerated by electron-donating substituents (ρ = -2.0) on one or both rings, with the individual σ-values being additive in nature. Longer and more flexible tethers between the two aryl rings result in faster reductive elimination from Ar-Au(X)-Ar and lead to the π-complexation of the arene by Ar-AuX2 becoming the turnover-limiting step.

Au-Catalyzed Biaryl Coupling to Generate 5- To 9-Membered Rings: Turnover-Limiting Reductive Elimination versus ?-Complexation

The intramolecular gold-catalyzed arylation of arenes by aryl-trimethylsilanes has been investigated from both mechanistic and preparative aspects. The reaction generates 5- to 9-membered rings, and of the 44 examples studied, 10 include a heteroatom (N, O). Tethering of the arene to the arylsilane provides not only a tool to probe the impact of the conformational flexibility of Ar-Au-Ar intermediates, via systematic modulation of the length of aryl-aryl linkage, but also the ability to arylate neutral and electron-poor arenes - substrates that do not react at all in the intermolecular process. Rendering the arylation intramolecular also results in phenomenologically simpler reaction kinetics, and overall these features have facilitated a detailed study of linear free energy relationships, kinetic isotope effects, and the first quantitative experimental data on the effects of aryl electron demand and conformational freedom on the rate of reductive elimination from diaryl-gold(III) species. The turnover-limiting step for the formation of a series of fluorene derivatives is sensitive to the reactivity of the arene and changes from reductive elimination to ?-complexation for arenes bearing strongly electron-withdrawing substituents (σ > 0.43). Reductive elimination is accelerated by electron-donating substituents (ρ = -2.0) on one or both rings, with the individual σ-values being additive in nature. Longer and more flexible tethers between the two aryl rings result in faster reductive elimination from Ar-Au(X)-Ar and lead to the ?-complexation of the arene by Ar-AuX2 becoming the turnover-limiting step.

Strongly Luminescent Cyclometalated Gold(III) Complexes Supported by Bidentate Ligands Displaying Intermolecular Interactions and Tunable Emission Energy

A series of charge-neutral AuIII complexes, which comprise a dicarbanionic C-deprotonated biphenyl ligand and bidentate ancillary ligands ([Au(C^C)(L^X)]; L^X=β-diketonate and relatives (O^O), quinolinolate and relatives (N^O), and diphosphino (P^P) ligands), were prepared. All the complexes are emissive in degassed CH2Cl2 solutions and in thin-film samples with Φem up to 18 and 35 %, respectively, except for 5 and 6, which bear (N^O)-type ancillary ligands. Variation of the electronic characteristics of the β-diketonate ancillary ligand was demonstrated to be a viable route for tuning the emission color from blue-green (peak λem at ca. 466 nm for 1 and 2; 501 nm for 4 a and 4 b) to orange (peak λem at 585 nm for 3), in contrast to the common observations that the ancillary ligand has a negligible effect on the excited-state energy of the AuIII complexes reported in the literature. DFT/time-dependent (TD) DFT calculations revealed that the energies of the 3ππ*(C^C) and the 3ILCT(O^O) excited states (ILCT=intraligand charge transfer) switch in order on going from O^O=acetylacetonate (acac) to aryl-substituted β-diketonate ligands. Solution-processed and vacuum-deposited organic light-emitting diode (OLED) devices of selected complexes were prepared. The vacuum-deposited OLED fabricated with 2 displays a sky-blue emission with a maximum external quantum efficiency (EQE) of 6.71 % and CIE coordinates of (0.22, 0.40). The crystal structures of 7 and 9 reveal short intermolecular AuIII???AuIII contacts, with intermetal distances of 3.408 and 3.453 ?, respectively. DFT/TDDFT calculations were performed on 7 and 9 to account for the noncovalent interactions. Solid samples of 1, 3, and 9 exhibit excimeric emission at room temperature, which is rarely reported in AuIII complexes.

Direct Transformation of Esters into Arenes with 1,5-Bifunctional Organomagnesium Reagents

A direct transformation of carboxylic acid esters into arenes with 1,5-bifunctional organomagnesium reagents is described. This efficient and practical method enables the one-step defunctionalization of various carboxylic acid esters to prepare benzene, anthracene, tetracene, and pentacene derivatives. A double nucleophilic addition of the 1,5-organodimagnesium reagent to the ester is followed by an immediate 1,4-elimination reaction that leads to the direct [5+1] formation of a new aromatic ring.

Pd-catalyzed autotandem C-C/C-C bond-forming reactions with tosylhydrazones: Synthesis of spirocycles with extended π-conjugation

A new Pd-catalyzed autotandem process is presented by the reaction of tosylhydrazones of cyclic ketones and 2,2′-dibromobiphenyls and related systems. The process involves cross-coupling with tosylhydrazone followed by an intramolecular Heck reaction and gives rise to spirocyclic structures. Noteworthy, two C-CAr bonds are formed on the hydrazonic carbon during the process. Depending on the starting dibromide, an array of spirofluorenes, spirodibenzofluorenes, spiroacridines, and spiroanthracenes have been prepared. Thus, this methodology may be applied for the preparation of interesting structures useful in the development of optoelectronic materials.

Synthesis and comparative characterization of 9-boraanthracene, 5-boranaphthacene, and 6-borapentacene stabilized by the H2IMes carbene

A general procedure for the preparation of three N-heterocyclic carbene stabilized, boron-containing acenes (9-boraanthracene, 5-boranaphthacene, and 6-borapentacene) is presented. The key steps involve a transmetallation reaction between BCl3 and an appropriate stannacyclic precursor, and the dehydrochlorination of the H2IMes adduct of the chloroborane product. Comparative structural, photophysical, and redox properties reveal narrow HOMO-LUMO gaps relative to the all-carbon acene analogues. Just add boron: Synthetic routes to the N-heterocyclic-carbene-stabilized 5-boranaphthacene and 6-borapentacene are described and complement that previously developed for 9-boraanthracene. Comparative structural, photophysical, and redox properties reveal narrow HOMO-LUMO gaps relative to the all-carbon acene analogues.