1074-24-4

Usage

Uses

Used in Chemical Synthesis:
1,4-Dibromo-2,5-dimethylbenzene is used as a chemical intermediate for the preparation of various organic compounds. It serves as a key building block in the synthesis of complex organic molecules and polymers.
Used in the Preparation of 4,4″-diformyl-2′,5′-dimethyl-1,1′,4′,1″-terphenyl:
1,4-Dibromo-2,5-dimethylbenzene is used as a starting material for the synthesis of 4,4″-diformyl-2′,5′-dimethyl-1,1′,4′,1″-terphenyl, which is an important compound in the production of specialty polymers and materials with unique properties.
Used in the Preparation of 1,4-diformyl-2,5-dimethylbenzene:
1,4-Dibromo-2,5-dimethylbenzene is also used in the preparation of 1,4-diformyl-2,5-dimethylbenzene, which is an intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and dyes.

InChI:InChI=1/C8H8Br2/c1-5-3-8(10)6(2)4-7(5)9/h3-4H,1-2H3

Upstream product

• 30273-40-6 4-bromo-2,5-dimethylaniline 
• 609-54-1 2,5-dimethylbenzenesulfonic acid 
• 106-42-3 para-xylene 
• 7553-56-2 iodine 
• 2050-44-4 N-(2,5-dimethylphenyl)acetamide 
• 13711-31-4 N-(4-bromo-2,5-dimethyl-phenyl)acetamide 

Downstream Products

• 3463-44-3 2,5-dibromo-3,6-dimethylnitrobenzene 
• 20871-01-6 2,5-dibromo-4-methylbenzoic acid 
• 36711-69-0 1,4-dibromo-2,5-bis(dibromomethyl)benzene 
• 105653-65-4 1,4-dibromo-2,5-bis-diacetoxymethyl-benzene 
• 35335-16-1 1,4-bis(bromomethyl)-2,5-dibromobenzene 
• 18870-10-5 2,5-Dibrom-p-toluylsaeurenitril 
• 63525-48-4 2,5-dibromoterephthalaldehyde 
• 18870-11-6 2,5-dibromobenzene-1,4-dinitrile 
• 90085-60-2 2,5-dimethyl-1,4-benzenediboronic acid 
• 30252-02-9 1,4-Bis-(chloromethyl)-2,5-dibromo-3,6-dimethylbenzol 
• 18087-56-4 2,5-Dibrom-3,6-dimethyl-benzylchlorid 
• 40642-06-6 C₆₆H₅₀O₂ 
• 78965-37-4 2,5-bis(2-hydroxyethyl)-1,4-dimethylbenzene 
• 75867-43-5 1,4-bis((trimethylsilyl)ethynyl)-2,5-dimethylbenzene 

Relevant academic research and scientific papers

Linear and V-shaped carbazole-based molecules functionalized by cyano acceptors and diversified donors: Synthesis, single- and two-photon related photophysical properties

A series of novel linear and V-shaped carbazole-based molecules functionalized by cyano acceptors and diversified donors (carbazole, diphenylamino, dimethylamino, methoxy, and ferrocene) were synthesized and characterized by hydrogen-1 nuclear magnetic resonance, carbon-13 nuclear magnetic resonance, Fourier transform infrared spectroscopy, and high-resolution mass spectrometry. Their linear and nonlinear optical properties including UV–visible absorption, single-photon excited fluorescence, two-photon absorption, and frequency up-converted fluorescence, were systematically investigated in various solvents. The time-resolved photoluminescence studies using time-correlated single photon counting revealed their fluorescence lifetimes in THF. The solvent polarity exerts little effect on their absorption properties, while the emission properties (maximum fluorescence wavelength, Stokes shift, fluorescence quantum yield) display solvent polarity dependencies. Donor-acceptor functionalities and molecular dimensionality are considered to be the crucial structural factors that influence their optical properties. Pumped by a femtosecond laser (690–990 nm, 80 MHz, 140 fs), all the target molecules emit intense frequency up-converted fluorescence except FC1 and FC2 which contain one or two ferrocene donors. The two-photon absorption cross-sections in THF are in the range of 631–3014 GM. The density functional theory calculations were also conducted to unravel their electronic structures and to further understand the structure-property relationships. To our knowledge, this study is the first to be concerned with the single- and two-photon related photophysical properties of these D-π-A-π-D′ and D′-π-A-π-D-π-A-π-D′ carbazole-based molecules (D = donor, A = acceptor, π = conjugated bridge).

A high efficiency pure organic room temperature phosphorescence polymer PPV derivative for OLED

For the purpose of improving device efficiency and reducing cost, it is necessary to develop pure organic molecules with room temperature phosphorescence (RTP). A high efficiency pure organic RTP polymer, poly-p-phenylene vinylene (PPV) derivative (Br-PPV-CHO), was designed and synthesized, which possesses a blue emission at 496 nm, an emission lifetime of 14.1 μs, and a photoluminescence quantum yield of 12.2%, and the HOMO and LUMO of ?5.35 eV and ?2.75 eV, respectively, showing a great potential application in the emitting layer of OLED. A device fabricated with the PPV derivative as the emitting material layer shows a max luminance of 194 cd/m2 when the Br-PPV-CHO content was 0.5 wt %, demonstrating the best RTP performance. The good properties of Br-PPV-CHO come from the substituent groups of bromine and aromatic aldehyde, and the molecular structure design strategy in the PPV derivative supplies a useful guidance for the design and syntheses of organic RTP materials.

A Series of Lanthanide Coordination Polymers Based on Designed Bifunctional 1,4-Bis(imidazol-1-yl)terephthalic Acid Ligand: Structural Diversities, Luminescence, and Magnetic Properties

On the basis of the designed bifunctional 1,4-bis(imidazol-1-yl)terephthalic acid (H2BTA) ligand, a series of three-dimensional lanthanide coordination polymers, namely, [La2(BTA)1.5(ox)1.5(H2O)3]n (1), [Nd(BTA)(ox)0.5(H2O)]n (2), {[Ln(HBTA)(ox)(H2O)]·xH2O}n (Ln = Pr for 3 (x = 0), Sm for 4 (x = 0), Dy for 5 (x = 1.5), and Eu for 6 (x = 1)), and [Ln(BTA)(SO4)0.5(H2O)]n (Ln = Eu for 7, and Tb for 8) were obtained with the help of oxalate or sulfate ions. On the basis of the binuclear La2 secondary building unit (SBUs), the framework of 1 displays an unprecedented (3,3,4,9)-connected net with the point symbol of (411.55.614.75.8)2(42.5)2(43)2(44.62). While in complex 2, the binuclear Nd2 SBUs are connected by the BTA2- ligands to generate an interestingly (4,10)-connected (412.516.612.75)(46)2 net. Complexes 3-6 are isomorphism and show a 2-fold interpenetrated 4-connected (66)-dia net. Complexes 7 and 8 are isomorphism and show a novel (4,5)-connected (44.62)(44.66) net. Photoluminescence investigations show that 2 is a good near-infrared luminescent material, and 4 is a rarely reported single component white light emitting material. Complexes 6 and 7 show typically red emission, while complex 8 shows typically green emission, which can be used as a red or green emitting phosphor. Moreover, the luminescent lifetimes and quantum yields of the titled complexes were investigated. The magnetic susceptibility data of 2 indicated there are antiferromagnetic interactions between the NdIII ions.

Rational design, facile synthesis, and linear/nonlinear optical properties of novel two-photon absorption stilbene derivatives with different configurations

Four novel two-photon absorption compounds (1MOBI, 2MOHA, 3BrBI, and 4BrHA), which have assembled stilbene π-bridge, different electron acceptors and donors, were synthesized conveniently via the one-step Horner-Wadsworth-Emmons reaction. Their configurations are A-π-D-π-A, D′-π-D-π-D′, A′-π-A-π-A′, and D-π-A-π-D, respectively. Their linear and nonlinear optical properties including linear absorption, one-photon excited fluorescence, two-photon absorption, and two-photon excited fluorescence, were systematically investigated in various solvents. The results demonstrate that the compounds with dihexylamino donors exhibit good optical properties. 2MOHA and 4BrHA exhibit large two-photon absorption cross-sections (2183 and 1737 GM) in DMF, which are larger than those of many known stilbene derivatives. The relationships between the structures and the optical properties were studied aided with the time-dependent density functional theory calculations.

Solid state multicolor emission in substitutional solid solutions of metal-organic frameworks

Preparing crystalline materials that produce tunable organic-based multicolor emission is a challenge due to the inherent inability to control the packing of organic molecules in the solid state. Utilizing multivariate, high-symmetry metal-organic frameworks, MOFs, as matrices for organic-based substitutional solid solutions allows for the incorporation of multiple fluorophores with different emission profiles into a single material. By combining nonfluorescent links with dilute mixtures of red, green, and blue fluorescent links, we prepared zirconia-Type MOFs and found that the bulk materials exhibit features of solution-like fluorescence. Our study found that MOFs with a fluorophore link concentration of around 1 mol % exhibit fluorescence with decreased inner filtering, demonstrated by changes in spectral profiles, increased quantum yields, and lifetime dynamics expected for excited-state proton-Transfer emitters. Our findings enabled us to prepare organic-based substitutional solid solutions with tunable chromaticity regulated only by the initial amounts of fluorophores. These materials emit multicolor and white light with high quantum yields (-2-14%), high color-rendering indices (>93), long shelf life, and superb hydrolytic stability at ambient conditions.

An N-heterocyclic carbene-functionalised covalent organic framework with atomically dispersed palladium for coupling reactions under mild conditions

Covalent organic frameworks (COFs) are a new class of crystalline porous materials that could function as excellent scaffolds for heterogeneous catalysts. Herein, we report a functionalised COF (COF-NHC) using N-heterocyclic carbene (NHC) as a monomer building block via a facile ionothermal strategy. The simple and easily prepared imine-linked COF-NHC possessed two coordination sites (NHC and amine), which could fix the active component (Pd) tightly in COF, leading to atomically dispersed Pd in a heterogeneous catalyst. The as-prepared Pd@COF-NHC showed high stability in the Suzuki-Miyaura coupling reaction of arylboronic acids and aryl halides in aqueous media at room temperature, and could be easily recycled and reused multiple times without the loss of catalytic activity. Moreover, C-C coupling reactions could be accomplished using triarylbismuth reagents in ethanol aqueous solutions with high yields.

Open-Chain Crown-Ether-Derived Two-Photon Fluorescence Probe for Real-Time Dynamic Biopsy of Mercury Ions

A novel two-photon fluorescence probe for Hg2+ derived from bis(styryl)terephthalonitrile, as a two-photon fluorophore, and bis[2-(2-hydroxyethyl sulfanyl) ethyl]amino group (ionophore), as a novel Hg2+ ligand, was developed. The probe possesses small molecule size, large two-photon absorption cross-section (1067 GM) in H2O, non-cytotoxic effect, long wavelength emission at 588nm, large Stokes shift (121nm), excellent photostability, high water solubility, good cell permeability, and pH insensitivity in the biologically relevant range. The probe can selectively detect Hg2+ ions in live cells and living tissues without interference from other metal ions and the membrane-bound probes, and its quenching constant is 8.73×105 M-1.

A two-photon fluorescent lipid raft probe derived from dicyanostilbene and similar to cholesterol’s structure

Lipid raft is a microdomain being rich in cholesterol and sphingolipid and closely related to neurodegenerative diseases such as Alzheimer’s disease and prion disease. Hence the study on the physiological mechanism of lipid raft is helpful to reveal its biological role and its correlations with diseases. Two-photon fluorescence probe for lipid raft is a sharp tool to achieve this goal. A dicyanocarbazolylstilbene-derived two-photon fluorescence probe for lipid raft (DLR) was developed. Both DLR and lipid raft belong to D-π-A (donor-π-acceptor; π: C = C) type rigid planar molecule, and contain four fused carbon rings (one five-membered ring and three six-membered ring), and bear a long carbon chain (C8H17). The excellent comparability between the rigid plane of the probe molecule and the rigid lipid raft could significantly enhance the specific affinity to lipid rafts. DLR’s maximum emission wavelength increased with medium polarity while its fluorescence intensity (FI) augmented with viscosity, and FI in DPPC (dipalmitoylphosphatidylcholine) was 20 times higher than that in DOPC (dioleoylphosphatidylcholine). DLR’s fluorescence lifetime in DPPC was more than 2.2 times longer than that in DOPC. These indicate that DLR can distinguish DPPC from DOPC. Φδs of DLR in DPPC and DOPC were 1350 GM and 67 GM, respectively. DLR can image lipid raft distribution in cells and tissues. Graphic abstract: [Figure not available: see fulltext.]

Isoreticular Crystallization of Highly Porous Cubic Covalent Organic Cage Compounds**

Modular frameworks featuring well-defined pore structures in microscale domains establish tailor-made porous materials. For open molecular solids however, maintaining long-range order after desolvation is inherently challenging, since packing is usually governed by only a few supramolecular interactions. Here we report on two series of nanocubes obtained by co-condensation of two different hexahydroxy tribenzotriquinacenes (TBTQs) and benzene-1,4-diboronic acids (BDBAs) with varying linear alkyl chains in 2,5-position. n-Butyl groups at the apical position of the TBTQ vertices yielded soluble model compounds, which were analyzed by mass spectrometry and NMR spectroscopy. In contrast, methyl-substituted cages spontaneously crystallized as isostructural and highly porous solids with BET surface areas and pore volumes of up to 3426 m2 g?1 and 1.84 cm3 g?1. Single crystal X-ray diffraction and sorption measurements revealed an intricate cubic arrangement of alternating micro- and mesopores in the range of 0.97–2.2 nm that are fine-tuned by the alkyl substituents at the BDBA linker.

Synthesis and structure of the bimetallic organoantimony catalyst and its application in diastereoselective direct Mannich reaction as facile separation catalytic system

A bimetallic organoantimony catalyst with four Lewis/Br?nsted acidic/basic sites assembled orderly was successfully synthesized and showed high catalytic efficiency. It has been applied in diastereoselective direct Mannich reaction by adding 0.1 mol% catalyst. This reaction presented unexpected facile separation ability from homogenous solution to heterogeneous solution.