15442-91-8

Usage

Uses

Used in Synthesis of Tetrapodal Imidazolium Ligands:
1,2,4,5-Tetrakis(bromomethyl)benzene is used as a key intermediate for the synthesis of tetrapodal imidazolium ligands, particularly in their PF6? salts. These ligands are essential in the development of novel coordination complexes and have potential applications in catalysis and supramolecular chemistry.
Used in Synthesis of Conformationally Constrained Cyclic α-Amino Acid Derivatives:
In the pharmaceutical industry, 1,2,4,5-Tetrakis(bromomethyl)benzene is utilized as a starting material for the synthesis of conformationally constrained cyclic α-amino acid derivatives. These derivatives are valuable in the development of new drugs with improved bioavailability and selectivity.
Used in Synthesis of Dendrimeric Organoplatinum Complexes:
1,2,4,5-Tetrakis(bromomethyl)benzene is also employed in the synthesis of dendrimeric organoplatinum complexes. These complexes have potential applications in cancer therapy and as catalysts in various chemical reactions.
Used in Synthesis of Thiacyclophanes:
In the field of organic chemistry, 1,2,4,5-Tetrakis(bromomethyl)benzene is used as a precursor for the synthesis of thiacyclophanes. These compounds are of interest due to their unique structural properties and potential applications in materials science and supramolecular chemistry.

InChI:InChI=1/C10H10Br4/c11-3-7-1-8(4-12)10(6-14)2-9(7)5-13/h1-2H,3-6H2

Upstream product

• 35168-62-8 2,5-dibromomethyl-p-xylene 
• 106-42-3 para-xylene 
• 95-93-2 1,2,4,5-tetramethylbenzene 

Downstream Products

• 70389-19-4 2,6,10,14-tetrathia-8(1,4,2,5)-benzena-4,12(2,6)-dipyridina-spiro[7.7]pentadecaphane 
• 117912-00-2 2-(2,4,5-Tris-carbamimidoylsulfanylmethyl-benzyl)-isothiourea; hydrobromide 
• 139079-66-6 [{9-[Bis-(diethoxy-phosphoryl)-methylene]-7,11-dihydro-1H,5H-2,4,8,10-tetrathia-benzo[1,2;4,5]dicyclohepten-3-ylidene}-(diethoxy-phosphoryl)-methyl]-phosphonic acid diethyl ester 
• 128844-26-8 N,N'-bis(4-tert-butylphenyl)-1,2,3,4,5,6,7,8-octahydro-2,3,6,7-anthracenetetracarboxylic 2,3:6,7-diimide 
• 117408-73-8 Benzo<1,2-g;4,5-g'>bis<1,3>dithiolo<4,5-b><1,4>dithiocine-2,10-dithione 
• 132425-06-0 benzene-1,2,4,5-tetra(methylenephosphonate de diiospropyle) 
• 140652-74-0 1,2,3,4,5,6,7,8-Octahydro-2,2,3,3,6,6,7,7-octa(ethoxycarbonyl)-anthracen 
• 145984-11-8 5,6-Bis(brommethyl)-1,3-dihydroinden-2,2-diyl-2,2-diphosphonsaeuretetraethylester 
• 145984-10-7 1,3,5,7-Tetrahydro-s-indacen-2,6-bis(diyl-diphosphonsaeuretetraethylester) 
• 82457-00-9 C₂₀H₂₀S₄ 
• 82457-01-0 C₂₀H₂₀S₄ 
• 87837-08-9 2-[2,4,5-tris(cyanomethyl)phenyl]acetonitrile 
• 810-97-9 1,2,4,5-tetrakis-(phenylthiomethyl)benzene 
• 128844-27-9 N,N'-bis(2,5-di-tert-butylphenyl)-1,2,3,4,5,6,7,8-octahydro-2,3,6,7-anthracenetetracarboxylic 2,3:6,7-diimide 

Related news

Diversity-oriented approach to novel spirocycles via 1,2,4,5-tetrakis(bromomethyl)benzene under operationally simple reaction conditions08/16/2019

Here, we have established a simple and an efficient methodology for the synthesis of spirocyclic α-amino acids as well as spirosulfones starting with readily available active methylene compounds (AMCs). The key di-bromo building blocks were assembled by reacting various active methylene compoun...detailed

Relevant academic research and scientific papers

N-Spirocyclic Quaternary Ammonium Ionenes for Anion-Exchange Membranes

The development of cationic polymers for anion-exchange membranes (AEMs) with high alkaline stability and conductivity is a considerable challenge in materials chemistry. In response, we here present the synthesis and properties of N-spirocyclic quaternary ammonium ionenes (spiro-ionenes) containing 5- and 6-membered rings fused by central nitrogen cations. High-molecular weight and film-forming spiro-ionenes are successfully synthesized in cyclo-polycondensations of tetrakis(bromomethyl)benzene and dipiperidines under mild conditions. These polyelectrolytes show excellent thermal and alkaline stability with no degradation detected by NMR spectroscopy after more than 1800 h in 1 M KOD/D2O at 80 °C. Even at 120 °C, the spiro-ionenes display reasonable alkaline stability. Transparent and mechanically robust AEMs based on ionically cross-linked blends of spiro-ionene and polybenzimidazole reach OH- conductivities up to 0.12 S cm-1 at 90 °C. The current findings demonstrate that spiro-ionenes constitute a new class of alkali-stable anion-exchange polymers and membranes.

Diversity-oriented approach to spirooxindoles: Application of a green reagent 'rongalite'

Abstract A range of functionalized spirooxindole derivatives have been assembled via the Diels-Alder (DA) reaction. Here, rongalite has been used to generate the key sultine building blocks which are useful latent diene equivalents in the DA chemistry. The di-bromo intermediates used here are produced by reacting the 1,2,4,5-tetrakis(bromomethyl)benzene with protected oxindole derivatives under operationally simple reaction conditions. In our study, we avoided the isolation of various intermediates, and thus reduced the cost and efforts related to the overall process.

1,2,4,5-Tetrakis(trimethylsilylmethyl)-benzene at 150 K

The title compound, C22H46Si4, crystallizes in space group Fddd with crystallographic symmetry 222. Steric overcrowding by the bulky ligands is avoided by arranging the trimethylsilyl groups alternately above and below the benzene plane in skeletal D2 symmetry.

Synthesis and electrical properties of crosslinked poly(1,2,4,5-phenylenedivinylene) and copolymers

Crosslinked conjugated conducting polymer, poly(1,2,4,5-penylene divinylene)(PPDV) and its copolymers were prepared by the water-soluble precursor method. The spectral characteristics of these materials have been investigated by using UV-visible and FT-IR spectroscopy. PPDV hemopolymer film could not be stretched due to its crosslinked structure, so this homopolymer could slightly be duped with strong oxidant, FeCl3, to produce a very low conductivity value of 3×10-6 Scm-1. However, copolymers containing PDV units and DMPV units showed considerably high conductivities ranging from 3×10-2 to 68 Scm-1, when doped with FeCl3, depending upon the copolymer composition.

Secondary interactions in bromomethyl-substituted benzenes: Crystal structures of three α,α′-bis-bromoxylenes, 1,2,3,5-tetrakis(bromomethyl)benzene, and 1,2,4,5-tetrakis(bromomethyl)benzene

X-Ray structure determinations of all three isomers of bis(bromomethyl) benzene and of two isomeric tetrakis(bromomethyl)benzenes show that the packing of the molecules is determined principally by interactions of the bromomethyl groups (C-H ? Br and Br ? Br), except for ortho-bis (bromomethyl)benzene, in which C-H ? π interactions play a major role.

Catalyst-Controlled Transannular Polyketide Cyclization Cascades: Selective Folding of Macrocyclic Polyketides

The biomimetic synthesis of aromatic polyketides from macrocyclic substrates by means of catalyst-controlled transannular cyclization cascades is described. The macrocyclic substrates, which feature increased stability and fewer conformational states, were thereby transformed into several distinct polyketide scaffolds. The catalyst-controlled transannular cyclizations selectively led to aromatic polyketides with a defined folding and oxygenation pattern, thus emulating β-keto-processing steps of polyketide biosynthesis.

Tuning Intrinsic and Extrinsic Proton Conduction in Metal-Organic Frameworks by the Lanthanide Contraction

Seven isomorphous lanthanide metal-organic frameworks in the PCMOF-5 family, [Ln(H5L)(H2O)n](H2O) (L = 1,2,4,5-tetrakis(phosphonomethyl)benzene, Ln = La, Ce, Pr, Nd, Sm, Eu, Gd) have been synthesized and characterized. This family contains 1-D water-filled channels lined with free hydrogen phosphonate groups and gives a very low activation energy pathway for proton transfer. The lanthanide contraction was employed to systematically vary the unit cell dimensions and tune the proton conducting pathways. LeBail fitting of the crystalline series shows that the crystallographic a-axis, along the channel, can be varied in increments less than 0.02 ? correspondingly shortening the proton transfer pathway. The proton conductivities for the La and Pr complexes were roughly an order of magnitude higher than other members of the series (10-3 S cm-1 versus 10-4 S cm-1). Single crystal structures of the high and low conducting members of the series (La, Pr for high and Ce for low) affirm the structural similarities extend beyond the unit cell parameters to positions of free acid groups and included water molecules. Scanning electron microscopy reveals marked differences in particle size of the different members of the Ln series owing to lattice strain effects induced by changing the lanthanide. Notably, the high conducting La and Pr complexes have the largest particle sizes. This result contradicts any notion that degradation of the MOF at grain boundaries is enabling the observed conductivity as proton conduction dominated by extrinsic pathways would be enabled by small particles (i.e., the La and Pr complexes would be the worst conductors). Proton conductivity measurements of a ball milled sample of the La complex corroborate this result.

Synthesis, structure, surface and antimicrobial properties of new oligomeric quaternary ammonium salts with aromatic spacers

New dimeric, trimeric and tetrameric quaternary ammonium salts were accomplished by reaction of tertiary alkyldimethyl amines with appropriate bromomethylbenzene derivatives. A series of new cationic surfactants contain different alkyl chain lengths (C4-C18), aromatic spacers and different numbers of quaternary nitrogen atoms. The structure of the products was confirmed by spectral analysis (FT-IR, 1H-NMR, 13C-NMR and 2D-NMR), mass spectroscopy (ESI-MS), elemental analysis, as well as PM5 semiempirical methods. Compound (21) was also analyzed using X-ray crystallography. Critical micelle concentration (CMC) of 1,4-bis-[N-(1-alkyl)-N,N-dimethylammoniummethyl]benzene dibromides (3-9) was determined to characterize the aggregation behavior. The antimicrobial properties of novel QACs (Quaternary Ammonium Salts) were examined to set their minimal inhibitory concentration (MIC) values against fungi Aspergillus Niger, Candida albicans, Penicillium chrysogenum and bacteria Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa.

A cascade Aza-Cope/Aza-prins cyclization leading to piperidine derivatives

The cascade aza-Cope/aza-Prins cyclization of homoallylamines to give substituted piperidines has been explored. The use of glyoxalic acid as the carbonyl component afforded bicyclic structures as a result of the internal carboxylate anion trapping the intermediate cation. The unimolecular bis-, tris-, and tetrakis(homoallylamine)s efficiently delivered the appended bis-, tris- and tetrakis(piperidine-4-ol)s (tripod and crucifix shape, respectively) as new entities. The latter compound served as an excellent ligand in the Suzuki-Miyaura cross-coupling reaction to synthesize incrustoporin. The cascade aza-Cope/aza-Prins cyclization of homoallylamines to give substituted piperidines is described. A unimolecular tetrapiperidine derivative, which resulted from this strategy, was employed as a ligand in the Suzuki-Miyaura cross-coupling reaction of an α-iodobutenolide with an arylboronic acid in an efficient synthesis of incrustoporin and its analogues.

Diversity oriented approach to oxepine derivatives: further expansion via diels?Alder reaction

Oxepine derivatives have been assembled via Diels?Alder (DA) reaction as a key step and the latent dienes suitable for the DA reaction have been generated in situ from the sultine derivatives, which in turn were achieved by using commercially available rongalite. The "drug like" molecules assembled here may find useful applications in medicinal as well as bioorganic chemistry.