91-13-4

Usage

Uses

1,2-Bis(bromomethyl)benzene is used in the synthesis of isothioureas, which are compounds that inhibit human nitric oxide synthases. Nitric oxide synthases are enzymes that catalyze the production of nitric oxide, a molecule involved in various physiological processes, including vasodilation, neurotransmission, and immune response. Inhibition of these enzymes can be beneficial in treating conditions associated with excessive nitric oxide production, such as certain inflammatory and neurological disorders.
Used in Pharmaceutical Industry:
1,2-Bis(bromomethyl)benzene is used as a key intermediate in the synthesis of tridentate carbene ligands. Tridentate carbene ligands are a class of compounds that can form three coordinate bonds with a metal center, providing a stable and versatile platform for various applications. In the pharmaceutical industry, these ligands are used in the development of metal-based drugs, which have potential applications in the treatment of cancer, bacterial infections, and other diseases.
Additionally, 1,2-bis(bromomethyl)benzene can be used as a building block in the synthesis of various organic compounds, such as polymers, dyes, and other specialty chemicals. Its reactivity and structural features make it a valuable component in the development of new materials and products across different industries.

Purification Methods

Crystallise it from CHCl3 or pet ether, and/or distil it under vacuum. [Wenner Org Chem 17 527 1952, Beilstein 5 H 366, 5 I 180, 5 II 285, 5 III 819, 5 IV 929.]

Upstream product

• 95-47-6 o-xylene 
• 34904-98-8 2-phenoxymethyl-benzyl alcohol 
• 89-92-9 2-methylbenzyl bromide 
• 79985-01-6 α,α-dibromo-o-xylene 
• 612-14-6 phthalyl alcohol 
• 89-95-2 2-methyl-benzyl alcohol 
• 168971-56-0 2-phenoxymethyl-benzylamine 
• 85-44-9 phthalic anhydride 

Downstream Products

• 42595-43-7 1,1'-bis(pyridinium)-1,2-phenyldimethylene dibromide 
• 110491-34-4 3,3'-dihydroxy-1,1'-o-xylylene-bis-pyridinium; dibromide 
• 7463-07-2 2,3,4,5,6,7-hexahydro-spiro[azepine-1,2'-isoindolinium]; bromide 
• 117135-94-1 2-cyclohexyl-isoindoline 
• 16464-64-5 benzene-1,2-bismethaneisothiouronium dibromide 
• 19375-67-8 2-phenylisoindoline 
• 70276-72-1 N,N'-(1,2-phenylenebis(methylene))dianiline 
• 122679-47-4 phthalan-1,3-dione-bis-(4-dimethylamino-phenylimine) 
• 17300-02-6 1,2-benzenedimethanamine 
• 113439-96-6 2-(2,6-dimethylphenyl)isoindoline 
• 103268-64-0 N,N'-bis-(2,6-dimethyl-phenyl)-o-xylylenediamine 
• 18412-14-1 hexa-Si-methyl-Si,Si'-o-xylylene-bis-silane 
• 5707-27-7 1,2-bis(methoxymethyl)benzene 
• 195526-18-2 1,2-bis-(benzylsulfanyl-methyl)-benzene 

Relevant academic research and scientific papers

Completely regioselective, highly stereoselective syntheses of cis-Bisfullerene[60] adducts of 6,13-disubstituted pentacenes

(Matrix Presented) cis-Bisfullerene[60] adducts of 6,13-disubstituted pentacenes (R = Ph, 4′-hydroxymethylphenyl) are synthesized in 75percent to 85percent isolated yields under kinetically controlled Diels-Alder conditions. The cycloadditions are completely regioselective and highly stereoselective, with only traces of the diastereomeric trans-bisfullerene[60] adducts forming.

Synthesis and electrochemical characterization of a new benzodioxocine-fused poly(: N -methylpyrrole) derivative: A joint experimental and DFT study

In this study, our findings from experimental studies were presented on the synthesis of a new electropolymerizable monomer, 2-methyl-5,10-dihydro-2H-benzo[6,7][1,4]dioxocino[2,3-c]pyrrole (XyPMe), regarding the cyclization reaction of diethyl N-methyl-3,4-dihydroxypyrrole-2,5-dicarboxylate and 1,2-bis(bromomethyl)benzene with concomitant hydrolysis and decarboxylation reactions. The critical step in this synthetic pathway was to determine the optimal temperature of decarboxylation utilizing TGA analysis, which decreases in situ polymerization side-product formation significantly. Following the preparation of the target monomer, the electropolymerization reaction was then conducted, and the optoelectronic properties were investigated in detail. In order to better illuminate the effects of N-alkylation and the heterocyclic ring system on the polymer backbones, we have included and theoretically studied the electronic properties of two monomers already synthesized in our laboratory, possessing the butyl group on the pyrrole ring (XyPBu) and the thiophene scaffold on its structure (XyT), and their corresponding oligomers (n = 2 to 11, n indicates the consecutive unit number). This combined experimental and theoretical research provides a pathway for advanced conjugated systems with predictable electronic and structural properties to be established.

Synthesis and computational bandgap engineering of New 3,4-Alkylenedioxypyrrole (ADOP) derivatives and investigation of their electrochromic properties

This research highlights the degree of conformity between our electrochemical and theoretical studies conducted on the newly designed electropolymerizable monomers (BuDOP, BenDOP and BenzoDOP) possessing 3,4-alkylenedioxypyrrole (ADOP) backbone (BuDOP). We tried to select logical enhancing of the structures in a stepwise in order to discuss the effects of benzene (BenDOP) and benzodioxane (BenzoDOP) like aromatic subunits to the electrochromic properties of the target monomers. Following to the completion of the synthetic steps, appropriate structural analyses of monomers were performed (FT-IR, GC-MS, 1H-NMR, 13CNMR). Subsequently, their corresponding polymers were prepared by electrochemical oxidation and characterized. Afterwards, our consecutive efforts have been contributed to theoretical studies in order to obtain information about their structural properties. To this aim, geometry optimizations were carried out using hybrid density functional theory (DFT/B3LYP/LANL2DZ) and HOMO, LUMO energy levels, HOMO-LUMO energy gaps (AE), electron affinity (EA) as well as ionization potential (IP) values were calculated. Theoretical data were then used for identifying the structure-electronic properties relationship and we aimed to determine the electrochromic properties of the studied monomers. Our results from the B3LYP/LANL2DZ calculations indicated that P(BenDOP) has the lowest HOMO-LUMO gap and we predicted that theoretical data were in good agreement with the experimental studies.

Structure-Activity Relationships of Benzamides and Isoindolines Designed as SARS-CoV Protease Inhibitors Effective against SARS-CoV-2

Inhibition of coronavirus (CoV)-encoded papain-like cysteine proteases (PLpro) represents an attractive strategy to treat infections by these important human pathogens. Herein we report on structure-activity relationships (SAR) of the noncovalent active-site directed inhibitor (R)-5-amino-2-methyl-N-(1-(naphthalen-1-yl)ethyl) benzamide (2 b), which is known to bind into the S3 and S4 pockets of the SARS-CoV PLpro. Moreover, we report the discovery of isoindolines as a new class of potent PLpro inhibitors. The studies also provide a deeper understanding of the binding modes of this inhibitor class. Importantly, the inhibitors were also confirmed to inhibit SARS-CoV-2 replication in cell culture suggesting that, due to the high structural similarities of the target proteases, inhibitors identified against SARS-CoV PLpro are valuable starting points for the development of new pan-coronaviral inhibitors.

THIENODIAZEPINE DERIVATIVES AND APPLICATION THEREOF

The present invention relates to a class of thienodiazepine derivatives and an application thereof in the preparation of a drug for the treatment of diseases associated with bromodomain and extra-terminal (BET) Bromodomain inhibitors. Specifically, the present invention relates to compounds represented by formulas (I) and (II), as well as pharmaceutically acceptable salts thereof.

Novel bridged tetradentate fourth subgroup metal complex as well as preparation method and application thereof (by machine translation)

The invention provides a novel bridged tetradentate fourth subgroup metal complex and a preparation method and application thereof, wherein the complex has a formula a structure, the temperature tolerance is good, and the complex can maintain very high catalytic activity under 120 °C, can obtain ultrahigh molecular weight polyethylene, and can catalyze ethylene and norbornene, 1 - hexene and 1 - octene copolymerization reaction to obtain a polymer product with high comonomer insertion rate. (by machine translation)

Formal [5+1] annulation reactions of dielectrophilic peroxides: Facile access to functionalized dihydropyrans

A general [5+1] annulation reaction, which utilized 4-bromo- or 4-mesyloxy-but-2-enyl peroxides as unique five-atom bielectrophilic synthons to participate in the C-C and the subsequent umpolung C-O bond-forming reactions with C1 nucleophiles, has been developed for the facile synthesis of 2,2-disubstituted dihydropyrans in high yields under mild basic conditions. The dihydropyrans, which are readily prepared on a gram scale by this new method, can be flexibly transformed into the biologically important tetrahydropyrans and pyranones in 1-2 steps.

2,3-Dihalo- and 2,3,6,7-Tetrahaloanthracenes by Vollhardt Trimerization

We efficiently synthesized otherwise difficult to obtain 2,3- and 2,3,6,7-halogenated anthracenes with diverse east/west substituents. Key steps involve the (i) Vollhardt cyclization of bis(propargyl)benzenes with bis(trimethylsilyl)acetylene, (ii) halo-desilylation introducing chlorine, bromine, or iodine substituents, and (iii) dehydrogenation. Pd catalysis allows selective functionalization at the anthracenes' east/west positions. A tetrahydropentacene is synthesized and derivatized via the same strategy, employing tetrapropargylbenzene.

Reducing Diastereomorphous Bis(phosphane oxide) Atropisomers to One Atropisomerically Pure Diphosphane: A New Ligand and a Novel Ligand-Preparation Design

1,1′-Biphenyl-2,2′-diphosphanes with an achiral bridge spanning C-5 and C-5′ form atropisomers that are enantiomers. Accessing them in an atropisomerically pure form requires resolving a racemic mixture thereof or of a bis(phosphane oxide) precursor. 1,1′-Biphenyl-2,2′-diphosphanes with a homochiral bridge spanning C-5 and C-5′ form atropisomers that are diastereomers. We synthesized the first compound of this kind 1) atropselectively and 2) under thermodynamic control—seemingly a first-time exploit in diphosphane synthesis. The selectivity-inducing step was a high-temperature reduction of two non-interconverting bis(phosphane oxide) atropisomers (60:40 mixture). It furnished the desired diphosphane atropisomerically pure (and atropconvergently because the yield was 67 %). This diphosphane proved worthwhile in Tsuji–Trost allylations, the Hayashi addition of phenylboronic acid to cyclohexenone, and the asymmetric hydrogenation of methyl acetoacetate (up to 95 % yield and 95 % ee).

Synthesis and Crystal Structure of a Novel Glycoluril Molecular Scaffold

Abstract: A novel glycoluril scaffold 1, namely 1,6-(1,2-xylylene)-3,4-(1,3-dimetheneyl-hexahydropyrimidine)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, was synthesized by the Mannich reaction of 1,6-(1,2-xylylene)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione 5 with propanediamine and paraformaldehyde. The yielded product 1 was confirmed with IR, NMR, EI-MS. X-ray crystallographic technique was also conducted and the result showed the crystal belongs to monoclinic system, space group P21/c with unit cell parameters a?=?10.6892(11)??, b?=?12.1226(9)??, c?=?13.7822(13)??, α?=?90°, β?=?112.620(4)°,γ?=?90°, V?=?1648.5(3)??3, Z?=?4, Dc?=?1.428, Mr?=?354.41, μ?=?0.098?mm?1, F(000)?=?752, R1?=?0.0522 and wR2?=?0.1138. Graphical Abstract: A novel molecular scaffold, containing a heterocyclic ring instead of an aromatic ring, was synthesized by the Mannich reaction based on glycoluril.[Figure not available: see fulltext.]