2675-79-8

Usage

Uses

Used in Organic Synthesis:
1-Bromo-3,4,5-trimethoxybenzene is used as a key intermediate in organic synthesis for the production of various chemical compounds. Its unique structure allows for a wide range of reactions, making it a valuable building block in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-Bromo-3,4,5-trimethoxybenzene is used as a starting material for the synthesis of various drugs and drug candidates. Its ability to be easily modified and functionalized makes it a promising candidate for the development of new therapeutic agents.
Used in Agrochemicals:
1-Bromo-3,4,5-trimethoxybenzene is also utilized in the agrochemical industry as a precursor for the synthesis of various pesticides and agrochemical products. Its versatility in chemical reactions allows for the creation of effective and targeted pest control solutions.
Used in Dye Industry:
In the dye industry, 1-Bromo-3,4,5-trimethoxybenzene is used as a raw material for the production of dyes and pigments. Its chemical properties enable the development of a wide range of colorants with different shades and properties, catering to various applications and industries.
Overall, 1-Bromo-3,4,5-trimethoxybenzene is a versatile and valuable compound with applications in various industries, including organic synthesis, pharmaceuticals, agrochemicals, and dyestuff. Its unique structure and chemical properties make it an essential component in the development of new and innovative products.

InChI:InChI=1/C9H11BrO3/c1-11-7-4-6(10)5-8(12-2)9(7)13-3/h4-5H,1-3H3

Upstream product

• 70654-71-6 4-bromo-2,6-dimethoxyphenol 
• 77-78-1 dimethyl sulfate 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 24313-88-0 3,4,5-Trimethoxyaniline 
• 118-41-2 Eudesmic acid 
• 38790-07-7 5-bromo-3-methoxybenzene-1,2-diol 
• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 2539-27-7 3,4,5-tribromo-2,6-dimethoxyphenol 
• 5034-74-2 5-bromo-3-methoxysalicylaldehyde 
• 16492-75-4 5-bromo-1,2,3 trihydroxybenzene 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 213596-33-9 2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane 
• 634-36-6 1,2,3-trimethoxybenzene 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 79117-98-9 methyl 4-(3,4,5-trimethoxyphenyl)butanoate 
• 137744-79-7 methyl (E)-4-(3,4,5-trimethoxyphenyl)but-3-enoate 
• 112221-37-1 5-(2,6-Dimethoxy-phenoxy)-1,2,3-trimethoxy-benzene 
• 76284-02-1 2-benzyl-6-exo-hydroxy-6-endo-3',4',5'-trimethoxyphenyl-2-azabicyclo<2.2.2>octane 
• 127404-78-8 4-(3,4,5-trimethoxy-phenyl)-but-3-enoic acid 
• 112221-39-3 C₁₈H₂₂O₇ 
• 110087-29-1 3-(6-Bromo-benzo[1,3]dioxol-5-yl)-2-cyano-3-(3,4,5-trimethoxy-phenyl)-propionic acid methyl ester 
• 99124-63-7 cis-tetrahydro-2,5-bis(3,4,5-trimethoxyphenyl)furan 
• 99103-35-2 trans-tetrahydro-2,5-bis(3,4,5-trimethoxyphenyl)furan 
• 138745-81-0 tetrahydro-2-methoxy-5-(3,4,5-trimethoxyphenyl)furan 
• 140705-14-2 (2S,5S)-2-(3',4',5'-trimethoxyphenyl)-5-[3-methoxy-5-(2'-t-butyldimethylsilyloxyethanesulfonyl)-4-propoxyphenyl]tetrahydrofuran 
• 94670-93-6 α-(3,4,5-trimethoxyphenyl)-6-bromobenzo-1,3-dioxole-5-methanol 
• 81952-70-7 1-(3,4,5-Trimethoxy-phenyl)-cyclohexanol 
• 112221-36-0 1,2,3-Trimethoxy-5-(4-methoxy-phenoxy)-benzene 

Relevant academic research and scientific papers

Synthetic method 5 - bromo -1 and 2,3 - trimethoxy benzene

The synthesis method of 5 -bromo -1-2,3 -methoxy benzene comprises the following steps: S1, taking the vanillin as a starting raw material, and brominating 5 - bromo -2 - hydroxyl -3 -methoxybenzaldehyde through the hydroxyl group para-position. S2 is obt

Orthogonal Stability and Reactivity of Aryl Germanes Enables Rapid and Selective (Multi)Halogenations

While halogenation is of key importance in synthesis and radioimaging, the currently available repertoire is largely designed to introduce a single halogen per molecule. This report makes the selective introduction of several different halogens accessible. Showcased here is the privileged stability of nontoxic aryl germanes under harsh fluorination conditions (that allow selective fluorination in their presence), while displaying superior reactivity and functional-group tolerance in electrophilic iodinations and brominations, outcompeting silanes or boronic esters under rapid and additive-free conditions. Mechanistic experiments and computational studies suggest a concerted electrophilic aromatic substitution as the underlying mechanism.

New procedure for the highly regioselective aerobic bromination of aromatic compounds using copper-based nanocatalyst

A new procedure for the highly regioselective aerobic bromination of aromatic compounds in the presence of copper-based nanoparticles (CuO/ZnO nanocatalyst) under reflux condition is described. Mechanistic parameters are discussed and the plausible mechanism is proposed. Recyclability of the CuO/ZnO nanocatalyst has also been explored upon aerobic bromination of aromatic compounds.

PROCESS FOR PRODUCTION OF OXIDATION REACTION PRODUCT OF AROMATIC COMPOUND

The present invention provides a process for producing an oxidation reaction product of an aromatic compound, having excellent environmental load reduction performance, cost reduction performance, etc. Provided is a process for producing an oxidation reaction product of a raw material aromatic compound by reacting the raw material aromatic compound with an oxidizing agent. The process further uses an electron donor-acceptor linked molecule. The process includes the step of: reacting the electron donor-acceptor linked molecule in an electron-transfer state, the oxidizing agent, and the raw material aromatic compound, thereby generating an oxidation reaction product resulting from oxidation of the raw material aromatic compound.

Predicting the structure of supramolecular dendrimers via the analysis of libraries of AB3 and constitutional isomeric AB2 biphenylpropyl ether self-assembling dendrons

The synthesis of 4′-hydroxy-4-biphenylpropionic, 3′,4′- dihydroxy-4-biphenylpropionic, 3′,5′-dihydroxy-4-biphenylpropionic, and 3′,4′,5′-trihydroxy-4-biphenylpropionic methyl esters via three efficient and modular strategies including one based on Ni-catalyzed borylation and sequential cross-coupling is reported. These building blocks were employed in a convergent iterative approach to the synthesis of one library of 3,4,5-trisubstituted and two libraries of constitutional isomeric 3,4- and 3,5-disubstituted biphenylpropyl ether dendrons. Structural and retrostructural analysis of supramolecular dendrimers revealed that biphenylpropyl ether dendrons self-assemble and self-organize into the same periodic lattices and quasi-periodic arrays observed in previously reported libraries, but with larger dimensions, different mechanisms of self-assembly, and improved solubility, thermal, acidic, and oxidative stability. The different mechanisms of self-assembly led to the discovery of two new supramolecular structures. The first represents a new banana-like lamellar crystal with a four layer repeat. The second is a giant vesicular sphere self-assembled from 770 dendrons that exhibits an ultrahigh molar mass of 1.73 × 106 g/mol. Thus, the enhanced size of the self-assembled structures constructed from biphenylpropyl ether dendrons permitted for the first time discrimination of various molecular mechanisms of spherical self-assembly and elaborated a continuum between small filled spheres and very large hollow spheres that is dictated by the primary structure of the dendron. The comparative analysis of libraries of biphenylpropyl ether dendrons with the previously reported libraries of benzyl-, phenylpropyl-, and biphenyl-4-methyl ether dendrons demonstrated biomimetic self-assembly wherein the primary structure of the dendron and to a lesser extent the structure of its repeat unit determines the supramolecular tertiary structure. A "nanoperiodic table" of self-assembling dendrons and supramolecular dendrimers that allows the prediction of the general features of tertiary structures from primary structures was elaborated.

PROCESSES FOR THE PREPARATION OF BIPHENYL COMPOUNDS

The invention concerns processes for the synthesis of a compound of the formula: wherein: R1 and R2 are each, independently, C1-C12 alkyl, CO2R3, OR4, R5(OR6), or C6-C18 aiyl; R3 -R6 are each, independently, C1-C12 alkyl or C6-C12 aryl; and n and m are each, independently, O or an integer from 1-5; said process comprising: — contacting a compound of the formula H0-R7-0H with BH3 and a compound of the formula in the presence of a nickel-containing catalyst to produce a first product, where R7 is a C2-C12 hydrocarbon group and X is a halogen, OMs or OTs; — contacting the first product in situ with a compound of the formula: in the presence of a nickel-containing catalyst to produce a compound of formula I, where Z is a halogen.

Investigation of the mechanism of action of pyrogallol-phloroglucinol transhydroxylase by using putative intermediates

Pyrogallol-phloroglucinol transhydroxylase from Pelobacter acidigallici, a molybdopterin-containing enzyme, catalyzes a key reaction in the anaerobic degradation of aromatic compounds. In vitro, the enzymatic reaction requires 1,2,3,5-tetrahydroxy-benzene as a cocatalyst and the trans-hydroxylation occurs without exchange with hydroxy groups from water. To test our previous proposal that the transfer of the hydroxy group occurs via 2,4,6,3′,4′, 5′-hexahydroxydiphenyl ether as an intermediate, we synthesized this compound and investigated its properties. We also describe the synthesis and characterization of 3,4,5,3′,4′,5′-hexahydroxydiphenyl ether. Both compounds could substitute for the cocatalyst in vitro. This indicates that the diphenyl ethers can intrude into the active site and initiate the catalytic cycle. Recently, the X-ray crystal structure of the transhydroxylase (TH) was published[16] and it supports the proposed mechanism of hydroxy-group transfer.

Exploring and expanding the structural diversity of self-assembling dendrons through combinations of AB, constitutional isomeric AB2, and AB3 biphenyl-4-methyl ether building blocks

General, efficient and inexpensive methods for the synthesis of dendritic building blocks methyl 3′,4′-dihydroxybiphenyl-4-carboxylate, 3′,5′-dihydroxybiphenyl-4-carboxylate, and methyl 3′,4′,5′-trihydroxybiphenyl-4-carboxylate were elaborated. In all syntheses the major step involved an inexpensive NiII-catalyzed Suzuki cross-coupling reaction. These three building blocks were employed together with methyl 4′-hydroxybiphenyl-4-carboxylate in a convergent iterative strategy to synthesize seven libraries containing up to three generations of 3′,4′-, 3′,5′-, and 3′,4′,5′-substituted biphenyl-4-methyl ether based amphiphilic dendrons. These dendrons self-assemble into supramolecular dendrimers that self-organize into periodic assemblies. Structural and retrostructural analysis of their assemblies demonstrated that these dendrons self-assemble into hollow and non-hollow supramolecular dendrimers exhibiting dimensions of up to twice those reported for architecturally related dendrons based on benzyl ether repeat units. These new dendrons expand the structural diversity and demonstrate the generality of the concept of self-assembling dendrons based on amphiphilic arylmethyl ethers.

Tetraphenylethene-derived columnar liquid crystals and their oxidative photocyclization

The synthesis of novel tetraphenylethenes 9a-f, 13, and 18a,b bearing ether, biphenyl, and 4-cyanobiphenyl moieties via a McMurry reaction and Suzuki coupling as key steps is described. Mesogenic properties of these compounds were studied by differential

Non-steroidal ligands for the glucocorticoid receptor, compositions and uses thereof

The invention provides non-steroidal ligands for the glucocorticoid receptor, methods for making non-steroidal ligands of the glucocorticoid receptor, compositions of non-steroidal ligands of the glucocorticoid receptor and methods of using non-steroidal