94111-75-8

Usage

Uses

Used in Pharmaceutical Industry:
3,5-bis(bromomethyl)benzoic acid is used as a key intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
3,5-bis(bromomethyl)benzoic acid serves as a building block in the creation of agrochemicals, playing a role in the development of pesticides and other agricultural chemicals to enhance crop protection and yield.
Used in Material Science:
3,5-bis(bromomethyl)benzoic acid is utilized as a component in the synthesis of advanced materials, contributing to the properties and performance of various material applications.
Used in Dye and Pigment Production:
As a versatile intermediate, 3,5-bis(bromomethyl)benzoic acid is employed in the production of dyes and pigments, enhancing color properties and stability in different industries such as textiles, plastics, and inks.

InChI:InChI=1/C9H8Br2O2/c10-4-6-1-7(5-11)3-8(2-6)9(12)13/h1-3H,4-5H2,(H,12,13)

Upstream product

• 499-06-9 3,5-dimethylbenzoic acid 
• 123065-60-1 3,5-bis(hydroxylmethyl)benzoic acid 
• 145927-73-7 2-(2-{2-[2-(2-methanesulfonyloxyethoxy)ethoxy]ethoxy}ethoxy)tetrahydro-2H-pyran 
• 29333-41-3 methyl 3,5-bis(bromomethyl)benzoate 
• 25081-39-4 methyl 3,5-dimethylbenzoate 
• 6613-44-1 3,5-dimethylbenzoyl chloride 
• 156597-80-7 3,5-Bis(brommethyl)benzoesaeure-tert-butylester 
• 554-95-0 benzene-1,3,5-tricarboxylic acid 
• 2672-58-4 1,3,5-tris-(methoxycarbonyl)benzene 
• 38588-64-6 3,5-bis(methoxycarbonyl)benzoic acid 

Downstream Products

• 94111-76-9 3,5-bis(bromomethyl)benzoic acid chloride 
• 223449-25-0 5-methoxycarbonyl-m-xylylene bisphosphonic acid tetramethyl ester 
• 223449-19-2 5-carboxy-m-xylylenebisphosphonic acid tetramethyl ester 
• 223449-74-9 [3-(4-tert-butoxycarbonylamino-butylcarbamoyl)-5-(dimethoxy-phosphorylmethyl)-benzyl]-phosphonic acid dimethyl ester 

Relevant academic research and scientific papers

NON-PEPTIDIC CELL-PENETRATING MOTIFS

Disclosed are compounds that can penetrate the mitochondrial membrane and that are able to deliver cargo (e.g., therapeutic agents) specifically to the mitochondria.

Synthesis of constrained tetracyclic peptides by consecutive CEPS, CLIPS, and oxime ligation

In Nature, multicyclic peptides constitute a versatile molecule class with various biological functions. For their pharmaceutical exploitation, chemical methodologies that enable selective consecutive macrocyclizations are required. We disclose a combination of enzymatic macrocyclization, CLIPS alkylation, and oxime ligation to prepare tetracyclic peptides. Five new small molecular scaffolds and differently sized model peptides featuring noncanonical amino acids were synthesized. Enzymatic macrocyclization, followed by one-pot scaffold-assisted cyclizations, yielded 21 tetracyclic peptides in a facile and robust manner.

Non-Peptidic Cell-Penetrating Motifs for Mitochondrion-Specific Cargo Delivery

Mitochondrial dysfunction is linked to a variety of human illnesses, but selective delivery of therapeutics into the mitochondrion is challenging. Now a family of amphipathic cell-penetrating motifs (CPMs) is presented, consisting of four guanidinium groups and one or two aromatic hydrophobic groups (naphthalene) assembled through a central scaffold (a benzene ring). The CPMs and CPM-cargo conjugates efficiently enter the interior of cultured mammalian cells and are specifically localized into the mitochondrial matrix, as revealed by high-resolution confocal microscopy. With a membrane-impermeable peptide as cargo, the CPMs exhibited ≥170-fold higher delivery efficiency than previous mitochondrial delivery vehicles. Conjugation of a small-molecule inhibitor of heat shock protein 90 to a CPM resulted in accumulation of the inhibitor inside the mitochondrial matrix with greatly enhanced anticancer activity. The CPMs showed minimal effect on the viability or the mitochondrial membrane potential of mammalian cells.

General and Facile Route to Isomerically Pure Tricyclic Peptides Based on Templated Tandem CLIPS/CuAAC Cyclizations

We report a one-pot ligation/cyclization technology for the rapid and clean conversion of linear peptides into tricyclic peptides that is based on using tetravalent scaffolds containing two benzyl bromide and two alkyne moieties. These react via CLIPS/CuAAC reactions with cysteines and azides in the peptide. Flexibility in the scaffolds is key to the formation of isomerically pure products as the flexible scaffolds T41 and T42 mostly promote the formation of single isomeric tricycles while the rigid scaffolds T43 and T44 do not yield clean products. There seems to be no limitation to the number and types of amino acids present as 18 canonical amino acids were successfully implemented. We also observed that azides at the peptide termini and cysteine residues in the center gave better results than compounds with the functional groups placed the other way round.

MULTICYCLIC PEPTIDES AND METHODS FOR THEIR PREPARATION

The invention relates to methods for preparing a compound comprising a peptide attached to a molecular scaffold whereby multiple peptide loops are formed, to compounds that can be obtained with such methods and uses thereof.

Reduction response containing double-disulfide bond of chemical connector and its preparation and use (by machine translation)

Reduction response containing double-disulfide bond of chemical connector and its preparation and use thereof, relates to a double-mercapto compound and its forming with double-disulfide bond of chemical linker, based on the non-coherent double-two-sulfur of the synergistic effect of the tenon, construction with unique oxidation-reduction response dynamic covalent linkage. The covalent linkage with traditional single disulfide bond completely different oxidation-reduction response; its low reducing agent concentration or extracellular conditions having ultra high stability, such as in the cell in the strong reducing conditions can occur under rapid reduction of the fracture. It is expected to be applied to the drug release and biological sensing field, constructing the oxidation-reduction responsive drug delivery system, such as the monoclonal antibody - such as the drug in the sample. (by machine translation)

Synthesis of 3,5-bis(phosphonomethyl)benzoic acid and its application as a metal oxide surface bivalent anchor

A protected form of 3,5-bis(phosphonomethyl)benzoic acid (Bpb-OH), a metal oxide surface bivalent anchor, has been synthesized, coupled to an amine functionality, deprotected, and shown to bind to metal oxide surfaces. The protected anchor, 3,5-bis(dimethoxyphosphinylmethyl)benzoic acid (Me4Bpb-OH) was synthesized in 23% yield over four steps, coupled to a proline-chromophore, deprotected with a solution of iodotrimethylsilane (TMSI) in acetonitrile and adsorbed to Tin(IV)-doped indium oxide and nanocrystalline TiO2 electrodes at surface coverages of 1.5 x 10-10 mol cm-2 and 4.9 x 10-11 mol cm-2, respectively. Finally, Me4Bpb-OH was converted to an amino derivative by attaching a diamino butane linker.

Regiospecific synthesis of 3,5-bis(bromomethyl)benzoic acid, a cysteine crosslinking agent

Bridging two molecules of an organic thiol with the 3,5-dimethylenebenzoic acid (Dmb) group produces a rigid five-carbon Dmb crosslink that is stable to disulfide reducing agents. Radical bromination of 3,5-dimethylbenzoic acid or its succinimido ester gave four α-brominated products. So NMR-pure 3,5-bis(bromomethyl)benzoic acid (Br2Dmb) was regiospecifically synthesized in 38% overall yield by a four-step route from 1,3,5-benzenetricarboxylic acid. S-Alkylation of cysteine methyl ester, a model thiol, with Br2Dmb provided the 2:1 adduct (Cys-OCH3)2Dmb in 79% yield. Subsequent N-protection with di(tert-butyl) dicarbonate gave (Boc-Cys-OCH3)2Dmb in 60% overall yield from cysteine methyl ester. This protected diamino acid is suitable for assembly of two Dmb-crosslinked peptide chains.

Amplifier molecules for enhancement of diagnosis and therapy

Disclosed are amplifier molecules: various organic compounds having branched structures terminating with amine groups to which pharmacologically active groups can be chemically attached. A number of MRI contrast-enhancing agents were synthesized, each comprising plural active groups, such as stable nitroxides and complexes of trivalent metal cations. Such syntheses were successfully performed using a number of amplifiers having different branched structures, demonstrating the general utility of the pertinent chemistry in the synthesis of amplifiers having any of a wide variety of pharmacologically active groups. Amplifiers were also synthesized having linkers terminating with chemically reactive groups such as isothiocyanates, which render the amplifier bifunctional: attachable to polymers, biomacromolecules, or other biocompatible entity possessing multiple reactive sites such as terminal amines. Via such chemistry, the amplifiers are attachable to monoclonal antibodies for concentration of pharmacologically active groups at a desired site in the body.

Synthesis and Characterization of Blocked and Ligand-Appended Hemes Derived from Atropisomeric meso-Diphenylporphyrins

The synthesis of a series of sterically blocked and imidazole-appended meso-diphenyletioporphyrins is described.These hybrid porphyrins have good solubility and spectroscopic properties of β-substituted porphyrins as well as the orientation specificity of ortho-position-derivatized tetraphenylporphyrins.The effectiveness of the blocking groups is demonstrated by ferric hemin hydroxide formation in the doubly protected trans-5,15-bis-2,8,12,18-tetraethyl-3,7,13,17-tetramethylporphine, characterized by UV-visible, 1H NMR, and IR spectra and cyclic voltammetry.The advantage of the m-benzyl linkage in enforcing imidazole coordination to ferric hemes is demonstrated by 1H NMR studies on various type of imidazole-appended heme complexes.Several potential binucleating systems have also been prepared by incorporating nonheme chelating ligands to the hybrid porphyrins.