5735-41-1

Usage

Uses

Used in Pharmaceutical Industry:
1-Hydroxy-2,1-benzoxaborolane is used as a key intermediate for the synthesis of various pharmaceutical compounds. Its ability to form allylic and benzylic alcohols through Suzuki coupling makes it a valuable building block in the development of new drugs and therapeutic agents.
Used in Chemical Synthesis:
1-Hydroxy-2,1-benzoxaborolane is used as a synthetic building block for the preparation of a wide range of organic compounds. Its solid state and reactivity in Suzuki coupling reactions make it a preferred choice for chemists working on the development of new molecules with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Research and Development:
1-Hydroxy-2,1-benzoxaborolane is used as a research tool in the development of new synthetic methods and strategies. Its unique reactivity and compatibility with various reaction conditions make it an attractive candidate for exploring novel chemical transformations and improving existing synthetic routes.

Synthesis Reference(s)

Journal of the American Chemical Society, 80, p. 835, 1958 DOI: 10.1021/ja01537a021

InChI:InChI=1/C7H9BO3/c9-5-6-3-1-2-4-7(6)8(10)11/h1-4,9-11H,5H2

Upstream product

• 5735-42-2 1,3,1',3'-tetrahydro-1,1'-oxy-bis-benzo[c][1,2]oxaborole 
• 5419-55-6 Triisopropyl borate 
• 18982-54-2 o-bromobenzyl alcohol 
• 121-43-7 Trimethyl borate 
• 100299-22-7 tris(2-chloromethyl phenyl)boroxine 
• 1310-73-2 sodium hydroxide 
• 87199-14-2 2-(hydroxymethyl)phenylboronic acid 
• 40138-16-7 2-formylbenzene boronic acid 
• 118-44-5 1-N-ethylnaphthylamine 
• 103-69-5 N-ethyl-N-phenylamine 
• 100-61-8 N-methylaniline 
• 110-91-8 morpholine 
• 892848-97-4 1,3-dihydro-1-hydroxy-3-(4-morpholinyl)-2,1-benzoxaborole 
• 377780-72-8 2-(2-(bromomethyl)phenyl)-4,4,5,5,-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 92987-34-3 1-ethyl-1,3-dihydro-benzo[c][1,2]oxaborole 
• 96983-87-8 1-o-tolyl-1,3-dihydro-benzo[c][1,2]oxaborole 
• 96983-90-3 [2-(3H-benzo[c][1,2]oxaborol-1-yl)-phenyl]-methanol 
• 92987-33-2 1-ethoxy-1,3-dihydro-benzo[c][1,2]oxaborole 
• 96217-68-4 1-phenyl-1,3-dihydro-benzo[c][1,2]oxaborole 
• 96983-89-0 1-benzyloxy-1,3-dihydro-benzo[c][1,2]oxaborole 
• 95515-59-6 1-cyclohexyloxy-1,3-dihydro-benzo[c][1,2]oxaborole 
• 5735-42-2 1,3,1',3'-tetrahydro-1,1'-oxy-bis-benzo[c][1,2]oxaborole 
• 91589-19-4 B-chloro boron napthalide 
• 118803-40-0 1-hydroxy-6-nitro-3H-2,1-benzoxaborole 
• 709016-07-9 (2'-dibenzylamino-4'-nitro-biphenyl-2-yl)-methanol 
• 101295-00-5 1-(3H-benzo[c][1,2]oxaborol-1-yl)-2-(naphthalen-1-ylcarbamoyloxy-methyl)-benzene 
• 1005327-30-9 (E)-4-(benzo[c]oxaborol-1(3H)-yloxy)-1-phenylbut-2-en-1-one 
• 110409-93-3 (E)-4-(phenylmethylene)-3-isochromanone 

Relevant academic research and scientific papers

Transition-metal-free, one-pot synthesis of benzoxaboroles from: O -bromobenzaldehydes via visible-light-promoted borylation

A novel and simple one-pot stepwise method to synthesize benzoxaboroles was demonstrated. This step-by-step synthetic method includes photocatalytic boronization with phenothiazine as a photocatalyst and sequential water-induced reduction in the presence of bis(pinacolato)diboron. A series of o-bromobenzaldehydes were well-tolerated under the standard conditions. In addition, this method has been successfully applied in the synthesis of the anti-tuberculosis candidate drug GSK 3036656 and anti-fungal drug tavaborole. This journal is

Benzoxaborole-1-alcohol compound and preparation method and application thereof

The invention belongs to the field of bactericides, and particularly relates to a benzoxaborole-1-alcohol compound and a preparation method and application thereof. The benzoxaborole-1-alcohol compound has good bactericidal activity, can effectively control tomato early blight, wheat scab, rice sheath blight disease, strawberry gray mold, apple blotch, cucumber anthracnose and other crop diseases,can produce excellent antibacterial effects at low concentration, and shows good selectivity. The compound is used as a leucyl-tRNA synthetase inhibitor, the evolution difference of aminoacyl-tRNA synthetase of germs and eukaryotes is utilized, and the compound has very high safety to non-target organisms while killing the germs and can be used as a bactericide in agriculture.

Inhibiting protein prenylation with benzoxaboroles to target fungal plant pathogens

Fungal pathogens pose an increasing threat to global food security through devastating effects on staple crops and contamination of food supplies with carcinogenic toxins. Widespread deployment of agricultural fungicides has increased crop yields but is driving increasingly frequent resistance to available agents and creating environmental reservoirs of drug-resistant fungi that can also infect susceptible human populations. To uncover non-cross-resistant modes of antifungal action, we leveraged the unique chemical properties of boron chemistry to synthesize novel 6-thiocarbamate benzoxaboroles with broad spectrum activity against diverse fungal plant pathogens. Through whole genome sequencing of Saccharomyces cerevisiae isolates selected for stable resistance to these compounds, we identified mutations in the protein prenylation-related genes, CDC43 and ERG20. Allele-swapping experiments confirmed that point mutations in CDC43, which encodes an essential catalytic subunit within geranylgeranyl transferase I (GGTase I) complex, were sufficient to confer resistance to the benzoxaboroles. Mutations in ERG20, which encodes an upstream farnesyl pyrophosphate synthase in the geranylgeranylation pathway, also conferred resistance. Consistent with impairment of protein prenylation, the compounds disrupted membrane localization of the classical geranylgeranylation substrate Cdc42. Guided by molecular docking predictions, which favored Cdc43 as the most likely direct target, we overexpressed and purified functional GGTase I complex to demonstrate direct binding of benzoxaboroles to it and concentration-dependent inhibition of its transferase activity. Further development of the boron-containing scaffold described here offers a promising path to the development of GGTase I inhibitors as a mechanistically distinct broad spectrum fungicide class with reduced potential for cross-resistance to antifungals in current use.

BORON CONTAINING COMPOUNDS AND THEIR USES

The present disclosure contemplates novel boron-containing compounds and their uses as active agents that exhibit pesticidal activity such as antimicrobial, insecticidal, arachnicidal, and/or anti parasitic activity. An agrochemical composition containing such a compound and its use in, animal health, agriculture, or horticulture is also contemplated. A method for promoting plant performance and/or controlling, reducing, preventing, ameliorating, or inhibiting microbes, insects, arachnids, and/or parasites on or in an animal, a plant, a plant part, plant propagation material, and/or harvested fruits or vegetables is also contemplated.

Synthesis and biological evaluation of arylphosphonium-benzoxaborole conjugates as novel anticancer agents

Arylphosphonium-benzoxaborole conjugates have been synthesized as potential mitochondria targeting anticancer agents. The synthesized compounds have been tested for their effects on cell viability in various solid tumor cell lines including breast cancer 4T1 and MCF-7, pancreatic cancer MIAPaCa-2 and colorectal adenocarcinoma WiDr. Compound 6c is designated as a lead compound for further studies due to its enhanced effects on cell viability in the above-mentioned cell lines. Seahorse Xfe96 based metabolic assays reveal that the lead candidate 6c inhibits mitochondrial respiration in 4T1 and WiDr cell lines as evidenced by the reduction of mitochondrial ATP production and increase in proton leak. Epiflourescent microscopy experiments also illustrate that 6c causes significant mitochondrial fragmentation in 4T1 and WiDr cells, morphologically consistent with programmed cell death. Our current studies illustrate that arylphosphonium-benzoxaborole conjugates have potential to be further developed as anticancer agents.

PROTECTIVE GROUPS AND METHODS FOR PROTECTING BENZOXABOROLES OR OXABOROLES

The present invention relates in part protective groups that can be used to reversibly protect benzoxaboroles and/or oxaboroles and yield the corresponding protected complexes. The invention further relates to the use of these protective groups to protect benzoxaboroles and/or oxaboroles.

Protection of the Benzoxaborole Moiety: Synthesis and Functionalization of Zwitterionic Benzoxaborole Complexes

The synthesis and utility of three benzoxaborole protecting groups are reported. These protecting groups improve organic solubility and allow otherwise incompatible reactions (oxidations, substitutions, and mild reductions) to be achieved in the presence of the benzoxaborole moiety. 3-(N,N-Dimethylamino)-1-propanol was determined to be useful in one-step sequences and is readily cleaved upon workup. Two other groups, N-methylsalicylidenimine and 2-[1-(methylimino)ethyl]phenol, are suitable for multistep syntheses. Deprotection with mild aqueous acid allows for chromatography-free isolation of the benzoxaborole in high yields.

An Efficient Benzoxaborole One-Pot Synthesis by SiliaCat DPP-Pd Heterogeneous Catalysis using Diboronic Acid

Organoboron compounds are valuable molecules of increasing interest in organic synthesis, catalysis, biology and medicine. Among them, benzoxaboroles emerged as promising building blocks for numerous research programs. In this letter, we communicate the development of new conditions for the one-pot benzoxaborole synthesis by SiliaCat DPP?Pd catalysis using diboronic acid as the boron source. This low cost and sustainable strategy permitted the preparation of a useful range of benzoxaborole building blocks. Finally, the transformation was extended to a continuous flow process using our Vapourtec system. (Figure presented.).

A convenient one-pot synthesis of boroxoles from diboronic acid

The preparation of the boroxole motif traditionally relies on a 3-step process and the use of n-butyl lithium that can limit substrate scope. Herein during our exploration toward novel RORγ inhibitors, we identified a convenient one-pot preparation of the motif in good yields with good substrate scope.

FUNCTIONALIZED AMINOBENZOBOROXOLES

Disclosed are functionalized aminobenzoboroxoles compounds, method for preparing these compounds, and methods for treating cancers.