174671-92-2

Basic information

• Product Name: 5-METHOXYBENZO[C][1,2]OXABOROL-1(3H)-OL
• Synonyms: 5-METHOXYBENZO[C][1,2]OXABOROL-1(3H)-OL;1,3-dihydro-5-methoxy-1-hydroxy-2,1-benzoxaborole
• CAS NO: 174671-92-2
• Molecular Formula: C₈H₉BO₃
• Molecular Weight: 163.97
• Mol File: 174671-92-2.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-METHOXYBENZO[C][1,2]OXABOROL-1(3H)-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXYBENZO[C][1,2]OXABOROL-1(3H)-OL(174671-92-2)
• EPA Substance Registry System: 5-METHOXYBENZO[C][1,2]OXABOROL-1(3H)-OL(174671-92-2)

Safety Data

• Hazardous Substances Data: 174671-92-2(Hazardous Substances Data)

Upstream product

• 1447933-44-9 2-(2-bromomethyl-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 27060-75-9 4-bromo-3-methylanisole 
• 7507-86-0 2-bromo-5-methoxy-benzaldehyde 
• 1132669-90-9 5-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde 
• 688-74-4 boric acid tributyl ester 
• 150192-39-5 2-Bromo-5-methoxybenzyl alcohol 
• 651326-66-8 1-bromo-2-(1-ethoxyethoxymethyl)-4-methoxybenzene 
• 848483-68-1 2-bromo-5-methoxy-1-(methoxymethoxymethyl)benzene 
• 22921-68-2 2-bromo-5-methoxy-benzoic acid 

Downstream Products

• 1187190-70-0 1,3-dihydro-1,5-dihydroxy-2,1-benzoxaborolane 

Relevant articles and documents

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

Substituent effects on oxidation-induced formation of quinone methides from arylboronic ester precursors

A series of arylboronic esters containing different aromatic substituents and various benzylic leaving groups (Br or N+Me3Br -) have been synthesized. The substituent effects on their reactivity with H2O2 and formation of quinone methide (QM) have been investigated. NMR spectroscopy and ethyl vinyl ether (EVE) trapping experiments were used to determine the reaction mechanism and QM formation, respectively. QMs were not generated during oxidative cleavage of the boronic esters but by subsequent transformation of the phenol products under physiological conditions. The oxidative deboronation is facilitated by electron-withdrawing substituents, such as aromatic F, NO2, or benzylic N+Me 3Br-, whereas electron-donating substituents or a better leaving group favor QM generation. Compounds containing an aromatic CH 3 or OMe group, or a good leaving group (Br), efficiently generate QMs under physiological conditions. Finally, a quantitative relationship between the structure and activity has been established for the arylboronic esters by using a Hammett plot. The reactivity of the arylboronic acids/esters and the inhibition or facilitation of QM formation can now be predictably adjusted. This adjustment is important as some applications may benefit and others may be limited by QM generation. Tunable quinone methide formation: Aromatic substituents and the benzylic leaving group strongly affect the H 2O2-induced formation of quinone methides (QMs) from arylboronic esters (see scheme). The reactivity of arylboronic esters can be predictably adjusted by varying substituents. Copyright

Hydrolytically-Resistant Boron-Containing Therapeutics And Methods Of Use

Compositions and methods of use of boron derivatives, including benzoxaboroles, benzazaboroles and benzthiaboroles, as therapeutic agents for treatment of diseases caused by fungi, yeast, bacteria or viruses are disclosed, as well as methods for synthesis of said agents and compositions thereof.