89694-45-1

Usage

Uses

Used in Suzuki Reaction:
5-BROMO-2-METHOXYPHENYLBORONIC ACID is used as a reactant in Suzuki reactions, a type of cross-coupling reaction that facilitates the formation of carbon-carbon bonds between an organoboron compound and an organic halide or triflate. This reaction is widely employed in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and advanced materials.
Used in the Synthesis of Tweezers-like Aromatic Molecules:
5-BROMO-2-METHOXYPHENYLBORONIC ACID is used as a building block in the synthesis of tweezers-like aromatic molecules with luminescent properties. These molecules exhibit unique photophysical properties and have potential applications in the development of fluorescent sensors, molecular probes, and optoelectronic devices.
Used in Suzuki-Miyaura Cross-Coupling Reactions:
5-BROMO-2-METHOXYPHENYLBORONIC ACID is utilized as a reactant in Suzuki-Miyaura cross-coupling reactions, which are a subset of Suzuki reactions that involve the coupling of an organoboron compound with an organic halide or triflate. This reaction is particularly useful for the formation of biaryl and heteroaryl structures, which are common motifs in biologically active compounds and materials with unique electronic properties.

InChI:InChI=1/C7H8BBrO3/c1-12-7-3-2-5(9)4-6(7)8(10)11/h2-4,10-11H,1H3

Upstream product

• 5720-06-9 2-Methoxyphenylboronic acid 
• 688-74-4 boric acid tributyl ester 
• 21702-84-1 2,4-dibromoanisole 

Downstream Products

• 477727-56-3 4-chloro-6-(5-bromo-2-methoxy-phenyl)-pyrimidin-2-yl-amine 
• 852146-22-6 5-(2-methoxy-5-bromophenyl)furan-2-carboxylic acid methyl ester 
• 884010-20-2 2,2-dimethylpropane-1,3-diyl [5-bromo-2-methoxyphenyl] boronate 
• 927384-45-0 4-bromo-2-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-1-methoxybenzene 
• 927384-61-0 C₂₇H₂₅BO₄ 
• 950511-07-6 C₂₈H₂₇BO₅ 
• 927384-56-3 3-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-4,6'-dimethoxy-4''-methyl-1,1':3',1''-terphenyl 
• 927384-64-3 C₃₃H₂₉BO₄ 
• 927384-60-9 4-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-6',6''-dimethoxy-4'''-methyl-1,1':3',1'':3'',1'''-quaterphenyl 
• 927384-58-5 3-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-4,6',6''-trimethoxy-4'''-methyl-1,1':3',1'':3'',1'''-quaterphenyl 
• 927384-62-1 4-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-6'',6'''-dimethoxy-4''''-methyl-1,1':4',1'':3'',1''':3''',1''''-quinquephenyl 
• 884010-31-5 2,2-dimethylpropane-1,3-diyl [2-methoxy-5-trimethylsilylethynylphenyl] boronate 
• 774608-07-0 4-(5-Bromo-2-hydroxy-phenyl)-6-chloro-pyrimidin-2-ylamine 
• 943917-69-9 (4R,5R)-3-[3,5-bis(trifluoromethyl)benzyl]-5-[5'-bromo-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]-4-methyl-1,3-oxazolidin-2-one 

Relevant academic research and scientific papers

Divergent synthesis of lamellarin α 13-sulfate, 20-sulfate, and 13,20-disulfate

A divergent synthesis of three sulfate derivatives of lamellarin α, namely, lamellarin α 13-sulfate (2), 20-sulfate (1), and 13,20-disulfate (4) has been achieved via a common intermediate (6) in which 13-OH and 20-OH of the lamellarin core are differentially protected by MOM and benzyl groups, respectively. Compound (6) in turn was prepared using sequential Suzuki-Miyaura coupling of 3,4-dihydroxypyrrole bistriflate (7) as a key reaction.

Facile Synthesis of 2-Bromo-3-fluorobenzonitrile: An Application and Study of the Halodeboronation of Aryl Boronic Acids

A scaleable synthesis of 2-bromo-3-fluorobenzonitrile via the NaOMe-catalyzed bromodeboronation of 2-cyano-6-fluorophenylboronic acid was developed. The generality of this transformation was demonstrated through the halodeboronation of a series of aryl boronic acids. Both aryl bromides and aryl chlorides were formed in good to excellent yields when the corresponding aryl boronic acid was treated with 1,3-dihalo-5,5-dimethylhydantoin and 5 mol % NaOMe.