5467-74-3

Basic information

• Product Name: 4-Bromophenylboronic acid
• Synonyms: 4-BROMOPHENYLBORIC ACID ANHYDRIDE;4-BROMOPHENYLBORONIC ACID;4-BROMOBENZENEBORONIC ACID;4-BROMOBENZENEBORONIC ACID/ANHYDRIDE;AKOS BRN-0005;RARECHEM AH PB 0075;P-BROMO BENZENE BORONIC ACID;P-BROMOPHENYLBORONIC ACID
• CAS NO: 5467-74-3
• Molecular Formula: C₆H₆BBrO₂
• Molecular Weight: 200.83
• EINECS: 226-779-9
• Product Categories: blocks;BoronicAcids;Bromides;Boric Acid;Substituted Boronic Acids;Boronic acids;Boronic Acid;Aryl;Halogenated;Organoborons;B (Classes of Boron Compounds);OLED materials,pharm chemical,electronic;Boronate Ester;Potassium Trifluoroborate
• Mol File: 5467-74-3.mol

Chemical Properties

• Melting Point: 284-288 °C(lit.)
• Boiling Point: 315 °C at 760 mmHg
• Flash Point: 144.3 °C
• Appearance: Off-white to light beige/Crystalline Powder
• Density: 1.67 g/cm³
• Vapor Pressure: 0.00019mmHg at 25°C
• Refractive Index: 1.598
• Storage Temp.: 0-6°C
• PKA: 8.32±0.10(Predicted)
• Water Solubility: Soluble in methanol. Insoluble in water.
• BRN: 2936347
• CAS DataBase Reference: 4-Bromophenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromophenylboronic acid(5467-74-3)
• EPA Substance Registry System: 4-Bromophenylboronic acid(5467-74-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: CY8650000
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 5467-74-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
4-Bromophenylboronic acid is used as a reagent for palladium-catalyzed Suzuki-Miyaura cross-couplings, a widely employed method for the formation of carbon-carbon bonds. This reaction is crucial in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and advanced materials.
Used in Tandem Reactions:
4-Bromophenylboronic acid is utilized in tandem-type Pd(II)-catalyzed oxidative Heck reactions and intramolecular C-H amidation sequences. These reactions enable the efficient construction of complex molecular architectures, which are valuable in the development of new drugs and functional materials.
Used in Medicinal Chemistry:
4-Bromophenylboronic acid is employed in the preparation of protein modulators, enzymatic and kinase inhibitors, and gallate-based obovatol analogs with potential anti-tumor activity. These compounds are essential in the discovery and development of novel therapeutic agents for the treatment of various diseases.
Used in Fluoroalkylation Reactions:
4-Bromophenylboronic acid is used as a reagent for copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides. This reaction allows for the introduction of fluoroalkyl groups into organic molecules, which can improve their pharmacological properties, such as lipophilicity and metabolic stability.
Used in Cyclization Reactions:
4-Bromophenylboronic acid is utilized in Pd-catalyzed arylative cyclization of alkyne-tethered enals or enones via carbopalladation of alkynes. This reaction provides a convenient method for the synthesis of cyclic compounds, which are often found in biologically active natural products and pharmaceutical agents.
Used in Copper-Catalyzed Cross-Couplings:
4-Bromophenylboronic acid is employed in copper-catalyzed cross-couplings, which are useful for the formation of carbon-carbon and carbon-heteroatom bonds. These reactions contribute to the synthesis of diverse organic compounds, including those with potential applications in materials science and medicinal chemistry.
Used in Enzyme Inhibition:
Labelled 4-Bromophenylboronic acid (B686545) is used in the preparation of arylboronates as inhibitors of fatty acid amide hydrolase. These inhibitors can help researchers study the role of this enzyme in various biological processes and may lead to the development of new therapeutic agents for the treatment of related disorders.

InChI:InChI=1/C6H6BBrO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H

Upstream product

• 13195-76-1 triisobutyl borate 
• 18620-02-5 (4-bromophenyl)magnesium bromide 
• 688-74-4 boric acid tributyl ester 
• 96484-29-6 bis(4-bromophenyl)borinic acid 
• 108-86-1 bromobenzene 
• 7519-94-0 2,4,6-tris(4-bromophenyl)boroxin 
• 106-37-6 1.4-dibromobenzene 
• 589-87-7 1,4-bromoiodobenzene 
• 121-43-7 Trimethyl borate 
• 13283-31-3 borane 
• 374564-35-9 potassium 4-bromophenyltrifluoroborate 
• 13675-18-8 tetrahydroxydiboron 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 106-40-1 4-bromo-aniline 

Downstream Products

• 115247-41-1 4-bromobenzeneboronic acid N-methyldiethanolamine cyclic ester 
• 7519-94-0 2,4,6-tris(4-bromophenyl)boroxin 
• 74386-13-3 4-bromo-3-nitrophenylboronic acid 
• 19719-72-3 bis-(4-bromo-phenyl)-mercury 
• 5493-08-3 2-(4-bromo-phenyl)-[1,3,6,2]dioxazaborocane 
• 96983-22-1 (4-bromo-phenyl)-boronic acid dibutyl ester 
• 54947-90-9 2-(4-bromophenyl)[1,3,2]dioxaborolane 
• 54947-91-0 4-bromophenylboronic acid 
• 51310-29-3 methyl 4-(4-bromobenzoyl)benzoate 
• 130163-33-6 2-(4-Bromo-phenyl)-7-methoxy-cyclohepta-2,4,6-trienone 
• 129921-03-5 (E)-1-(4-bromophenyl)-1-<4-(2-chloroethoxy)phenyl>-2-phenyl-1-butene 
• 129921-03-5 (Z)-1-(4-bromophenyl)-1-<4-(2-chloroethoxy)phenyl>-2-phenyl-1-butene 
• 145297-34-3 4-(4-Bromophenyl)-8-methoxy-5-nitroquinoline 
• 460-00-4 1-Bromo-4-fluorobenzene 

Relevant articles and documents

Preparation method of monohalogenated phenylboronic acid

The invention relates to the technical field of chemical synthesis, and particularly discloses a preparation method of monohalogenated phenylboronic acid. The preparation method comprises the following steps of: by taking dihalogenated benzene as a raw material and a mixture of lithium salt and alkaline ionic liquid as a catalyst, carrying out Grignard exchange with R1MgCl to generate monohalogenated phenyl magnesium chloride, reacting with B (OR) 3 to generate monohalogenated phenyl borate, and hydrolyzing under acidic conditions to obtain monohalogenated phenylboronic acid. The HPLC (High Performance Liquid Chromatography) content of the monohalogenated phenylboronic acid prepared by the method is greater than 99.5%; the total yield of the product is greater than 80%, the contents of monohalogenated phenylboronic acid and phenyldiboronic acid impurities of another halogen are both less than 0.003%, the requirements of modern fine chemical synthesis are completely met, the raw materials are easily available, the operation is simple, the safety is high, and the industrial production of monohalogenated phenylboronic acid is realized.

Ligand-Less Iron-Catalyzed Aromatic Cross-Coupling Difluoromethylation of Grignard Reagents with Difluoroiodomethane

Iron-catalyzed cross-coupling difluoromethylations of the Grignard reagents with difluoroiodomethane provide various aromatic difluoromethyl products in good yields, not employing sterically demanding ligands. Difluoromethylations proceed within 30 min at -20 °C with 2.0 equiv of the Grignard reagents and FeCl3 or Fe(acac)3 (2.5 mol %). Mechanistic investigations clarify difluoromethyl radical intervention; Fe(0) ate is initially generated. Single-electron transfer from Fe(0) ate to difluoroiodomethane takes place. Recombination with aryl groups gives Ar-CF2Hs. The catalyst can be regenerated by the Grignard reagents.

A novel graphite-like stacking structure in a discrete molecule and its molecular recognition behavior

A graphite-like stacking structure was nicely reproduced in a discrete molecule that was prepared by 2+2 macrocyclic Schiff base formation. In the crystal structure, two hexabenzocoronene planes are closely stacked with displacement, yielding the intramolecular stacking structure similar to an AB- or ABC-stacking pattern in natural graphite. This molecule showed a recognition ability toward electron-deficient aromatic molecules in solution.

An efficient method for the hydrolysis of potassium organotrifluoroborates promoted by montmorillonite K10

An efficient and non-expensive method for conversion of diverse potassium organotrifluoroborates to their corresponding boronic acids promoted by montmorillonite K10 using water as the reaction solvent is described. Further interconversion of potassium organotrifluoroborates to their corresponding boronic esters, via boronic acid intermediates was also successfully accomplished. The products were obtained in good yields, being the rate of hydrolysis influenced by the type of substituent present in the boronic acid.

Flow Chemistry on Multigram Scale: Continuous Synthesis of Boronic Acids within 1 s

The benefits and limitations of a simple continuous flow setup for handling and performing of organolithium chemistry on the multigram scale is described. The developed metalation platform embodies a valuable complement to existing methodologies, as it combines the benefits of Flash Chemistry (chemical synthesis on a time scale of 1 s) with remarkable throughput (g/min) while mitigating the risk of blockages.

Asymmetric Arylation of Imines Catalyzed by Heterogeneous Chiral Rhodium Nanoparticles

Asymmetric arylation of aldimines catalyzed by heterogeneous chiral rhodium nanoparticles has been developed. The reaction proceeded in aqueous media without significant decomposition of the imines by hydrolysis to afford chiral (diarylmethyl)amines in high yields with outstanding enantioselectivities. This catalyst system exhibited the highest turnover number (700) in heterogeneous catalysts reported to date for these reactions. The reusability of the catalyst was also demonstrated.

Novel organic semiconductor compound and organic light emitting device using the same

The present invention relates to a novel organic semiconductor compound, and an organic electroluminescent device using the same. More particularly, the organic semiconductor compound according to the present invention is an azasiline derivative with a rigid structure having an electron doner and an electron acceptor in the molecule, and can embody excellent oxidation stability and light emitting characteristics. The organic electroluminescent device using the same has a high purity blue color having high quantum efficiency. The organic semiconductor compound is represented by chemical formula 1.

Phototautomerization in Pyrrolylphenylpyridine Terphenyl Systems

[4-(2-Pyrrolyl)phenyl]pyridines 2-4 were synthesized and their photophysical properties and reactivity in phototautomerization reactions investigated by fluorescence spectroscopy and laser flash photolysis (LFP). The pKa for the protonation of the pyridine nitrogen in 2-4 was determined by UV-vis and fluorescence titration (pKa = 5.5 for 4). On excitation in polar protic solvents, 2-4 populate charge-transfer states leading to an enhanced basicity of the pyridine (pKa? ≈ 12) and enhanced acidity of pyrrole (pKa? ≈ 8-9) enabling excited-state proton transfer (ESPT). ESPT gives rise to phototautomers and significantly quenches the fluorescence of 2-4. Phototautomers 2-T and 4-T were detected by LFP with strong transient absorption maxima at 390 nm. Phototautomers 2-T and 4-T decayed by competing uni- and bimolecular reactions. However, at pH 11 the decay of 4-T followed exponential kinetics with a rate constant of 4.2 × 106 s-1. The pyridinium salt 4H+ forms a stable complex with cucurbit[7]uril (CB[7]) with 1:1 stoichiometry (β11 = (1.0 ± 0.2) × 105 M-1, [Na+] = 39 mM). Complexation to CB[7] increased the pKa for 4H+ (pKa = 6.9) and changed its photochemical reactivity. Homolytic cleavage of the pyrrole NH leads to the formation of an N-radical because of the decreased acidity of the pyrrole in the inclusion complex. (Figure Presented).

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF

The present invention provides a novel compound capable of improving light emitting efficiency, stability and lifespan of an element, an organic electronic element using the same and an electronic device thereof.(110) Substrate(120) Positive electrode(130) Hole injection layer(140) Hole transfer layer(141) Buffer layer(150) Light emitting layer(151) Light-emitting assisting layer(160) Electron transfer layer(170) Electron injection layer(180) Negative electrodeCOPYRIGHT KIPO 2016

Methanol-promoted borylation of arylamines: A simple and green synthetic method to arylboronic acids and arylboronates

A Sandmeyer borylation of arylamines via a SN2Ar pathway promoted by methanol with sodium nitrite and hydrochloric acid as diazotization agent has been developed, which provide a simple and green synthetic method to arylboronic acids and arylboronates. Georg Thieme Verlag Stuttgart New York.