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
• Article Data: 22

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

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 5467-74-3 differently. You can refer to the following data:
1. suzuki reaction
2. 4-Bromobenzeneboronic acid is a reagent used for Palladium catalyzed Suzuki-Miyaura cross-couplings, Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence. It is also used in the preparation of Protein modulators and enzymatic and kinase inhibitors, Gallate-based obovatol analogs with potential anti-tumor activity. It is used as a reagent for Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides, Pd-catalyzed arylative cyclization of alkyne-tethered enals or enones via carbopalladation of alkynes, Copper-catalyzed cross-couplings.
3. Labelled 4-Bromophenylboronic Acid (B686545). 4-Bromophenylboric acid is used in the preparation of arylboronates as inhibitors of fatty acid amide hydrolase.

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

Upstream product

• 96484-29-6 bis(4-bromophenyl)borinic acid 
• 108-86-1 bromobenzene 
• 121-43-7 Trimethyl borate 
• 106-37-6 1.4-dibromobenzene 
• 13283-31-3 borane 
• 18620-02-5 (4-bromophenyl)magnesium bromide 
• 374564-35-9 potassium 4-bromophenyltrifluoroborate 
• 589-87-7 1,4-bromoiodobenzene 
• 150-46-9 triethyl borate 
• 5419-55-6 Triisopropyl borate 
• 106-39-8 bromochlorobenzene 
• 7732-18-5 water 
• 106-40-1 4-bromo-aniline 
• 13675-18-8 tetrahydroxydiboron 

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.

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.

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.