89598-96-9

Basic information

• Product Name: 3-Bromophenylboronic acid
• Synonyms: RARECHEM AH PB 0076;AKOS BRN-0083;3-BROMOBENZENEBORONIC ACID;3-BROMOPHENYLBORONIC ACID;3-Bromophenylboronic;3-Bromobenzeneboronic acid, 98+%;3-Bromophenylboronic Acid (contains varying amounts of Anhydride);3-Bromophenylboronic acid,97%
• CAS NO: 89598-96-9
• Molecular Formula: C₆H₆BBrO₂
• Molecular Weight: 200.83
• EINECS: 1312995-182-4
• Product Categories: blocks;BoronicAcids;Bromides;Boric Acid;Boronic acids;Boronic Acid;Aryl;Organoborons;B (Classes of Boron Compounds);Boronic Acids;Boronic Acids and Derivatives;Aryl Boronic Acids;Boronic Acids and Derivatives;Chemical Synthesis;Monosubstituted Aryl Boronic Acids;Organometallic Reagents;Boronate Ester;Potassium Trifluoroborate
• Mol File: 89598-96-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 164-168 °C(lit.)
• Boiling Point: 330.5 °C at 760 mmHg
• Flash Point: 153.7 °C
• Appearance: White/Crystalline Powder
• Density: 1.67 g/cm³
• Vapor Pressure: 6.63E-05mmHg at 25°C
• Refractive Index: 1.598
• Storage Temp.: 0-6°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 7.55±0.10(Predicted)
• BRN: 3127104
• CAS DataBase Reference: 3-Bromophenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromophenylboronic acid(89598-96-9)
• EPA Substance Registry System: 3-Bromophenylboronic acid(89598-96-9)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 37/39-26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 89598-96-9(Hazardous Substances Data)

Usage

Description

3-Bromophenylboronic acid is an organic compound that features a boron atom bonded to a phenyl group with a bromine atom attached at the 3-position. It is a versatile reagent in organic synthesis, known for its stability and reactivity in various chemical reactions.

Uses

Used in Pharmaceutical Industry:
3-Bromophenylboronic acid is used as a reactant in the synthesis of pharmaceutical compounds, particularly for the development of new drugs and the modification of existing ones. Its reactivity allows for the formation of new chemical bonds and the creation of diverse molecular structures.
Used in Chemical Research:
3-Bromophenylboronic acid is used as a reactant in a variety of organic reactions for the advancement of chemical research. Its applications include:
1. Oxidative cross coupling: It serves as a key reactant in oxidative cross-coupling reactions, enabling the formation of carbon-carbon bonds and the synthesis of complex organic molecules.
2. Gold salt catalyzed homocoupling: It is utilized in gold salt-catalyzed homocoupling reactions, which facilitate the formation of carbon-carbon bonds through the coupling of two identical molecules.
3. 1,4-Addition reactions with α,β-unsaturated ketones: It participates in 1,4-addition reactions with α,β-unsaturated ketones, leading to the formation of new carbon-carbon bonds and the synthesis of various organic compounds.
4. Enantioselective addition reactions: It is employed in enantioselective addition reactions, which allow for the selective formation of one enantiomer over another, contributing to the development of chiral molecules with specific biological activities.
5. Suzuki-Miyaura coupling: It is used in Suzuki-Miyaura coupling reactions for the synthesis of anthranilamide-protected arylboronic acids, which are important intermediates in the production of pharmaceuticals and other organic compounds.
6. C-H Functionalization of quinones: It is involved in the C-H functionalization of quinones, a reaction that allows for the modification of quinone structures, leading to the development of new compounds with potential applications in various industries.
Overall, 3-Bromophenylboronic acid is a valuable reagent in the fields of pharmaceuticals, chemical research, and organic synthesis, playing a crucial role in the development of new compounds and the advancement of chemical knowledge.

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

Upstream product

• 150-46-9 triethyl borate 
• 108-36-1 1,3-dibromobenzene 
• 108-37-2 1-bromo-3-chlorobenzene 
• 121-43-7 Trimethyl borate 
• 591-18-4 1-Bromo-3-iodobenzene 
• 7732-18-5 water 
• 5419-55-6 Triisopropyl borate 
• 688-74-4 boric acid tributyl ester 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 423775-08-0 (E)-n-butyl 3-(3-bromophenyl)acrylate 
• 4373-60-8 2-(3-bromophenyl)pyridine 
• 137481-74-4 3-methylsulfonyl-6-(morpholin-4-yl)-1,2,4,5-tetrazine 
• 914262-89-8 7-(3-bromophenyl)-2-cyanonaphthalene 
• 638218-61-8 8-(3-bromo-phenyl)-6-(1-methanesulfonyl-1-methyl-ethyl)-quinoline 
• 668438-44-6 5-bromo-2-(3'-bromophenyl)pyridine 
• 897948-14-0 C₁₈H₂₂BrNO₄ 
• 1016-77-9 3-bromobenzophenone 
• 872965-18-9 9,10-bis(3-bromophenyl)anthracene 
• 1279015-31-4 (S)-2-(3'-cyclopropylbiphenyl-4-yloxymethyl)-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one 
• 1298131-40-4 2-(3-(3-bromophenyl)prop-2-yn-1-yl)isoindoline-1,3-dione 
• 1298131-47-1 N-benzyl-2-(3-bromophenylthio)benzamide 
• 1340545-15-4 C₂₅H₁₉Br 
• 37831-25-7 N-(3-bromophenyl)formamide 

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.

Effective Utilization of Flow Chemistry: Use of Unstable Intermediates, Inhibition of Side Reactions, and Scale-Up for Boronic Acid Synthesis

Flow chemistry processes for boronic acid syntheses utilizing lithiation-borylation have been developed. The side reactions in the lithiation step that occur in batch were suppressed, and unstable lithium intermediates were handled safely. Flow technology was applied to several kinds of boronic acid syntheses, and scale-up was successfully conducted to allow kilogram-scale production. Some of the key benefits of flow flash chemistry were utilized, both to avoid side reactions and to enable dianion chemistry that is difficult to perform successfully in batch reactions. The examples showed further perspectives on the utility of flow technologies for process development.

Metal complex containing carbazoles connected Phenyl-pyridine, it's preparation method and it's applications

PURPOSE: A phenyl-pyridine metal complex compound which is connected with carbazole structure is provided to enhance high electroluminescence(EL) intensity at 700-750 nm. CONSTITUTION: A metal complex compound contains a phenylpyridine structure which is connected with carbazole structure of chemical formula 1. In chemical formula 1, M is metal having an atom weight of 40 or more; X-Y is auxiliary ligand; R1 is alkyl of 1-16 carbon atoms or alkyl ether group of 1-16 carbon atoms; and R2 and R3 are F or CF_3 each. A light emitting device contains the metal complex compound. A sensor is manufactured using the light emitting device.