87199-16-4

Basic information

• Product Name: 3-Formylphenylboronic acid
• Synonyms: 3-Formylpenylboronic Acid;Boronic acid, (3-formylphenyl)- (9CI);3-FORMYLPHENYLBORONIC ACID (CONTAINS VARYING AMOUNTS OF ANHYDRIDE);3-(Dihydroxyboryl)benzaldehyde, 3-Boronobenzaldehyde;3-Formylphenylboronic acid,97%;2-bromo-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)ethanone;3-Formylphenylboronic acid, May contain varying amounts of anhydride, 97%;3-Formylphenylboroni
• CAS NO: 87199-16-4
• Molecular Formula: C₇H₇BO₃
• Molecular Weight: 149.94
• EINECS: 628-589-5
• Product Categories: ALDEHYDE;Aldehydes;blocks;BoronicAcids;Boronic Acid series;Boron, Nitrile, Thio,& TM-Cpds;Carbonyl Compounds;Substituted Boronic Acids;Boronic Acids & Esters;Phenyls & Phenyl-Het;Boronic acids;Boronic Acid;Aryl;Organoborons;B (Classes of Boron Compounds);Boronic Acids & Esters;Phenyls & Phenyl-Het;Aryl Boronic Acids;Boronic Acids and Derivatives;Building Blocks;C7;Chemical Synthesis;Monosubstituted Aryl Boronic Acids;Organic Building Blocks;Organometallic Reagents;Boronate Ester;Potassium Trifluoroborate
• Mol File: 87199-16-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 182-186 °C
• Boiling Point: 354.388 °C at 760 mmHg
• Flash Point: 168.128 °C
• Appearance: Off-white to beige or light orange/Powder, Crystals, and/or Chunks
• Density: 1.244 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.548
• Storage Temp.: 0-6°C
• Solubility: soluble in Methanol
• PKA: 7.83±0.10(Predicted)
• Sensitive: Air Sensitive
• BRN: 3030769
• CAS DataBase Reference: 3-Formylphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Formylphenylboronic acid(87199-16-4)
• EPA Substance Registry System: 3-Formylphenylboronic acid(87199-16-4)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 22-26-36/37/39-45-37/39-27
• RIDADR: UN 3261 8/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT, MOISTURE SENSITIVE
• PackingGroup: Ⅲ
• Hazardous Substances Data: 87199-16-4(Hazardous Substances Data)

Usage

Description

3-Formylphenylboronic acid is an organic compound that features a boronic acid group attached to a formyl-substituted phenyl ring. It is known for its unique chemical properties and reactivity, making it a versatile molecule in various chemical and biological applications.

Uses

Used in Chemical Research:
3-Formylphenylboronic acid is used as a reagent to study the effects of boronic acid on fluoride-selective chemosignaling behavior of merocyanine dye. This application is crucial for understanding the interactions between boronic acids and other chemical species, which can be instrumental in developing new sensors and materials.
Used in Biophysical Studies:
As exciton-coupled CD probes for epigallocatechin gallate, 3-Formylphenylboronic acid aids in the investigation of molecular interactions and conformational changes in biological systems. This use is valuable for advancing our knowledge of biomolecular structures and their functions.
Used in Enzyme Inhibition:
3-Formylphenylboronic acid serves as a biological inhibitor of γ-glutamyltranspeptidase, an enzyme involved in the metabolism of glutathione. Its inhibitory action can be harnessed in the development of therapeutic agents targeting specific metabolic pathways.
Used in Organic Synthesis:
In the field of organic synthesis, 3-Formylphenylboronic acid is utilized as a reactant in palladium-catalyzed homocoupling reactions. This process allows for the formation of biaryl compounds, which are important structural motifs in pharmaceuticals and agrochemicals.
Used in Cross-Coupling Reactions:
3-Formylphenylboronic acid is a key component in Suzuki coupling reactions, a widely used cross-coupling method for the formation of carbon-carbon bonds. This reaction is essential for the synthesis of complex organic molecules and the development of new chemical entities.

InChI:InChI=1/C7H7BO3/c9-5-6-2-1-3-7(4-6)8(10)11/h1-5,10-11H

Upstream product

• 112626-62-7 (3-dibromomethyl-phenyl)-dihydroxy-borane 
• 68578-52-9 3-chlorobenzaldehyde diethyl acetal 
• 17933-03-8 m-tolylboronic acid 
• 5419-55-6 Triisopropyl borate 
• 3132-99-8 m-bromobenzoic aldehyde 
• 68-12-2 N,N-dimethyl-formamide 
• 98527-70-9 tris(3-bromo phenyl)boroxine 
• 480424-60-0 C₉H₁₁BO₄ 
• 79421-98-0 2,4,6-tris(m-tolyl)boroxine 
• 17789-14-9 3-(1,3-dioxolan-2-yl)-phenylbromide 

Downstream Products

• 478930-25-5 3-[1,3,2]Dioxaborinan-2-yl-benzaldehyde 
• 362052-27-5 3-(3-methylpyridin-2-yl)benzaldehyde 
• 263349-22-0 3-(pyrimidin-2-yl)benzaldehyde 
• 283147-95-5 4'-hydroxy-[1,1'-biphenyl]-3-carbaldehyde 
• 85553-52-2 3-(furan-2-yl)benzaldehyde 

Relevant articles and documents

Copper-Catalyzed Monoorganylation of Trialkyl Borates with Functionalized Organozinc Pivalates

Organozinc pivalates, a recently developed air- and moisture-stable organozinc species, were found for the first time as excellent organometallic species in the monoorganylation of trialkyl borates whereby boronic acids were prepared in high yields. The significant advantage of organozinc pivalates over another previously employed organometallic reagents, e. g., organolithium reagents, Grignard reagents and organozinc halides, is that the generation of multiorganylation byproducts such as borinic acids and trialkylboranes were completely suppressed. Additionally, the in situ generated boronates could be directly arranged into Suzuki-Miyaura type cross-coupling reactions to produce biaryls in high yields.

A process for preparing aldehyde group benzene boric acid

The invention discloses a method for preparing formyl phenylboronic acid, which comprises the following steps: heating halogenated phenylboronic acid in toluene or heptane under reflux for dewatering to form a tripolymer, mixing the tripolymer with dimethylformamide, dropwisely adding n-butyllithium at low temperature to react by a one-pot process, hydrolyzing with hydrochloric acid, and recrystallizing to obtain the formyl phenylboronic acid. The method is simple to operate, avoids the process of separating the intermediate after formyl protection in the conventional technique, has high universality, can obtain favorable yield for ortho-, meta- and para- formyl phenylboronic acids, and is beneficial to scale-up production.

Palladium-catalyzed borylation of aryl and heteroaryl halides utilizing tetrakis(dimethylamino)diboron: One step greener

The palladium-catalyzed borylation of aryl and heteroaryl halides with a novel borylating agent, tetrakis(dimethylamino)diboron [(Me2N) 2B-B(NMe2)2], is reported. The method is complementary to the previously reported method utilizing bis-boronic acid (BBA) in that certain substrates perform better under one set of optimized reaction conditions than the other. Because tetrakis(dimethylamino)diboron is the synthetic precursor to both BBA and bis(pinacolato)diboron (B 2Pin2), the new method represents a more atom-economical and efficient approach to current borylation methods.