99769-19-4

Basic information

• Product Name: 3-Methoxycarbonylphenylboronic acid
• Synonyms: METHYL 3-BORONOBENZOATE;3-METHOXYCARBONYLPHENYLBORONIC ACID;3-(METHOXYCARBONYL)BENZENEBORONIC ACID;AKOS BRN-0125;M-(METHOXYCARBONYL)PHENYLBORONIC ACID;3-METHOXYCARBONYLPHENYLBARONIC ACID;3-(Methoxycarbonyl)phenylboronic Acid (contains varying amounts of Anhydride);3-Methoxycarbonylphenylboronic acid,97%
• CAS NO: 99769-19-4
• Molecular Formula: C₈H₉BO₄
• Molecular Weight: 179.97
• Product Categories: blocks;BoronicAcids;Carboxes;Acids and Derivatives;Boron, Nitrile, Thio,& TM-Cpds;Boronic acids;Aryl;Ester;Organoborons;B (Classes of Boron Compounds);Boronic acid;CHIRAL CHEMICALS;Aromatics;Boron Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;Boronate Ester;Potassium Trifluoroborate
• Mol File: 99769-19-4.mol

Chemical Properties

• Melting Point: 205-208 °C(lit.)
• Boiling Point: 359.9 °C at 760 mmHg
• Flash Point: 171.5 °C
• Appearance: White to off-white/Powder
• Density: 1.25 g/cm³
• Vapor Pressure: 8.29E-06mmHg at 25°C
• Refractive Index: 1.532
• Storage Temp.: Refrigerator (+4°C)
• PKA: 7.74±0.10(Predicted)
• Water Solubility: Reacts with water.
• CAS DataBase Reference: 3-Methoxycarbonylphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methoxycarbonylphenylboronic acid(99769-19-4)
• EPA Substance Registry System: 3-Methoxycarbonylphenylboronic acid(99769-19-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 99769-19-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Methoxycarbonylphenylboronic acid is used as a key intermediate in the synthesis of substituted pyrazolylpyrimidinamine derivatives, which are known as protein kinase inhibitors. These inhibitors play a crucial role in the development of drugs targeting various diseases, including cancer and inflammatory conditions.
Used in Chemical Synthesis:
3-Methoxycarbonylphenylboronic acid is used as a reagent in the Suzuki reaction, a widely employed cross-coupling reaction for the formation of carbon-carbon bonds. This reaction is essential in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and natural products.
Used in Organic Chemistry Research:
3-Methoxycarbonylphenylboronic acid is utilized as a reagent in various organic reactions, such as tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence, copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides, one-pot ipso-nitration of arylboronic acids, and copper-catalyzed nitration. These reactions contribute to the development of new synthetic methods and the preparation of novel compounds with potential applications in various fields.
Used in Material Science:
3-Methoxycarbonylphenylboronic acid is employed in the preparation of biaryls via nickel-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl halides with arylboronic acid. This process is crucial in the synthesis of materials with unique properties, such as chromenones and their bradykinin B1 antagonistic active compounds, which have potential applications in drug discovery.
Used in Nanotechnology:
3-Methoxycarbonylphenylboronic acid is used in the synthesis of Pt nanoparticles at photoactive metal-organic frameworks, resulting in efficient hydrogen evolution via synergistic photoexcitation and electron injection. This application highlights the potential of 3-Methoxycarbonylphenylboronic acid in the development of advanced materials for energy conversion and storage.
Used in Biochemistry:
3-Methoxycarbonylphenylboronic acid is used in the synthesis of salicylate-based thienylbenzoic acids, which act as E. coli methionine aminopeptidase inhibitors. These inhibitors can be employed in the study of enzyme function and the development of new antimicrobial agents.

InChI:InChI=1/C8H9BO4/c1-13-8(10)6-3-2-4-7(5-6)9(11)12/h2-5,11-12H,1H3

Upstream product

• 67-56-1 methanol 
• 25487-66-5 3-Carboxyphenylboronic acid 
• 4518-10-9 Methyl 3-aminobenzoate 
• 13675-18-8 tetrahydroxydiboron 
• 618-89-3 methyl 3-bromobenzoate 
• 2905-65-9 methyl 3-chlorobenzoate 
• 618-91-7 methyl 3-iodo-benzoate 

Downstream Products

• 1033593-87-1 3-[4-((3R)-hydroxymethyl-3,4-dihydro-1H-isoquinolin-2-yl)-6-(4-methyl-piperazin-1-yl)-[1,3,5]triazin-2-yl]-benzoic acid methyl ester 
• 1044507-47-2 methyl 3-(oxetan-3-yl)benzoate 
• 1044507-46-1 isopropyl 3-(oxetan-3-yl)benzoate 
• 1138342-14-9 zinc(II) 5,10,15,20-tetrakis(3,5-di-tert-butylphenyl)-2-(3-methylbenzoate)porphyrin 
• 1266104-11-3 3-(9-oxo-5,7,8,9-tetrahydro-6H-xanthen-2-yl)benzoic acid methyl ester 
• 1335094-21-7 7-(3-carbomethoxyphenyl)-5-methyl-2-phenylbenzo[b]furan 
• 1335094-16-0 methyl 3-(2,5-diphenylbenzo[b]furan-7-yl)benzoate 
• 1335094-26-2 methyl 3-(5-fluoro-2-phenylbenzo[b]furan-7-yl)benzoate 
• 1221508-80-0 C₂₃H₁₉NO₃ 
• 1221509-55-2 C₂₁H₁₇NO₃S 
• 1228298-37-0 3-[6-(3,4-dichlorophenylamino)pyrimidin-4-yl]-benzoic acid methyl ester 
• 1203705-60-5 3-{[2-(3-methylcarboxyphenyl)pyrazolo[1,5-α]pyrimidin-7-yl]amino}phenol 
• 893736-81-7 3'-(methoxycarbonyl)biphenyl-3-carboxylic acid 
• 1200437-78-0 6-chloro-9-[3-(methoxycarbonyl)phenyl]purine 

Relevant articles and documents

Excellent quantum yield enhancement in luminescent metal-organic layer for sensitive detection of antibiotics in aqueous medium

Luminescent metal-organic layers (LMOLs) that can effectively improve fluorescence quantum yield and sensing performance are rarely reported. Herein, a novel tetracarboxyl-substituted tetraphenylethene (TPE) ligand 1,1,2,2-tetrakis[(3-carboxyphenyl)phenyl

Preparing methods of tetraphenylethylene-based carboxylic acid organic ligand and complexes of ligand

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Synthesis method for carbalkoxy phenylboronic acid

The invention relates to a synthesis method for carbalkoxy phenylboronic acid. Sulfoxide chloride is added into carboxy phenylboronic acid and alkyl alcohol, then a reflux reaction, cooling and filtering and high-temperature vacuum drying are carried out, then water is added, the mixture is stirred and then filtered, and carbalkoxy phenylboronic acid is obtained after room temperature drying. The synthesis method is easy and convenient to operate and high in yield, industrial production is easy to achieve, the market competitiveness of products of this kind is improved.

An easy route to (hetero)arylboronic acids

An unprecedented spontaneous reactivity between diazonium salts and diboronic acid has been unveiled, leading to a versatile arylboronic acid synthesis directly from (hetero)arylamines. This fast reaction (35 min overall) tolerates a wide range of functional groups and is carried out under very mild conditions. The radical nature of the reaction mechanism has been investigated.

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.

Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid

The Suzuki-Miyaura reaction has become one of the more useful tools for synthetic organic chemists. Until recently, there did not exist a direct way to make the most important component in the coupling reaction, namely the boronic acid. Current methods to make boronic acids often employ harsh or wasteful reagents to prepare boronic acid derivatives and require additional steps to afford the desired boronic acid. The scope of the previously reported palladium-catalyzed, direct boronic acid synthesis is unveiled, which includes a wide array of synthetically useful aryl electrophiles. It makes use of the newly available second generation Buchwald XPhos preformed palladium catalyst and bis-boronic acid. For ease of isolation and to preserve the often sensitive C-B bond, all boronic acids were readily converted to their more stable trifluoroborate counterparts.

Noncryogenic I/Br-Mg exchange of aromatic halides bearing sensitive functional groups using i-PrMgCl-Bis[2-(N,N-dimethylamino)ethyl] ether complexes

Iodo- and bromoaromatics bearing sensitive carboxylic ester and cyano groups underwent a selective halide-magnesium exchange with isopropylmagnesium chloride at ambient temperature in the presence of bis[2-(N,N-dimethylamino) ethyl] ether to afford the corresponding Grignard reagents. The newly formed reactive Grignard reagents were allowed to react with electrophiles such as trimethylborate to afford arylboronic acids in good to excellent yields.

A novel redox-sensitive protecting group for boronic acids, MPMP-diol

A new boronic acid protecting group, 1-(4-methoxyphenyl)-2-methylpropane-1, 2-diol (MPMP-diol), has been developed. Both protection and deprotection can be accomplished under mild conditions with quantitative conversions. The deprotection can be carried out using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).