374538-03-1

Basic information

• Product Name: 2-Methoxycarbonylphenylboronic acid
• Synonyms: METHYL 2-BORONOBENZOATE;2-(METHOXYCARBONYL)BENZENEBORONIC ACID;2-METHOXYCARBONYLPHENYLBORONIC ACID;O-(METHOXYCARBONYL)PHENYLBORONIC ACID;Benzoic acid, 2-borono-, 1-methyl ester (9CI);2-Carbomethoxybenzeneboronicacid;2-(Methoxycarbonyl)Phenylboron;2-(Methoxycarbonyl)phenylboronic Acid (contains varying amounts of Anhydride)
• CAS NO: 374538-03-1
• Molecular Formula: C₈H₉BO₄
• Molecular Weight: 179.97
• Product Categories: BORONICACID;blocks;BoronicAcids;Carboxes;Boronic acids;B (Classes of Boron Compounds);Aryl;Boronic Acids;Boronic Acids and Derivatives;Aryl Boronic Acids;Boronic Acids and Derivatives;Chemical Synthesis;Monosubstituted Aryl Boronic Acids;Organometallic Reagents;Boronate Ester;Boronic Acid;Potassium Trifluoroborate
• Mol File: 374538-03-1.mol

Chemical Properties

• Melting Point: 90-96°C
• Boiling Point: 359 °C at 760 mmHg
• Flash Point: 170.9 °C
• Appearance: White/Crystalline Powder
• Density: 1.25 g/cm³
• Vapor Pressure: 8.89E-06mmHg at 25°C
• Refractive Index: 1.532
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: soluble in Methanol
• PKA: 8.19±0.58(Predicted)
• BRN: 8313459
• CAS DataBase Reference: 2-Methoxycarbonylphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxycarbonylphenylboronic acid(374538-03-1)
• EPA Substance Registry System: 2-Methoxycarbonylphenylboronic acid(374538-03-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• TSCA: No
• HazardClass: IRRITANT
• Hazardous Substances Data: 374538-03-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Methoxycarbonylphenylboronic acid is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a versatile building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-Methoxycarbonylphenylboronic acid serves as a valuable reagent for the preparation of various organic compounds. Its boronic acid group enables it to participate in a range of chemical reactions, making it a useful component in the synthesis of complex organic molecules.
Used in Material Science:
2-Methoxycarbonylphenylboronic acid is also utilized in material science for the development of new materials with specific properties. Its ability to form stable bonds with other molecules allows it to be incorporated into the design of advanced materials with potential applications in various industries.

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

Upstream product

• 7647-01-0 hydrogenchloride 
• 5419-55-6 Triisopropyl borate 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 610-96-8 methyl chlorobenzoate 
• 610-97-9 o-iodo-methyl-benzoic acid 

Downstream Products

• 606-28-0 methyl o-benzoylbenzoate 
• 116664-93-8 sampangine 
• 87-41-2 2-benzofuran-1(3H)-one 
• 1616729-76-0 methyl 2-(benzo[d]thiazol-2-yldifluoromethyl)benzoate 
• 1616729-68-0 methyl 2-(difluoro(5-methylbenzo[d]oxazol-2-yl)methyl)benzoate 

Relevant articles and documents

Method for synthesizing sodium 2-carboxyphenylborate

The invention discloses a method for synthesizing sodium 2-carboxyphenylborate. The method comprises the following two steps of: 1) taking methyl 2-bromobenzoate as an initial raw material, through bromine removal by butyl lithium, carrying out a one-pot reaction with triisopropyl borate or trimethyl borate to obtain a product 2-methoxycarbonyl phenylboronic acid, and 2) hydrolyzing the 2-methoxycarbonyl phenylboronic acid in a sodium hydroxide methanol solution, and pulping with acetone to obtain sodium 2-carboxyphenylborate monohydrate. The method has the advantages of easily available raw materials, simple operation, safety, environmental protection, low cost and high yield.

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.