13331-23-2

Basic information

• Product Name: 2-Furanboronic acid
• Synonyms: FURAN-2-BORONIC ACID;AKOS 90301;AKOS BRN-0264;2-FURYLBORONIC ACID;2-FURANBORONIC ACID;2-FURANYLBORONIC ACID;RARECHEM AH PB 0259;TIMTEC-BB SBB004326
• CAS NO: 13331-23-2
• Molecular Formula: C₄H₅BO₃
• Molecular Weight: 111.89
• EINECS: -0
• Product Categories: blocks;BoronicAcids;IndolesOxindoles;Heterocycles;Boronic acids;Boronic Acid;Furan;Organoborons;B (Classes of Boron Compounds);Boronic Acids;Boronic Acids and Derivatives;Heteroaryl;Boric Acid| Boric Acid Ester| Potassium Trifluoroborate
• Mol File: 13331-23-2.mol

Chemical Properties

• Melting Point: 112°C (dec.)
• Boiling Point: 247.7 °C at 760 mmHg
• Flash Point: 103.6 °C
• Appearance: Light beige/Crystalline Powder
• Density: 1.25 g/cm³
• Vapor Pressure: 0.0134mmHg at 25°C
• Refractive Index: 1.49
• Storage Temp.: Keep Cold
• Solubility: Chloroform (Slightly, Sonicated), DMSO (Slightly)
• PKA: 8.29±0.53(Predicted)
• Water Solubility: Slightly soluble in water.
• Sensitive: Air Sensitive
• BRN: 112370
• CAS DataBase Reference: 2-Furanboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Furanboronic acid(13331-23-2)
• EPA Substance Registry System: 2-Furanboronic acid(13331-23-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-3
• WGK Germany: 3
• HazardClass: IRRITANT, AIR SENSITIVE, KEEP CO
• Hazardous Substances Data: 13331-23-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Furanboronic acid is used as a key intermediate for the synthesis of various organic compounds, particularly in the Suzuki reaction. This reaction is a generalized route for the synthesis of β-furyl-α,β-unsaturated aldehydes, which are important building blocks in the creation of complex organic molecules.
Used in Pharmaceutical Industry:
2-Furanboronic acid is used as a building block for the development of novel pharmaceutical compounds. Its unique chemical structure allows for the creation of new drugs with potential applications in various therapeutic areas.
Used in Material Science:
2-Furanboronic acid is used as a component in the development of new materials with specific properties, such as improved strength, flexibility, or chemical resistance. Its incorporation into polymers and other materials can lead to enhanced performance in various applications.
Used in Research and Development:
2-Furanboronic acid is used as a research tool in the development of new chemical processes and methodologies. Its unique reactivity and properties make it an attractive candidate for exploring new synthetic routes and techniques in organic chemistry.

InChI:InChI=1/C4H5BO3/c6-5(7)4-2-1-3-8-4/h1-3,6-7H

Upstream product

• 121-43-7 Trimethyl borate 
• 2786-02-9 2-lithiofuran 
• 3187-94-8 2-chlorofuran 
• 110-00-9 furan 
• 5419-55-6 Triisopropyl borate 
• 531514-49-5 furan-2-ylmagnesium iodide 
• 1104637-62-8 2-(furan-2-yl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione 
• 166328-14-9 potassium (furan-2-yl)trifluoroboranuide 
• 7732-18-5 water 
• 584-12-3 2-bromofuran 
• 150-46-9 triethyl borate 
• 534-22-5 2-methylfuran 

Downstream Products

• 5857-37-4 2-furylmercuric chloride 
• 93349-97-4 Methyl 5-(2-Furyl)nicotinate 
• 127345-74-8 4-[4-methoxy-3-(furan-2-yl)phenyl]pyrrolidin-2-one 
• 142688-34-4 5-Furan-2-yl-3-pyridin-3-yl-1-(toluene-4-sulfonyl)-1H-indole 
• 190271-68-2 5-(furan-2-yl)-2-methoxybenzaldehyde 
• 182161-99-5 (5S,1'S)-N-[1'-(2-Furyl)-3'-phenylpropyl]-5-phenylmorpholin-2-one 
• 182161-97-3 (5S,1'S)-N-[1'-(2-Furyl)pentyl]-5-phenylmorpholin-2-one 
• 182162-03-4 (5S,1'S)-N-[1'-(2-furyl)-3',3'-dimethylbutyl]-5-phenylmorpholin-2-one 
• 182162-00-1 (5S,1'S)-N-[1'-(2-Furyl)-3',3'-dimethylbutyl]-5-phenylmorpholin-2-one 
• 182161-95-1 (5S,1'S)-N-[1'-(2-Furyl)butyl]-5-phenylmorpholin-2-one 

Relevant articles and documents

Gold(I)-Catalyzed Reactivity of Furan-ynes with N-Oxides: Synthesis of Substituted Dihydropyridinones and Pyranones

The reactivity of "furan-ynes"in combination with pyridine and quinoline N-oxides in the presence of a Au(I) catalyst, has been studied, enabling the synthesis of three different heterocyclic scaffolds. Selective access to two out of the three possible products, a dihydropyridinone and a furan enone, has been achieved through the fine-tuning of the reaction conditions. The reactions proceed smoothly at room temperature and open-air, and were further extended to a broad substrate scope, thus affording functionalized dihydropyridinones and pyranones.

Design and synthesis of furyl/thineyl pyrroloquinolones based on natural alkaloid perlolyrine, lead to the discovery of potent and selective PDE5 inhibitors

Based on perlolyrine (1), a natural alkaloid with weak PDE5 potency from the traditional Chinese aphrodisiac plant Tribulus terrestris L., a series α-substituted tetrahydro-β-carboline (THβC) derivatives were synthesized via T+BF4--mediated oxidative C–H functionalization of N-aryl THβCs with diverse potassium trifluoroborates. Following Winterfeldt oxidation afforded the corresponding furyl/thienyl pyrroloquinolones, of which 5-ethylthiophene/ethylfuran derivatives 20a–b were identified as the most potent and selective PDE5 inhibitors. Among the enantiomers, (S)-20a and (S)-20b (IC50 = 0.52 and 0.39 nM) were found to be more effective than their (R)-antipode, display favorable pharmacokinetic profiles, exert in vitro vasorelaxant effects on the isolated thoracic aorta, and exhibit in vivo efficacy in the anesthetized rabbit erectile model.

METALLOCENE COMPLEX AND OLEFIN POLYMERIZATION METHOD

Provided are a metallocene complex that facilitates copolymerization of olefin monomers including propylene at a higher uptake rate of comonomers, i.e., ethylene and α-olefin, manufacture of a rubber component having a higher molecular weight, and manufac

Organotrifluoroborate hydrolysis: Boronic acid release mechanism and an acid-base paradox in cross-coupling

The hydrolysis of potassium organotrifluoroborate (RBF3K) reagents to the corresponding boronic acids (RB(OH)2) has been studied in the context of their application in Suzuki-Miyaura coupling. The "slow release" strategy in such SM couplings is only viable if there is an appropriate gearing of the hydrolysis rate of the RBF3K reagent with the rate of catalytic turnover. In such cases, the boronic acid RB(OH)2 does not substantially accumulate, thereby minimizing side reactions such as oxidative homocoupling and protodeboronation. The study reveals that the hydrolysis rates (THF, H2O, Cs2CO 3, 55 °C) depend on a number of variables, resulting in complex solvolytic profiles with some RBF3K reagents. For example, those based on p-F-phenyl, naphthyl, furyl, and benzyl moieties are found to require acid catalysis for efficient hydrolysis. This acid-base paradox assures their slow hydrolysis under basic Suzuki-Miyaura coupling conditions. However, partial phase-splitting of the THF/H2O induced by the Cs2CO 3, resulting in a lower pH in the bulk medium, causes the reaction vessel shape, material, size, and stirring rate to have a profound impact on the hydrolysis profile. In contrast, reagents bearing, for example, isopropyl, β-styryl, and anisyl moieties undergo efficient "direct" hydrolysis, resulting in fast release of the boronic acid while reagents bearing, for example, alkynyl or nitrophenyl moieties, hydrolyze extremely slowly. Analysis of B-F bond lengths (DFT) in the intermediate difluoroborane, or the Swain-Lupton resonance parameter (R) of the R group in RBF3K, allows an a priori evaluation of whether an RBF3K reagent will likely engender "fast", "slow", or "very slow" hydrolysis. An exception to this correlation was found with vinyl-BF 3K, this reagent being sufficiently hydrophilic to partition substantially into the predominantly aqueous minor biphase, where it is rapidly hydrolyzed.

SLOW RELEASE OF ORGANOBORONIC ACIDS IN CROSS-COUPLING REACTIONS

A method of performing a chemical reaction includes reacting a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I) in a reaction mixture: R1-B-T; where R1 represents an organic group, T represents a conformationalIy rigid protecting group, and B represents boron having sp3 hybridization. When unprotected, the corresponding organoboronic acid is unstable by the boronic acid neat stability test. The reaction mixture further includes a base having a pKB of at least 1 and a pal ladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.

Solvent applications of 2-methyltetrahydrofuran in organometallic and biphasic reactions

2-Methyltetrahydrofuran (MeTHF) is a commercially available solvent that is produced from renewable resources. The properties of MeTHF place it between tetrahydrofuran (THF) and diethyl ether in solvent polarity and Lewis base strength. In many cases, MeTHF can replace THF in organometallic reactions. The formation and reaction of Grignard reagents in MeTHF and THF are similar. MeTHF can be used as a solvent for low-temperature lithiation, for lithium aluminum hydride reductions, for the Reformatsky reaction, and for metal-catalyzed coupling reactions. MeTHF is also a good substitute for dichloromethane in biphasic reactions.

COMPOUNDS, COMPOSITIONS AND METHODS

The present invention provides methods and pharmaceutical compositions for inhibiting expressions of HIF and HIF regulated genes, inhibiting angiogenesis, inducing cell cycle arrest in tumor cells, and treating cell proliferating diseases or conditions.

METHOD FOR METAL-ORGANIC PRODUCTION OF ORGANIC INTERMEDIATE PRODUCTS BY MEANS OF ARYL LITHIUM-BASES

The invention relates to a method for the production of substituted aromatic compounds by producing lithium arylene and by reacting it with suitable electrophiles. The method comprises the following steps (step 1); an aryl lithium compound ( auxiliary base'') is initially produced by reacting a halogen aromatic compound with lithium metal; said compound is subsequently (step 2) reacted for deprotonation of the aromatic substrate in order to form the corresponding lithium aromatic compound which is subsequently (step 3) reacted with a corresponding electrophile to form the desired substituted aromatic compound, see page 2 of the description.

Process for preparing boronic and borinic acids

A process for preparing boronic acids of the formula (I) and borinic acids of the formula (II), by reaction of chloroaromatics of the formula (III) with lithium metal and boron compounds BW′W′W′″, where W′, W′ and W′″ are each, independently of one another, C1-C6-alkoxy, fluorine, chlorine, bromine, iodine, N(C1-C6-alkyl)2 or S(C1-C5-alkyl), in a solvent at temperatures in the range from ?100 to 80° C.