55552-70-0

Basic information

• Product Name: 3-Furanboronic acid
• Synonyms: FURAN-3-BORONIC ACID;3-FURYLBORONIC ACID;3-FURANBORONIC ACID;3-FURANYLBORONIC ACID;TIMTEC-BB SBB004327;RARECHEM AH PB 0244;3-Furylboronic acid (contains varying amounts of anhydride);furan-3-ylboronic acid
• CAS NO: 55552-70-0
• Molecular Formula: C₄H₅BO₃
• Molecular Weight: 111.89
• EINECS: -0
• Product Categories: blocks;BoronicAcids;Heterocycles;Boronic acids;Boronic acid;Furan;Organoborons;B (Classes of Boron Compounds);Boronic Acids;Boronic Acids and Derivatives;Heteroaryl;Boronic Acids and Derivatives;Chemical Synthesis;Heteroaryl Boronic Acids;Organometallic Reagents
• Mol File: 55552-70-0.mol

Chemical Properties

• Melting Point: 139-144 °C (dec.)(lit.)
• Boiling Point: 247.7 °C at 760 mmHg
• Flash Point: 103.6 °C
• Appearance: Yellow/Crystalline Powder
• Density: 1.25 g/cm³
• Vapor Pressure: 0.0134mmHg at 25°C
• Refractive Index: 1.49
• Storage Temp.: 0-6°C
• Solubility: Soluble in methanol.
• PKA: 7.95±0.10(Predicted)
• BRN: 1635653
• CAS DataBase Reference: 3-Furanboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Furanboronic acid(55552-70-0)
• EPA Substance Registry System: 3-Furanboronic acid(55552-70-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-3-37
• WGK Germany: 3
• HazardClass: IRRITANT, AIR SENSITIVE, KEEP CO
• Hazardous Substances Data: 55552-70-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
3-Furanboronic acid is used as a coupling partner for various chemical reactions, facilitating the formation of new compounds and contributing to the synthesis of a wide range of products.
Used in Biosensor and Biofuel Cell Fabrication:
3-Furanboronic acid is used as a key component in the fabrication of amperometric biosensors and biofuel cells. Specifically, it is utilized in the preparation of a chitosan uricase (UOx)-poly (furan-3-boronic acid) (PFBA)-Pd nanoparticles (PdNPs)/plated Pd (Pd plate)/multiwalled carbon nanotubes (MWCNTs)/Au electrode, which is essential for the detection and conversion of uric acid in these applications.
Used in Pharmaceutical and Biomedical Applications:
Although not explicitly mentioned in the provided materials, 3-Furanboronic acid's versatility in chemical synthesis and its potential use in the development of novel drug delivery systems and therapeutic agents make it a promising candidate for pharmaceutical and biomedical applications. Its ability to form stable complexes with other molecules can be exploited for targeted drug delivery and the development of new therapeutic strategies.

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

Upstream product

• 22037-28-1 3-bromofurane 
• 5419-55-6 Triisopropyl borate 
• 13675-18-8 tetrahydroxydiboron 

Downstream Products

• 93349-98-5 Methyl 5-(3-Furyl)nicotinate 
• 1027910-63-9 {5-[3-(4-furan-3-yl-phenoxy)-propoxy]-indan-1-yl}-acetic acid ethyl ester 
• 545426-66-2 2-[4-(3-furanyl)phenyl]pyrimidine 
• 208988-20-9 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(3-furanyl)pyrazole 
• 214353-55-6 N-[4-(4-(furan-3-yl)phenoxy)benzenesulfonyl]-S-[(pyrid-2-yl)methyl]-D-penicillamine 
• 622860-55-3 9-hydroxy-4-pyridin-3-yl-6H-pyrrolo[3,4-c]carbazole-1,3-dione 
• 622860-48-4 9-Hydroxy-4-(3-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione 

Relevant articles and documents

Development of a Concise Multikilogram Synthesis of LPA-1 Antagonist BMS-986020 via a Tandem Borylation-Suzuki Procedure

The process development for the synthesis of BMS-986020 (1) via a palladium catalyzed tandem borylation/Suzuki reaction is described. Evaluation of conditions culminated in an efficient borylation procedure using tetrahydroxydiboron followed by a tandem Suzuki reaction employing the same commercially available palladium catalyst for both steps. This methodology addressed shortcomings of early synthetic routes and was ultimately used for the multikilogram scale synthesis of the active pharmaceutical ingredient 1. Further evaluation of the borylation reaction showed useful reactivity with a range of substituted aryl bromides and iodides as coupling partners. These findings represent a practical, efficient, mild, and scalable method for borylation.

Vaulted biaryls in catalysis: A structure-activity relationship guided tour of the immanent domain of the VANOL ligand

The active site in the BOROX catalyst is a chiral polyborate anion (boroxinate) that is assembled in situ from three equivalents of B(OPh) 3 and one of the VANOL ligand by a molecule of substrate. The substrates are bound to the boroxinate by Hbonds to oxygen atoms O1-O3. The effects of introducing substituents at each position of the naphthalene core of the VANOL ligand are systematically investigated in an aziridination reaction. Substituents in the 4,4′- and 8,8′-positions have a negative effect on catalyst performance, whereas, substituents in the 7- and 7′-positions have the biggest impact in a positive direction. VANOL destination: The active site in the BOROX catalyst is a chiral polyborate anion (boroxinate; see figure) that is assembled in situ from three equivalents of B(OPh)3 and one of the VANOL ligand by a molecule of substrate. The effects of introducing substituents at each position of the naphthalene core of the VANOL ligand are systematically investigated in an aziridination reaction. Copyright

Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4]

Arylboronic acids are gaining increased importance as reagents and target structures in a variety of useful applications. Recently, the palladium-catalyzed synthesis of arylboronic acids employing the atom-economical tetrahydroxydiboron (BBA) reagent has been reported. The high cost associated with palladium, combined with several limitations of both palladium- and copper-catalyzed processes, prompted us to develop an alternative method. Thus, the nickel-catalyzed borylation of aryl and heteroaryl halides and pseudohalides using tetrahydroxydiboron (BBA) has been formulated. The reaction proved to be widely functional group tolerant and applicable to a number of heterocyclic systems. To the best of our knowledge, the examples presented here represent the only effective Ni-catalyzed Miyaura borylations conducted at room temperature.

Total synthesis of (+)-cacospongionolide B

Total synthesis of (+)-cacospongionolide B was achieved. The synthesis involved highly stereoselective C-glycosidation of a glycal derived from D-arabinose with 3-furyl boronic acid in the presence of a palladium catalyst and S-alkyl Suzuki-Miyaura coupling of in situ generated alkylborane prepared by the reaction of vinyl trans-decaMn with alkenyl triflate.

Improved replicon cellular activity of non-nucleoside allosteric inhibitors of HCV NS5B polymerase: From benzimidazole to indole scaffolds

Benzimidazole-based allosteric inhibitors of the hepatitis C virus (HCV) NS5B polymerase were diversified to a variety of topologically related scaffolds. Replacement of the polar benzimidazole core by lipophilic indoles led to inhibitors with improved potency in the cell-based subgenomic HCV replicon system. Transposing the indole scaffold into a previously described series of benzimidazole-tryptophan amides generated the most potent inhibitors of HCV RNA replication in cell culture reported to date in this series (EC50 ～ 50 nM).

Synthesis and pharmacological evaluation of 3-(2-furyl)- and 3-(3-furyl)8-chloropyrazolo[5,1-c][1,2,4]benzotriazine 5-oxides, new 3-heteroaryl substituted Benzodiazepine Receptor ligands

The synthesis of 3-(2-furyl)- and 3-(3-furyl)-8-chloropyrazolo[5,1-c][1,2,4]benzotriazine 5-oxides is reported. The binding affinities at the central Benzodiazepine Receptor (BZR) and the muscle relaxant, anticonvulsant and anxiolytic activities of new furyl derivatives are compared to those of the 3-heteroarylderivatives, BZR ligands previously reported by us. The results confirm the stringent spatial requisites of the lipophilic pocket that accommodates the 3-substituent, which seems to influence both the binding and intrinsic activity of this new class of ligands.

Metalloproteinase inhibitors, pharmaceutical compositions containing them, and their use

The present invention is directed to compound of the formula I: STR1 wherein R1, R2, R3, R4, R5, X, Y, and STR2 are as defined herein. These compounds are useful for inhibiting the activity of a metalloproteinase by contacting the metalloproteinase with an effective amount of the inventive compounds.