Boninic acid
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| Category | Others |
| Catalog number | BBF-05449 |
| CAS | 548-85-6 |
| Molecular Weight | 460.52 |
| Molecular Formula | C25H32O8 |
| Purity | ≥98% by HPLC |
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Specification
| Synonyms | 3-(2,4-Dimethoxy-6-propylbenzoyloxy)-4-methoxy-6-pentylsalicylic acid; Benzoic acid, 3-[(2,4-dimethoxy-6-propylbenzoyl)oxy]-2-hydroxy-4-methoxy-6-pentyl-; 6-Hydroxy-4-methoxy-5-(4,6-dimethoxy-2-propyl-benzoyloxy)-2-pentyl-benzoesaeure; Boninsaeure |
| Storage | Store at 2-8°C |
| IUPAC Name | 3-(2,4-dimethoxy-6-propylbenzoyl)oxy-2-hydroxy-4-methoxy-6-pentylbenzoic acid |
| Canonical SMILES | CCCCCC1=CC(=C(C(=C1C(=O)O)O)OC(=O)C2=C(C=C(C=C2OC)OC)CCC)OC |
| InChI | InChI=1S/C25H32O8/c1-6-8-9-11-16-13-19(32-5)23(22(26)21(16)24(27)28)33-25(29)20-15(10-7-2)12-17(30-3)14-18(20)31-4/h12-14,26H,6-11H2,1-5H3,(H,27,28) |
| InChI Key | GOWJVQGHIKADDP-UHFFFAOYSA-N |
Properties
| Appearance | Crystal |
| Boiling Point | 641.1±55.0°C at 760 mmHg |
| Melting Point | 133°C |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. Emergent Organoboron Acid Catalysts
Brian J Graham, Ronald T Raines J Org Chem. 2022 Nov 14. doi: 10.1021/acs.joc.2c01695. Online ahead of print.
Organoboron acids are stable, organic-soluble Lewis acids with potential application as catalysts for a wide variety of chemical reactions. In this review, we summarize the utility of boronic and borinic acids, as well as boric acid, as catalysts for organic transformations. Typically, the catalytic processes exploit the Lewis acidity of trivalent boron, enabling the reversible formation of a covalent bond with oxygen. Our focus is on recent developments in the catalysis of dehydration, carbonyl condensation, acylation, alkylation, and cycloaddition reactions. We conclude that organoboron acids have a highly favorable prospectus as the source of new catalysts.
2. Electron-Deficient Borinic Acid Polymers: Synthesis, Supramolecular Assembly, and Examination as Catalysts in Amide Bond Formation
Monika K Baraniak, Roger A Lalancette, Frieder Jäkle Chemistry. 2019 Oct 28;25(60):13799-13810. doi: 10.1002/chem.201903196. Epub 2019 Sep 30.
The Lewis acidic character of borinic-acid-functionalized polymers suggests broad potential applications in supramolecular materials, chemo- and biosensors, as well as supported catalysts. Two highly electron-deficient borinic acid copolymers (3 a and 3 b) with variable steric hindrance at the boron center were prepared by reaction of aryldibromoboranes ArBBr2 (2, Ar=2,4-Cl2 Ph, 3,5-Cl2 Ph) with a 10 % stannylated polystyrene random copolymer, followed by conversion to the desired PS-B(Ar)OH functionalities. The supramolecular assembly of these polymers through Lewis acid-Lewis base interactions and reversible covalent B-O-B bond formation was investigated. Exposure of a polymer solution of 3 a to pyridine triggered spontaneous gelation, whereas 3 b only gelled upon addition of molecular sieves to favor formation of boroxane crosslinks. The crosslinking process was readily reversed by addition of small amounts of water or wet solvent. The dynamic processes were studied in detail by variable-temperature (VT) NMR by using molecular model compounds. The polymers and their corresponding model compounds were also examined as catalysts in the amide bond formation reaction between phenylacetic acid and benzylamine. The 3,5-dichlorophenyl borinic acid derivatives proved to be the more effective catalysts. Mechanistic studies suggested that the borane Lewis acid-catalyzed coupling involves initial acid-induced protodeboronation to release the dichlorophenyl boronic acid as the active catalyst.
3. Borinic Acid Catalyzed Regioselective N-Alkylation of Azoles
Shrey P Desai, Matthew T Zambri, Mark S Taylor J Org Chem. 2022 Apr 15;87(8):5385-5394. doi: 10.1021/acs.joc.2c00281. Epub 2022 Apr 6.
A method for regioselective N-alkylation of ambident, azole-type heterocycles with alkene or epoxide electrophiles is described. In the presence of diphenylborinic acid (Ph2BOH) and an amine cocatalyst, heterocyclic nucleophiles such as 1,2,3- and 1,2,4-triazoles, substituted tetrazoles, and purine are activated toward selective N-functionalization. The scope of electrophilic partners includes enones, 2-vinylpyridine, phenyl vinyl sulfone, a dehydroalanine derivative, and epoxides. Mechanistic studies, including in situ 11B NMR spectroscopy and kinetic analysis, are discussed.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
