4-Pyridinylboronic acid
Product Information
Molecular Formula
C5H6BNO2
Molecular Weight
122.92
Description
4-Pyridinylboronic acid is a versatile organoboron compound widely utilized in organic synthesis and pharmaceutical research. Known for its ability to form stable covalent bonds with diols, it is frequently employed in Suzuki-Miyaura cross-coupling reactions, facilitating the construction of complex molecular architectures. Its unique pyridine ring structure enhances its reactivity and selectivity in various chemical transformations. As a key reagent, 4-Pyridinylboronic acid plays a crucial role in advancing the development of new chemical entities and materials.
Synonyms
Pyridine-4-boronic acid; 4-Pyridylboronic Acid; (pyridin-4-yl)boronic acid; B-4-Pyridinylboronic Acid; 4-Pyridineboronic acid; Boronic acid, 4-pyridinyl-; AC-14907; AK-26762; BC000193; BP-10299
IUPAC Name
pyridin-4-ylboronic acid
SMILES
B(C1=CC=NC=C1)(O)O
InChI
InChI=1S/C5H6BNO2/c8-6(9)5-1-3-7-4-2-5/h1-4,8-9H
InChI Key
QLULGIRFKAWHOJ-UHFFFAOYSA-N
Boiling Point
308.8±34.0 °C (Predicted)
Melting Point
> 300 °C
Purity
> 98 % (HPLC)
Density
1.220±0.10 g/cm3 (Predicted)
Solubility
Slightly soluble in Aqueous Acid, Water
Appearance
Pale orange granular powder
Storage
2-8 °C under inert atmosphere
LogP
-1.23860
Safety Information
Precautionary Statement
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501
Signal Word
Warning
Computed Properties
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Exact Mass
123.0491586 g/mol
Monoisotopic Mass
123.0491586 g/mol
Topological Polar Surface Area
53.4Ų
Heavy Atom Count
9
Formal Charge
0
Complexity
83
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| CN-113980008-A | Light extraction material, light-emitting device, display panel and display device | 2021-10-29 |
| CN-113999266-A | Binuclear metal platinum complex and organic electroluminescent device | 2021-10-28 |
| CN-113912858-A | Porous polymer for detecting nitro compound and preparation method thereof | 2021-10-27 |
| CN-114069044-A | Anode material and lithium ion battery containing same | 2021-10-27 |
| CN-113788861-A | Metal iridium (III) complex and preparation method and application thereof | 2021-10-14 |
| CN-113845534-A | Preparation method and application of luminescent crystal material for detecting high manganese acid radical in extremely sensitive water phase | 2021-09-24 |
| CN-113773246-A | Preparation method of 2-substituted-4-trifluoromethylpyridine | 2021-09-16 |
| CN-113845515-A | Aromatic heterocyclic structure-containing dimethyl biphenyl diaryl pyrimidine derivative and preparation method and application thereof | 2021-09-03 |
| CN-113735762-A | Water-soluble fluorescent probe with aggregation-induced emission characteristic and preparation method and application thereof | 2021-08-31 |
| CN-113620940-A | Preparation of near-infrared absorbing amphiphilic diarylethene photochromic molecules and application of reversible photo-thermal and photo-acoustic molecules | 2021-08-18 |
Literatures
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| 21936546 | 2011-11-04 | Synthesis of functionalized cinnamaldehyde derivatives by an oxidative Heck reaction and their use as starting materials for preparation of Mycobacterium tuberculosis 1-deoxy-D-xylulose-5-phosphate reductoisomerase inhibitors | The Journal of organic chemistry |
| 21754261 | 2011-05-01 | trans-Dichloridobis[(pyridin-4-yl)boronic acid-κN]palladium(II) dimethyl sulfoxide disolvate | Acta crystallographica. Section E, Structure reports online |
| 21088793 | 2011-01-14 | Synthesis, carbohydrate- and DNA-binding studies of cationic 2,2':6',2''-terpyridineplatinum(II) complexes containing N- and S-donor boronic acid ligands | Dalton transactions (Cambridge, England : 2003) |
| 20667740 | 2010-09-15 | Novel tricyclic pyrazole BRAF inhibitors with imidazole or furan central scaffolds | Bioorganic & medicinal chemistry |
| 21378917 | 2009-09-01 | Metal-free carbon-carbon bond-forming reductive coupling between boronic acids and tosylhydrazones | Nature chemistry |
| 17933583 | 2008-08-01 | An experimental and theoretical study of molecular structure and vibrational spectra of 3- and 4-pyridineboronic acid molecules by density functional theory calculations | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy |
| 17784957 | 2007-09-04 | A novel p38 alpha MAPK inhibitor suppresses brain proinflammatory cytokine up-regulation and attenuates synaptic dysfunction and behavioral deficits in an Alzheimer's disease mouse model | Journal of neuroinflammation |
