3-Pyridylboronic acid
- Product Name
- 3-Pyridylboronic acid
- CAS No.
- 1692-25-7
- Chemical Name
- 3-Pyridylboronic acid
- Synonyms
- PYRIDIN-3-YLBORONIC ACID;3-PYRIDINEBORONIC ACID;PYRIDINE-3-BORONIC ACID;3-PyridyL;3-PYRIDINYLBORONIC ACID;DFD3;AKOS BRN-0272;Pyridine-3-acid;3-Boronopyridine;RARECHEM AH PB 0251
- CBNumber
- CB9111390
- Molecular Formula
- C5H6BNO2
- Formula Weight
- 122.92
- MOL File
- 1692-25-7.mol
3-Pyridylboronic acid Property
- Melting point:
- >300 °C (lit.)
- Boiling point:
- 308.8±34.0 °C(Predicted)
- Density
- 1.22±0.1 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- Slightly soluble in methanol.
- form
- Powder, Crystals and/or Chunks
- pka
- 4.00±0.10(Predicted)
- color
- White to yellow-orange
- BRN
- 471943
- InChI
- InChI=1S/C5H6BNO2/c8-6(9)5-2-1-3-7-4-5/h1-4,8-9H
- InChIKey
- ABMYEXAYWZJVOV-UHFFFAOYSA-N
- SMILES
- C1=NC=CC=C1B(O)O
- CAS DataBase Reference
- 1692-25-7(CAS DataBase Reference)
Safety
- Hazard Codes
- Xn,Xi,C,F
- Risk Statements
- 36/37/38-22-34-11
- Safety Statements
- 36/37/39-3-26-45-16
- WGK Germany
- 3
- Hazard Note
- Irritant
- HazardClass
- IRRITANT, KEEP COLD
- HS Code
- 29349990
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405Store locked up.
N-Bromosuccinimide Price
- Product number
- 512125
- Product name
- 3-Pyridinylboronic acid
- Purity
- ≥95.0%
- Packaging
- 1g
- Price
- $90.06
- Updated
- 2025/07/31
- Product number
- 512125
- Product name
- 3-Pyridinylboronic acid
- Purity
- ≥95.0%
- Packaging
- 5g
- Price
- $259.02
- Updated
- 2025/07/31
- Product number
- P1673
- Product name
- 3-Pyridylboronic Acid (contains varying amounts of Anhydride)
- Packaging
- 1g
- Price
- $20
- Updated
- 2025/07/31
- Product number
- P1673
- Product name
- 3-Pyridylboronic Acid (contains varying amounts of Anhydride)
- Packaging
- 5g
- Price
- $51
- Updated
- 2025/07/31
- Product number
- 512125
- Product name
- 3-Pyridinylboronic acid
- Purity
- ≥95.0%
- Packaging
- 25g
- Price
- $268
- Updated
- 2025/07/31
3-Pyridylboronic acid Chemical Properties,Usage,Production
Chemical Properties
Light Yellow Powder
Uses
Boronic acid derivatives and their binding affinities with diols.
Uses
suzuki reaction
Uses
3-Pyridylboronic acid is a reagent used for• ;Phosphine-free Suzuki-Miyaura cross-coupling reactions
1 ;Regioselective Suzuki-Miyaura coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulation
2 ;N-arylation using copper acetylacetonate catalyst
3 ;Copper-mediated cyanation and regioselective cyanation of electron-rich benzenes
4 Reagent use in Preparation of • ;New linear poly(phenylpyridyl) chains by Suzuki coupling
5 ;Oligopyridyl foldamers as mimics of a-helix twist
6 ;Many highly significant therapeutic enzymatic and kinase inhibitors and r
Synthesis Reference(s)
The Journal of Organic Chemistry, 64, p. 3846, 1999 DOI: 10.1021/jo9819279
Tetrahedron Letters, 43, p. 4285, 2002
Synthesis
626-55-1
5419-55-6
1692-25-7
The general procedure for the synthesis of pyridine-3-boronic acid from 3-bromopyridine and triisopropyl borate was as follows: first, pyridine-3-boronic acid (1-6) was prepared by subsequent hydrolysis via an appropriate esterification reaction according to the method of Cai et al. (Tetrahedron Lett. 43: 4285-4287, 2002). This was done as follows: 85 mL of toluene was added to a 500 mL three-necked flask, cooled to below -60°C, and then 1.6 M of n-BuLi hexane solution (48.6 mL, 77.8 mmol) was added dropwise over 10 min. After the internal temperature reached -60°C, a toluene solution (30 mL) of 3-bromopyridine (6.8 mL, 70.7 mmol) was slowly added dropwise to keep the internal temperature below -50°C. At this point, a brownish-black solid precipitated, and the resulting slurry was stirred for 20 min. Next, 30 mL of THF was added dropwise to keep the internal temperature below -50°C and stirring was continued for 15 min. Subsequently, triisopropyl borate (19.6 mL, 84.9 mmol) was added all at once via syringe. The solution was slowly heated to -15°C, and the reaction was quenched with 2.7 N aqueous HCl (70.0 mL) and transferred to a partition funnel. The aqueous layer was separated and the organic layer was washed with 10 mL of water. The combined aqueous layers were neutralized to pH 7 with 10 N NaOH aqueous solution and extracted with THF (200 mL x 1, 125 mL x 2). The organic phases were combined and concentrated under reduced pressure. The residue was dissolved in THF/CH3OH (1:1, 140 mL), filtered and diluted with CH3CN to 300 mL.The solvent was converted to CH3CN by distillation and concentrated to 100 mL.The solids were collected by filtration to afford pyridine-3-boronic acid 1 (6.4 g, 73% yield) as an off-white solid. The product was confirmed by 1H NMR (CD3OD): δ 8.64 (br s, 1H), 8.50 (m, 1H), 8.38 (br s, 1H), 7.65 (br s, 1H). The product can be used directly in Suzuki cross-coupling reaction.
References
[1] Patent: WO2005/66162, 2005, A1. Location in patent: Page/Page column 92
[2] Organic Syntheses, 2005, vol. 81, p. 89 - 97
3-Pyridylboronic acid Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 3-Pyridylboronic acid manufacturers
- Product
- 3-Pyridylboronic acid 1692-25-7
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 98%min
- Supply Ability
- 30tons/month
- Release date
- 2023-01-31
- Product
- 3-Pyridylboronic acid 1692-25-7
- Price
- US $10.00/KG
- Min. Order
- 100KG
- Purity
- 99%
- Supply Ability
- 100 mt
- Release date
- 2024-12-03
- Product
- 3-Pyridylboronic acid 1692-25-7
- Price
- US $10.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20 ton
- Release date
- 2024-12-06