5-Fluoropyridin-3-ylboronic acid
- Product Name
- 5-Fluoropyridin-3-ylboronic acid
- CAS No.
- 872041-86-6
- Chemical Name
- 5-Fluoropyridin-3-ylboronic acid
- Synonyms
- CAS:872041-86-6;Boric acid fluoride-3-5;3-Borono-5-fluoropyridine;5-fluoro-3-pyridylboronic acid;Fluoro-3-pyridine boronic acid;3-FLUOROPYRIDINE-5-BORONIC ACID;5-FLUORO-3-PYRIDINEBORONIC ACID;5-FLUOROPYRIDINE-3-BORONIC ACID;3-Fluoropyridin-5-ylboronic acid;3-fluoro-5-pyridine boronic acid
- CBNumber
- CB9752878
- Molecular Formula
- C5H5BFNO2
- Formula Weight
- 140.91
- MOL File
- 872041-86-6.mol
5-Fluoropyridin-3-ylboronic acid Property
- Melting point:
- 233-236
- Boiling point:
- 292.9±50.0 °C(Predicted)
- Density
- 1.34±0.1 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- Soluble in hot methanol.
- form
- Crystalline Powder
- pka
- 5.85±0.10(Predicted)
- color
- White to off-white
- InChI
- InChI=1S/C5H5BFNO2/c7-5-1-4(6(9)10)2-8-3-5/h1-3,9-10H
- InChIKey
- FVEDGBRHTGXPOK-UHFFFAOYSA-N
- SMILES
- B(C1=CC(F)=CN=C1)(O)O
Safety
- Hazard Codes
- Xi
- Risk Statements
- 37/38-41-36/37/38
- Safety Statements
- 26-39-37
- Hazard Note
- Irritant/Keep Cold
- HS Code
- 29319090
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
- F0859
- Product name
- 5-Fluoropyridine-3-boronic Acid (contains varying amounts of Anhydride)
- Packaging
- 1g
- Price
- $103
- Updated
- 2025/07/31
- Product number
- F0859
- Product name
- 5-Fluoropyridine-3-boronic Acid (contains varying amounts of Anhydride)
- Packaging
- 5g
- Price
- $359
- Updated
- 2025/07/31
- Product number
- F596195
- Product name
- 5-Fluoropyridine-3-boronicacid
- Packaging
- 1g
- Price
- $105
- Updated
- 2021/12/16
- Product number
- F596195
- Product name
- 5-Fluoropyridine-3-boronicacid
- Packaging
- 100mg
- Price
- $45
- Updated
- 2021/12/16
- Product number
- CS-D0337
- Product name
- 5-FLUOROPYRIDIN-3-YLBORONICACID
- Purity
- 98.77%
- Packaging
- 5g
- Price
- $64
- Updated
- 2021/12/16
5-Fluoropyridin-3-ylboronic acid Chemical Properties,Usage,Production
Chemical Properties
5-Fluoro-3-pyridineboronic acid is an important raw material for Suzuki cross-coupling reaction, which can be used for conjugate addition reaction with carboxylic compounds containing a, β unsaturated bond. In many pharmaceuticals, pesticides, ionic liquids and other molecules contain pyridine structure, using 5-fluoro-3-pyridineboronic acid as raw material, through Suzuki coupling reaction; the pyridine ring can be introduced into the molecule, and the reaction conditions are mild, the yield is high and environmentally friendly.
Uses
suzuki reaction
Uses
5-Fluoropyridine-3-boronic acid is used as pharmaceutical intermediate.
Synthesis
407-20-5
872041-86-6
General procedure for the synthesis of 5-fluoro-3-pyridineboronic acid from 3-bromo-5-fluoropyridine: 3-bromo-5-fluoropyridine (25 Kg, 142 moles, 1.0 eq.), THF (222.5 Kg), and isopropyl borate (28 Kg, 149.3 moles, 1.05 eq.) were added to a 700 L cryogenic reactor. The resulting mixture was cooled to -90°C to -80°C with continuous stirring. Subsequently, n-butyllithium (40.2 Kg, 2.5 M, 142 moles, 1.0 eq.) was added dropwise at a rate of 2 Kg/h and it was ensured that the reaction temperature was maintained below -87 °C. After the dropwise addition was completed, the reaction mixture was kept at -88 °C to -83 °C for 2.5 hours. After confirming the completion of the reaction by HPLC analysis, a 9% aqueous hydrochloric acid solution (7.7 Kg) was added to quench the reaction. The mixture was transferred to a 1000 L glass-lined reactor to bring the temperature back to -20°C to -10°C. Next, additional hydrochloric acid solution (122.3 Kg) was added until the pH was adjusted to 1-2, during which time the temperature was maintained at 0-10°C. The mixture was kept under these conditions for 0.5 hours to promote phase separation. After separation of the organic layer, it was washed with saturated brine (38 Kg), stirred for 0.5 h and left for another 0.5 h to achieve phase separation. The aqueous layer was separated and the combined aqueous layers were extracted twice with ethyl acetate (51Kg and 25Kg). After separation of the organic phase, the pH was adjusted to 6 with 30% aqueous sodium hydroxide (27.4 Kg). at this pH, the solid product precipitated. The slurry was filtered by centrifugation and dried in a disk drier at 40-45°C to give 5-fluoro-3-pyridineboronic acid as a white solid (17.5 Kg, yield 87.4%, purity: 98.6% AUC, determined using Method B).
References
[1] Patent: WO2009/61875, 2009, A2. Location in patent: Page/Page column 36-37
5-Fluoropyridin-3-ylboronic acid Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 5-Fluoropyridin-3-ylboronic acid manufacturers
- Product
- 5-Fluoropyridin-3-ylboronic acid 872041-86-6
- Price
- US $1.00/KG
- Min. Order
- 1G
- Purity
- 98%
- Supply Ability
- 1000KG
- Release date
- 2018-08-10