ChemicalBook > CAS DataBase List > 2,6-Difluoropyridine-3-boronic acid

2,6-Difluoropyridine-3-boronic acid

Product Name
2,6-Difluoropyridine-3-boronic acid
CAS No.
136466-94-9
Chemical Name
2,6-Difluoropyridine-3-boronic acid
Synonyms
uoropyridine-3-boronic acid;3-Borono-2,6-difluoropyridine;2,6-DIFLUOROPYRIDINE-3-BORONIC;2,6-Difluoropyridine-3-boronicaci;2,6-DIFLUORO-3-PYRIDYL BORONIC ACID;2,6-DIFLUOROPYRIDINE-3-BORONIC ACID;(2,6-DIFLUOROPYRIDIN-3-YL)BORONIC ACID;(2,6-DIFLUORO-3-PYRIDINYL)-BORONIC ACID;2,6-difluoropyridin-3-yl-3-boronic acid;6-Chloro-2-fluoropyridine-3-boronic acid
CBNumber
CB0285047
Molecular Formula
C5H4BF2NO2
Formula Weight
158.9
MOL File
136466-94-9.mol
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2,6-Difluoropyridine-3-boronic acid Property

Melting point:
168 °C(Solv: ethyl acetate (141-78-6); ethyl ether (60-29-7))
Boiling point:
314.8±52.0 °C(Predicted)
Density 
1.44±0.1 g/cm3(Predicted)
storage temp. 
Inert atmosphere,2-8°C
Water Solubility 
Soluble in water
form 
powder to crystal
pka
6.77±0.58(Predicted)
color 
White to Light yellow
InChIKey
LCCZTROJRJFXNV-UHFFFAOYSA-N
CAS DataBase Reference
136466-94-9(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-37
HS Code 
29333990
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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.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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.

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N-Bromosuccinimide Price

TCI Chemical
Product number
D4006
Product name
2,6-Difluoro-3-pyridineboronic Acid (contains varying amounts of Anhydride)
Packaging
1g
Price
$33
Updated
2025/07/31
TCI Chemical
Product number
D4006
Product name
2,6-Difluoro-3-pyridineboronic Acid (contains varying amounts of Anhydride)
Packaging
5g
Price
$104
Updated
2025/07/31
TRC
Product number
D447488
Product name
2,6-Difluoropyridine-3-boronicacid
Packaging
250mg
Price
$55
Updated
2021/12/16
TRC
Product number
D447488
Product name
2,6-Difluoropyridine-3-boronicacid
Packaging
500mg
Price
$65
Updated
2021/12/16
Usbiological
Product number
270348
Product name
6-Chloro-2-fluoropyridine-3-boronic acid
Packaging
250mg
Price
$368
Updated
2021/12/16
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2,6-Difluoropyridine-3-boronic acid Chemical Properties,Usage,Production

Chemical Properties

2,6-difluoropyridine-3-boronic acid is a fluorine-containing substituted pyridine boronic acid derivatives, due to the fluorine atom and the atomic radius of the hydrogen atom is quite close, so when the hydrogen atom in the molecule is replaced by the fluorine atom, it will not cause the molecule to change the stereo configuration of the significant changes. However, due to the fluorine atom has a strong ability to absorb electrons, often make the original molecule of the electronic properties of the great changes, so that the fluorine-containing pyridine boronic acid has a good stability and a large dielectric anisotropy, so in recent years, the fluorine-containing pyridine boronic acid in medicine, especially the synthesis of new anticancer drugs and the material science has a very important role.

Uses

2,6-Difluoropyridine-3-boronic acid is a pyridine analogue containing a fluorine atom reactive group and boronic acid in its structure. It can be used as a reagent for fluorination or substitution reactions and as a synthetic intermediate for the preparation of other organic compounds.

Synthesis

1513-65-1

121-43-7

136466-94-9

The general procedure for the synthesis of 2,6-difluoropyridine-3-boronic acid from 2,6-difluoropyridine and trimethyl borate was carried out as follows: the synthesis was carried out according to the methodology reported in the literature [S1, S2] with appropriate modifications. First, a solution of lithium diisopropylammonium (LDA) was prepared by slow dropwise addition of a THF (20 mL) solution of diisopropylamine (3.4 mL) to n-butyllithium (1.67 M in n-hexane, 24 mmol, 14 mL) at 20 °C, followed by stirring at 0 °C for 20 min. Next, in another reaction flask, a solution of 2,6-difluoropyridine (20 mmol, 1.8 mL) in THF (20 mL) was stirred at -78 °C and the LDA solution prepared above was added via cannula. After continued stirring at -78 °C for 30 min, a solution of trimethyl borate (24 mmol, 2.5 g, 2.7 mL) in THF (10 mL) was added to the reaction mixture, followed by a slow warming up to room temperature over a period of 1 hour. Upon completion of the reaction, the reaction was quenched with 2 M aqueous sodium hydroxide solution (40 mL). The aqueous layer was separated and the pH was adjusted to 8 with 4 M hydrochloric acid followed by extraction with ethyl acetate (organic layer A). The pH of the aqueous layer was further adjusted to 6.5 with 4M hydrochloric acid, at which time insoluble organic matter was precipitated, and the extraction was repeated three times with ethyl acetate to give organic layer B. The pH of the aqueous layer was again adjusted to 4 with 4M hydrochloric acid, and the extraction was repeated three times with ethyl acetate to give organic layer C. Organic layers B and C were combined, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to afford the crude product of 2,6-difluoropyridinium-3-boronate in 94% (3.0 g) yield. 94% (3.0 g, 19 mmol). The product could be used directly in the subsequent reaction without further purification.

References

[1] Journal of Fluorine Chemistry, 2016, vol. 181, p. 56 - 60
[2] Inorganic Chemistry, 2009, vol. 48, # 3, p. 1030 - 1037
[3] Patent: EP2727928, 2014, A1. Location in patent: Paragraph 0027
[4] Patent: US8859771, 2014, B2. Location in patent: Page/Page column 11
[5] Journal of Nanoscience and Nanotechnology, 2018, vol. 18, # 10, p. 7047 - 7052

2,6-Difluoropyridine-3-boronic acid Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 2,6-Difluoropyridine-3-boronic acid manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
2,6-Difluoropyridine-3-boronic acid 136466-94-9
Price
US $1.10/g
Min. Order
1g
Purity
99.0% min
Supply Ability
100 tons min
Release date
2021-05-25
Zhuozhou Wenxi import and Export Co., Ltd
Product
2,6-Difluoropyridine-3-boronic acid 136466-94-9
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-08-11
Zhuozhou Wenxi import and Export Co., Ltd
Product
2,6-Difluoro-3-pyridineboronic Acid (contains varying amounts of Anhydride) 136466-94-9
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-06-27

136466-94-9, 2,6-Difluoropyridine-3-boronic acidRelated Search:

2,6-Difluorobenzamide 2,6-Dimethylphenol 2,6-Diphenylphenol Pyridine-2,6-dicarboxylic acid 2,6-Diaminoanthraquinone 2,6-Diaminopyridine 3-Pyridylboronic acid 2,6-Difluoropyridine 2,6-DIFLUOROPYRIDINE-4-BORONIC ACID 2,6-DIFLUOROPYRIDINE-3-BORONIC ACID HYDRATE 2,6-Difluoropyridine-3-boronic acid 2,6-DIFLUORO-3-(4,4,5,5-TETRAMETHYL-[1,3,2]-DIOXABOROLAN-2-YL)PYRIDINE 2,3-DIFLUOROPYRIDINE-5-BORONIC ACID PINACOL ESTER 3,5-DIFLUOROPYRIDINE-4-BORONIC ACID HYDRATE 3,5-DIFLUOROPYRIDINE-4-BORONIC ACID PINACOL ESTER 3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)-2,6-difluoropyridine 2,6-DIFLUOROPYRIDINE-3-BORONIC ACID, PINACOL ESTER 2,6-Difluoro-3-(4,4,6-trimethyl-1,3,2-dioxaborinan-2-yl)pyridine

  • Boronic acid, (2,6-difluoro-3-pyridinyl)- (9CI)
  • (2,6-DIFLUORO-3-PYRIDINYL)-BORONIC ACID
  • 2,6-DIFLUORO-3-PYRIDYL BORONIC ACID
  • (2,6-DIFLUOROPYRIDIN-3-YL)BORONIC ACID
  • 2,6-DIFLUOROPYRIDINE-3-BORONIC ACID
  • 6-Chloro-2-fluoropyridine-3-boronic acid
  • REF DUPL: 2,6-Difluoropyridine-3-boronic acid
  • 2,6-Difluoro-3-pyridineboronic Acid (contains varying amounts of Anhydride)
  • 3-Borono-2,6-difluoropyridine
  • 2,6-difluoropyridin-3-yl-3-ylboronic acid
  • 2,6-Difluoro-3-pyridineboronic Acid (contains of Anhydride)
  • 2,6-DIFLUOROPYRIDINE-3-BORONIC
  • 2,6-difluoropyridin-3-yl-3-boronic acid
  • uoropyridine-3-boronic acid
  • Boronic acid, B-(2,6-difluoro-3-pyridinyl)-
  • 2,6-Difluoropyridine-3-boronicaci
  • 2,6-Difluoropyridine-3-boronic acid ISO 9001：2015 REACH
  • B-(2,6-Difluoro-3-pyridinyl)boronic acid
  • 2,6-Difluoropyridine-3-boronic acid（contains varying amounts of Anhydride)
  • 2,6-Difluoropyridine-3-boronic acid - [D3535]
  • B-(2,6-Difluoropyridin-3-yl)boronic acid
  • 136466-94-9
  • C5H4BF2NO3
  • Boronic Acid
  • Boronic Acids & Esters
  • Boronic Acids & Esters
  • Pyridines
  • HALIDE