2-Fluoropyridine-4-boronic acid

Bezeichnung:2-Fluoropyridine-4-boronic acid

CAS-Nr401815-98-3

Englisch Name:2-Fluoropyridine-4-boronic acid

CBNumberCB0438900

SummenformelC5H5BFNO2

Molgewicht140.91

MOL-Datei401815-98-3.mol

2-Fluoropyridine-4-boronic acid physikalisch-chemischer Eigenschaften

Schmelzpunkt	ca 195℃
Siedepunkt	326.8±52.0 °C(Predicted)
Dichte	1.34±0.1 g/cm3(Predicted)
storage temp.	Inert atmosphere,Store in freezer, under -20°C
Löslichkeit	soluble in Methanol
Aggregatzustand	powder to crystal
pka	6.51±0.10(Predicted)
Farbe	White to Almost white
InChI	1S/C5H5BFNO2/c7-5-3-4(6(9)10)1-2-8-5/h1-3,9-10H
InChIKey	WXGBZJJAGLSBPR-UHFFFAOYSA-N
SMILES	OB(O)c1ccnc(F)c1
CAS Datenbank	401815-98-3(CAS DataBase Reference)

Sicherheit

R-Sätze:	36/37/38
S-Sätze:	26-37
WGK Germany	WGK 3
Hazard Note	Irritant
HS Code	29339900
Speicherklasse	11 - Combustible Solids

Gefahreninformationscode (GHS)

2-Fluoropyridine-4-boronic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
Solid
Verwenden
2-Fluoropyridine-4-boronic Acid is used to synthesize analogues of the antitubercular drug.
Synthese

5419-55-6

128071-98-7

401815-98-3

Step 1: 4-bromo-2-fluoropyridine (30.0 g, 0.17 mol) and triisopropyl borate (38.4 g, 0.20 mol) were dissolved in a solvent mixture of anhydrous toluene and tetrahydrofuran (THF) (4:1, 250 mL) under nitrogen protection. The reaction mixture was cooled to -78 °C, followed by slow dropwise addition of n-butyllithium (80 mL, 0.20 mol, 2.5 M hexane solution) over 30 min. After the dropwise addition was completed, stirring was continued at -78 °C for 30 min. The reaction mixture was then slowly warmed up to -20°C over 1 hr. The progress of the reaction was monitored by thin layer chromatography (TLC) (unfolding agent: petroleum ether (PE):ethyl acetate (EtOAc) = 1:1) to confirm that the raw materials were completely consumed. Upon completion of the reaction, the mixture was acidified to pH 2 with 3N HCl (50 mL) and stirred at room temperature for 15 minutes. The reaction mixture was transferred to a partition funnel and extracted with EtOAc (150 mL) and water (150 mL). The organic layer was separated, washed sequentially with water and brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give (2-fluoropyridin-4-yl)boronic acid (22.0 g, 91% yield) as a white solid.
Einzelnachweise
[1] Patent: WO2015/103137, 2015, A1. Location in patent: Paragraph 00178
[2] Patent: US7087755, 2006, B1. Location in patent: Page/Page column 6
[3] Patent: US2004/122237, 2004, A1. Location in patent: Page 201

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