2-Bromo-5-fluoropyridine

Bezeichnung:2-Bromo-5-fluoropyridine

CAS-Nr41404-58-4

Englisch Name:2-Bromo-5-fluoropyridine

CBNumberCB9683345

SummenformelC5H3BrFN

Molgewicht175.99

MOL-Datei41404-58-4.mol

2-Bromo-5-fluoropyridine physikalisch-chemischer Eigenschaften

Schmelzpunkt	30-31 °C (lit.)
Siedepunkt	80-83 °C/44 mmHg (lit.)
Dichte	1.707±0.06 g/cm3(Predicted)
Brechungsindex	1.5396
Flammpunkt	167 °F
storage temp.	Inert atmosphere,Room Temperature
pka	-1.63±0.10(Predicted)
Aggregatzustand	Liquid
Farbe	Colorless to slightly yellow
BRN	1561456
InChI	InChI=1S/C5H3BrFN/c6-5-2-1-4(7)3-8-5/h1-3H
InChIKey	UODINHBLNPPDPD-UHFFFAOYSA-N
SMILES	C1(Br)=NC=C(F)C=C1
CAS Datenbank	41404-58-4(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn,F
R-Sätze:	36/37/38-20/21/22-10
S-Sätze:	26-36-16
RIDADR	2811
WGK Germany	3
Hazard Note	Irritant
HazardClass	6.1
PackingGroup	III
HS Code	29333990
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

2-Bromo-5-fluoropyridine Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R10:Entzündlich.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S16:Von Zündquellen fernhalten - Nicht rauchen.
Chemische Eigenschaften
Light yellow Cryst
Verwenden
2-Bromo-5-fluoropyridine can be used in the synthesis of the following:
- 5-fluoro-2-phenylpyridine via Suzuki coupling reaction with phenylboronic acid
- 5-fluoro-2-(p-tolyl)pyridine via Suzuki coupling reaction with p-tolylboronic acid
It can undergo palladium-catalyzed homo-coupling reaction to give the corresponding biaryl. It can also be employed in a palladium-catayzed α-arylation of esters leading to 4-pyridylcarboxypiperidines.
Verwenden
2-Bromo-5-fluoropyridine is used in the synthesis of mGluR5 antagonist for the treatment of neuropathic pain.
Synthese

21717-96-4

41404-58-4

Example C Synthesis of 2-bromo-5-fluoropyridine: 2-Amino-5-fluoropyridine (6.5 g, 58 mmol) was added in batches to 48% hydrobromic acid (28.8 mL, 296 mmol) cooled to 0-5 °C. A solution formed from bromine (8.9 mL, 174 mmol) and sodium nitrite (10 g, 145 mmol) dissolved in 20 mL of water was added slowly and dropwise at 0-5 °C (note: nitrogen release). The reaction mixture was stirred for 1 hour and then quenched with concentrated hydrochloric acid. A 32% sodium hydroxide solution (50.5 mL, 0.55 mol) was then added. The reaction mixture was continued to be stirred for 20 minutes at room temperature and then extracted three times with ether. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure at 30 °C and 500 mbar (note: the product is volatile). The crude product was purified by rapid chromatography on silica gel with an elution gradient of dichloromethane/pentane (0:100 → 50:50). The final product was 2-bromo-5-fluoropyridine (6.7 g, 66% yield) in light yellow solid form.
Einzelnachweise
[1] Patent: US2007/78155, 2007, A1. Location in patent: Page/Page column 29
[2] Patent: WO2016/44323, 2016, A1. Location in patent: Paragraph 0268
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 19, p. 5349 - 5352

2-Bromo-5-fluoropyridine Upstream-Materialien And Downstream Produkte

2-Bromo-5-fluoropyridine Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

41404-58-4, 2-Bromo-5-fluoropyridine Verwandte Suche:

Send Inquriy