5-Bromo-2-fluoropyridine

Bezeichnung:5-Bromo-2-fluoropyridine

CAS-Nr766-11-0

Englisch Name:5-Bromo-2-fluoropyridine

CBNumberCB0344067

SummenformelC5H3BrFN

Molgewicht175.99

MOL-Datei766-11-0.mol

5-Bromo-2-fluoropyridine physikalisch-chemischer Eigenschaften

Siedepunkt	162-164 °C750 mm Hg(lit.)
Dichte	1.71 g/mL at 25 °C(lit.)
Brechungsindex	n20/D 1.5325(lit.)
Flammpunkt	165 °F
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	DMSO (Slightly), Methanol (Slightly)
pka	-2.79±0.10(Predicted)
Aggregatzustand	Liquid
Farbe	Clear colorless yellow
Wichte	1.710
BRN	1363171
InChI	InChI=1S/C5H3BrFN/c6-4-1-2-5(7)8-3-4/h1-3H
InChIKey	MYUQKYGWKHTRPG-UHFFFAOYSA-N
SMILES	C1(F)=NC=C(Br)C=C1
CAS Datenbank	766-11-0(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	36/37/38-22
S-Sätze:	26-36/37-37/39
RIDADR	UN2810
WGK Germany	3
Hazard Note	Irritant
HazardClass	6.1
PackingGroup	III
HS Code	29339900
Speicherklasse	10 - Combustible liquids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

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

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R22:Gesundheitsschädlich beim Verschlucken.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Beschreibung
5-Bromo-2-fluoropyridine is a halogenated pyridine that has been used as a molecular scaffold for many Active Pharmaceutical Ingredients (APIs) such as Neuropeptide Y Receptor Y5 Inhibitors, SARS-CoV-2 Major Protease Inhibitors, and Indoleamine-2,3-Dioxygenase-1 Inhibitors in cancer immunotherapy. 5-Bromo-2-fluoropyridine is also an ideal building block for semiconductors, due to its aromaticity and electron deficiency. A host material of 5-(5-(2,4,6-triiso-propylphenyl)pyridin-2-yl)-5H-benzo[d]benzo-[4,5]imidazo[1,2-a]imidazole is synthesized from 5-bromo-2-fluoropyridine for OLED applications.
Chemische Eigenschaften
5-Bromo-2-fluoropyridine is a colourless or yellowish liquid compound with a density of 1.71 g/cm3 at 25° C; boiling point of 162-164° C (lit.) at 750 mmHg; stored at room temperature.
Verwenden
5-Bromo-2-fluoropyridine is used in the synthesis of heteroaromatic and aniline derivatives of piperidines as potent ligands used for vesicular acetylcholine transport. Also used in the synthesis of benzofurano[3,2-d]pyrimidin-2-one derived inhbitors.
Synthese

403-45-2

766-11-0

A. Synthesis of 2-fluoro-5-bromopyridine: 2.2 g (15.6 mmol) of 6-fluoronicotinic acid, 5.1 g of red mercuric oxide (HgO) and 1.2 ml of bromine were dissolved in 100 ml of carbon tetrachloride (CCl4) to form a suspension. The reaction was carried out under reflux conditions for 5 hours and subsequently cooled to room temperature. The reaction mixture was filtered through diatomaceous earth and the filtrate was concentrated under vacuum. The residue was dissolved in hexane, filtered again and the filtrate was concentrated under vacuum to give 1.73 g (63% yield) of 2-fluoro-5-bromopyridine, the product being a light yellow oil.
Einzelnachweise
[1] Patent: US5618821, 1997, A

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