ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Bromopyridine 5-Bromo-2-fluoropyridine

5-Bromo-2-fluoropyridine

Product Name5-Bromo-2-fluoropyridine
CAS766-11-0
MFC5H3BrFN
MW175.99
EINECS629-380-1
MOL File766-11-0.mol

Chemical Properties

Boiling point	162-164 °C750 mm Hg(lit.)
Density	1.71 g/mL at 25 °C(lit.)
refractive index	n20/D 1.5325(lit.)
Flash point	165 °F
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
solubility	DMSO (Slightly), Methanol (Slightly)
pka	-2.79±0.10(Predicted)
form	Liquid
color	Clear colorless yellow
Specific Gravity	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 DataBase Reference	766-11-0(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi,Xn
Risk Statements	36/37/38-22
Safety Statements	26-36/37-37/39
RIDADR	UN2810
WGK Germany	3
Hazard Note	Irritant
HazardClass	6.1
PackingGroup	III
HS Code	29339900
Storage Class	10 - Combustible liquids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
5-Bromo-2-fluoropyridine	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Description

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.

Chemical Properties

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.

Uses

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.

Synthesis

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.

References

[1] Patent: US5618821, 1997, A

Preparation Products And Raw materials

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