2-Chloro-3-fluoropyridine Chemical Properties

Boiling point:

80 °C/80 mmHg (lit.)

Density 

1.323 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.509(lit.)

Flash point:

147 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

clear liquid

pka

-0.05±0.10(Predicted)

color 

Colorless to Almost colorless

BRN 

1363435

InChI

InChI=1S/C5H3ClFN/c6-5-4(7)2-1-3-8-5/h1-3H

InChIKey

SVAZIMBLBHOVIR-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=CC=C1F

CAS DataBase Reference

17282-04-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-41-36/37/38-37/38-23/24/25

Safety Statements 

26-36-45-36/37/39

RIDADR 

2810

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

IRRITANT

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Chloro-3-fluoropyridine Usage And Synthesis

Application

2-Chloro-3-fluoropyridine is a pyridine derivative that can be used as a pharmaceutical intermediate.

Chemical Properties

Colorless to light yellow liquid

Synthesis

General procedure for the synthesis of 2-chloro-3-fluoropyridine from 3-fluoropyridine: n-butyllithium (2.5 M hexane solution, 230 ml, 0.57 mol) was added to a solution of 1,4-diazabicyclo[2.2.2]octane (63.8 g, 0.57 mol) in ether (2.5 L) that had been pre-removed from water by azeotropic boiling, at -20 to -30 °C. After stirring for 1 hour, the temperature was adjusted to -65°C. A solution of 3-fluoropyridine (50.0 g, 0.52 mol) in ether (250 ml) was added dropwise over 10 minutes and the mixture was stirred for another 1 hour. Then an ether (350 ml) solution of hexachloroethane (136.5 g, 0.58 mol) was added dropwise over 15 minutes, keeping the temperature below -60°C, and the mixture was stirred for 2 hours. The reaction was quenched by addition of saturated aqueous NH4Cl solution (250 ml), warmed to ambient temperature and separated. The aqueous phase was extracted with ether (2 x 250 ml) and the combined organic phases were washed with saturated aqueous NH4Cl solution (250 ml), dried over anhydrous MgSO4 and concentrated in vacuum. The residue was diluted with isohexane (150 ml), washed with 2N hydrochloric acid (3 x 100 ml) and then with 37% hydrochloric acid (3 x 50 ml). The acid wash was then extracted with isohexane (3 x 100 ml), alkalized to pH 14 by careful addition of 4N aqueous NaOH (500 ml) and re-extracted with CH2Cl2 (3 x 150 ml). The organic fraction was dried over anhydrous MgSO4 and concentrated in vacuum. The residue was purified by distillation (boiling point 74-82 °C, 1 atm) to give 2-chloro-3-fluoropyridine as a straw-colored oil (42.6 g, 63%).

References

[1] Patent: WO2003/99816, 2003, A1. Location in patent: Page 42-43
[2] Patent: WO2003/99817, 2003, A1. Location in patent: Page 35
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 29, p. 9103 - 9107
[4] Angew. Chem., 2018, vol. 130, p. 9241 - 9245,5
[5] Journal of Medicinal Chemistry, 2004, vol. 47, # 15, p. 3853 - 3864

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