2-Chloro-5-fluoropyridine Chemical Properties

Melting point:

19℃

Boiling point:

74 °C / 38mmHg

Density 

1.297 g/mL at 25 °C

refractive index 

n20/D 1.503

Flash point:

108 °C

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

powder to lump to clear liquid

pka

-2.20±0.10(Predicted)

color 

White or Colorless to Light yellow

InChI

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

InChIKey

QOGXQLSFJCIDNY-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C(F)C=C1

CAS DataBase Reference

31301-51-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

10-22-37/38-41-36/37/38

Safety Statements 

26-36/39-36

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

3

PackingGroup 

III

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

2-Chloro-5-fluoropyridine Usage And Synthesis

Chemical Properties

Light yellow powder

Uses

2-Chloro-5-fluoropyridine, is the intermediate used for the synthesis of pharmaceuticals agents and biologically active compounds, such as pyrazol-3-ylamino pyrazines as novel JAK2 inhibitors.

Synthesis

The general procedure for the synthesis of 2-chloro-5-fluoropyridine from 2-chloro-5-aminopyridine is as follows: in a 25-mL three-necked flask equipped with a reflux condenser, thermocouple, and stirring system, 1 g (7.78 mmol) of 2-chloro-5-aminopyridine was dissolved in 14.3 g of o-dichlorobenzene, and added dropwise over a 5-min period of 5 min at room temperature to 1.64 g (11.5 mmol, 1.47 molar equivalents) of the boron trifluoride ethyl ether complex. Upon completion of the dropwise addition, the reaction solution was beige in color and accompanied by the formation of a precipitate. Subsequently, the reaction system was heated to 105 °C and maintained for 20 minutes before 1.05 g (9.2 mmol, 1.18 mole equivalents, 90% purity) of tert-butyl nitrite was added to 5.0 g of o-dichlorobenzene at a controlled titration rate of 25 ml/hr. The reaction was kept at 105 °C and continued for 25 min, after which the heating was stopped. The yield of 2-chloro-5-fluoropyridine was 36% as determined by 19F NMR.

References

[1] Patent: US2007/276168, 2007, A1. Location in patent: Page/Page column 9

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