3-Chloro-2-fluoro-pyridine

3-Chloro-2-fluoro-pyridine Property

Boiling point:

162℃

Density 

1.33

Flash point:

52°(126°F)

refractive index 

1.5030

storage temp. 

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

form 

clear liquid

pka

-2.71±0.10(Predicted)

color 

Colorless to Almost colorless

InChI

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

InChIKey

IHGMHTQDGNVKTA-UHFFFAOYSA-N

SMILES

C1(F)=NC=CC=C1Cl

CAS DataBase Reference

1480-64-4(CAS DataBase Reference)

Safety

Hazard Codes 

T,Xn

Risk Statements 

22-37/38-41-34-20/21/22-10

Safety Statements 

26-39-45-36/37/39

RIDADR 

2924

HazardClass 

3

PackingGroup 

III

HS Code 

29333990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H226Flammable liquid and vapour

H302Harmful if swallowed

H312Harmful in contact with skin

H314Causes severe skin burns and eye damage

H315Causes skin irritation

H318Causes serious eye damage

H319Causes serious eye irritation

H332Harmful if inhaled

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

3-Chloro-2-fluoro-pyridine Chemical Properties,Usage,Production

Uses

3-Chloro-2-fluoropyridine is used as a reactant in the synthesis of several compounds with therapeutic potential.

Synthesis

GENERAL METHOD: To a solution of 2,3-dichloropyridine (1.00 g, 6.76 mmol) in dimethyl sulfoxide (DMSO, 33.8 mL) was added cesium fluoride (CsF, 2.053 g, 13.51 mmol) at room temperature. The reaction mixture was stirred in air at 110 °C for 20 hours. After completion of the reaction, the reaction mixture was quenched with ice water and extracted with ethyl acetate (EtOAc). The organic layer was separated, washed sequentially with water and saturated brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using ethyl acetate (EtOAc) in hexane as eluent to afford 3-chloro-2-fluoropyridine (0.639 g, 4.86 mmol, 71.9% yield) as a colorless oil. Compounds 3B'-8B' were prepared by a method similar to the synthetic procedure for compound 2B'.

References

[1] Tetrahedron Letters, 2015, vol. 56, # 44, p. 6043 - 6046
[2] Angewandte Chemie - International Edition, 2006, vol. 45, # 17, p. 2720 - 2725
[3] Patent: EP1595867, 2005, A1. Location in patent: Page/Page column 33-34
[4] Organic Letters, 2015, vol. 17, # 8, p. 1866 - 1869
[5] Patent: EP1726590, 2006, A1. Location in patent: Page/Page column 56