2,5-Dichloropyridine Chemical Properties

Melting point:

59-62 °C (lit.)

Boiling point:

190-191 °C

Density 

1.5159 (rough estimate)

refractive index 

1.5500 (estimate)

Flash point:

112 °C

storage temp. 

Inert atmosphere,Room Temperature

pka

-2.25±0.10(Predicted)

form 

Crystalline Solid

color 

White to slightly yellow

Water Solubility 

insoluble

BRN 

108886

InChI

InChI=1S/C5H3Cl2N/c6-4-1-2-5(7)8-3-4/h1-3H

InChIKey

GCTFDMFLLBCLPF-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

16110-09-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-37/39-36

RIDADR 

UN2811

WGK Germany 

3

RTECS 

US8225000

Hazard Note 

Harmful

HazardClass 

IRRITANT

HazardClass 

6.1

HS Code 

29333990

MSDS

• Language:English Provider:2,5-Dichloropyridine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,5-Dichloropyridine Usage And Synthesis

Uses

2,5-Dichloropyridine is a reagent used in chemical synthesis. It has been used to synthesize 4-benzodiazepine-2,5 diones as Hdm2 antagonists and inhibitors of ERK protein kinase.

Chemical Properties

white to slightly yellow crystalline solid

Uses

2,5-Dichloropyridine was used in the synthesis of 6-halo-pyridin-3-yl boronic acids and esters. It undergoes cross-coupling reaction with arylboronic acids in the presence of [1,4-bis-(diphenylphosphine)butane]palladium (II) dichloride as catalyst.

Synthesis Reference(s)

Synthetic Communications, 20, p. 2971, 1990 DOI: 10.1080/00397919008051514

General Description

2,5-Dichloropyridine undergoes cross-coupling reaction with arylboronic acids in the presence of [1,4-bis-(diphenylphosphine)butane]palladium (II) dichloride as catalyst.

Synthesis

General procedure for the synthesis of 2,5-dichloropyridine from 2,5-dibromopyridine: Catalyst 1 (10 mol%), 2,5-dibromopyridine (1.0 mmol), tetramethylammonium chloride (Me4NCl, 2.0 mmol), and ethanol (EtOH, 2.0 mL) were added to a Schlenk tube under nitrogen protection. Schlenk tubes were sealed using polytetrafluoroethylene (Teflon) valves and the reaction mixture was stirred at 100 °C. The reaction process was monitored by gas chromatography (GC) analysis. After completion of the reaction, the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent ratio petroleum ether/ethyl acetate = 10:1) to give 2,5-dichloropyridine. The yield of the product was determined by high-resolution gas chromatography-mass spectrometry (GC-MS) analysis and the structure was confirmed by comparing its physical properties and spectral data with known compounds.

References

[1] Applied Catalysis A: General, 2014, vol. 472, p. 178 - 183
[2] Chemical Communications, 2012, vol. 48, # 76, p. 9468 - 9470

2,5-Dichloropyridine(16110-09-1)Related Product Information

• 5-Amino-2-methylpyridine
• 2-Chloro-5-chloromethylpyridine
• 2-(Hydroxymethyl)pyridine
• 2,6-Lutidine
• 1,2-Dichloroethane
• 2,5-Dimethylpyridine
• 2,3-DICHLOROPYRIDINE
• Methyl 2,3,5,6-tetrachloro-4-pyridyl sulfone
• Triclopyr
• Picloram
• Chlorpyrifos
• 2,3,5,6-Tetrachloropyridine
• 2,6-Dichloropyridine
• Dichloropyridine,98%
• 2,3,5,6-Tetrachloropyridine-4-thiol
• Pentachloropyridine
• 2,3,5-Trichloropyridine
• Clopyralid