ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Fluoropyridine 2,6-Difluoropyridine

2,6-Difluoropyridine

Product Name2,6-Difluoropyridine
CAS1513-65-1
MFC5H3F2N
MW115.08
EINECS216-152-8
MOL File1513-65-1.mol

Chemical Properties

Boiling point	124.5 °C/743 mmHg (lit.)
Density	1.268 g/mL at 25 °C (lit.)
refractive index	n20/D 1.437(lit.)
Flash point	93 °F
storage temp.	Inert atmosphere,2-8°C
solubility	Not miscible or difficult to mix.
form	Liquid
pka	-6.09±0.10(Predicted)
Specific Gravity	1.268
color	Clear purple-red
BRN	1422549
Dielectric constant	107.8
InChI	1S/C5H3F2N/c6-4-2-1-3-5(7)8-4/h1-3H
InChIKey	MBTGBRYMJKYYOE-UHFFFAOYSA-N
SMILES	Fc1cccc(F)n1
CAS DataBase Reference	1513-65-1(CAS DataBase Reference)
NIST Chemistry Reference	2,6-Difluoropyridine(1513-65-1)

Safety Information

Hazard Codes	Xi,T,F
Risk Statements	10-36/37/38
Safety Statements	16-26-36/37/39-37/39
RIDADR	UN 1993 3/PG 3
WGK Germany	3
F	10
Hazard Note	Toxic
HazardClass	3
PackingGroup	III
HS Code	29333999
Storage Class	3 - Flammable liquids
Hazard Classifications	Eye Irrit. 2 Flam. Liq. 3 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
2,6-Difluoropyridine	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

Colorless to light yellow liquid

Uses

2,6-Difluoropyridine has been used in the preparation of poly(pyridine ether)s via polycondensation with silylated 1,1,1-tris(4-hydroxyphenyl)ethane.

General Description

Lithium diisopropylamide (LDA)-mediated ortholithiations of 2,6-difluoropyridine in tetrahydrofuran at -78°C has been studied using a combination of IR and NMR spectroscopic and computational methods. Polycondensation of bistrimethylsilyl derivatives of various diphenols with 2,6-difluoropyridine in N-methylpyrrolidone in the presence of K₂CO₃ has been investigated.

Synthesis

2402-78-0

1513-65-1

General procedure for the synthesis of 2,6-difluoropyridine from 2,6-dichloropyridine: In a desiccator, accurately weigh anhydrous NMe4F (18.6 mg, 0.2 mmol, 2 eq.) and 2,6-dichloropyridine (0.1 mmol, 1 eq.) in a 4 mL vial fitted with a microstirring bar. DMF (0.5 mL) was added, the vial was removed from the desiccator, and the reaction was stirred at room temperature for 24 hours. Upon completion of the reaction, the reaction mixture was cooled to room temperature and the internal standard (1,3,5-trifluorobenzene, 100 μL 0.5 M toluene solution) was added. Aliquots were taken for 59F NMR spectroscopy and GC-MS analysis.

References

[1] Patent: US4071521, 1978, A
[2] Angewandte Chemie - International Edition, 2006, vol. 45, # 17, p. 2720 - 2725
[3] Organic Letters, 2015, vol. 17, # 8, p. 1866 - 1869
[4] Journal of Organic Chemistry, 2015, vol. 80, # 24, p. 12137 - 12145
[5] Patent: WO2017/24167, 2017, A1. Location in patent: Page/Page column 29; 33; 35

2,6-Difluoropyridine

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

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