3,5-DICHLORO-4-FORMYL PYRIDINE Chemical Properties

Melting point:

75-79 °C (lit.)

Boiling point:

242.4±35.0 °C(Predicted)

Density 

1.488±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

-0.42±0.10(Predicted)

color 

White to Brown

InChIKey

RBFNWOINNIOZKR-UHFFFAOYSA-N

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2933399990

MSDS

• Language:English Provider:SigmaAldrich

3,5-DICHLORO-4-FORMYL PYRIDINE Usage And Synthesis

Uses

3,5-Dichloroisonicotinaldehyde is an aldehyde compound that can be synthesized with heteroarylsulfonamides to form heteroarylsulfonylcarboxamides[1].

Synthesis

Diisopropylamine (33.6 mL, 0.24 mol) was dissolved in tetrahydrofuran (400 mL) under argon protection and cooled to -65 °C. The solution of 1.6 M n-butyllithium in hexane (156 mL) was added slowly. A hexane solution (156 mL) of 1.6 M n-butyllithium was slowly added. after 20 min, a solution of 3,5-dichloropyridine (29.6 g, 0.20 mol) in tetrahydrofuran (150 mL) was added dropwise, and stirring was continued for 30 min. Subsequently, a tetrahydrofuran (50 mL) solution of dimethylformamide (23.2 mL, 0.30 mol) was added, kept at a constant temperature and stirred for 1 hour. The reaction mixture was poured into 5% aqueous ammonium chloride solution (1,000 mL) and extracted with ethyl acetate. The organic layer was washed sequentially with water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford 3,5-dichloropyridine-4-carbaldehyde (27.2 g, 77% yield).1H-NMR (CDCl3) δ: 8.63 (2H, s), 10.44 (1H, s).

References

[1] Patent: US5935977, 1999, A
[2] Patent: EP1270577, 2003, A1

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