2 6-DICHLOROPYRIDINE-3-CARBOXALDEHYDE Chemical Properties

Melting point:

74-75 °C (lit.)

Boiling point:

95°C/3mmHg(lit.)

Density 

1.488±0.06 g/cm3(Predicted)

storage temp. 

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

form 

powder to crystal

pka

-4.52±0.10(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C6H3Cl2NO/c7-5-2-1-4(3-10)6(8)9-5/h1-3H

InChIKey

HWTMRGXKSANEDO-UHFFFAOYSA-N

SMILES

C1(Cl)=NC(Cl)=CC=C1C=O

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38-43

Safety Statements 

26-36/37

RIDADR 

2811

WGK Germany 

3

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

2933399990

2 6-DICHLOROPYRIDINE-3-CARBOXALDEHYDE Usage And Synthesis

Synthesis

The general procedure for the synthesis of 2,6-dichloro-3-pyridinecarboxaldehyde from 2,6-dichloro-3-hydroxymethylpyridine was as follows: to a solution of (2,6-dichloropyridin-3-yl)methanol (1.0 g, 5.62 mmol) in dichloromethane (10 ml) was added Dess-Martin reagent (4.8 g, 11.24 mmol) at 26 °C. After addition, the reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the reaction was quenched by addition of 5% Na2S2O3 aqueous solution and stirring was continued for 30 min. The reaction mixture was extracted with dichloromethane (2 x 30 ml). The organic layers were combined and washed sequentially with saturated Na2S2O3 solution (50 ml), brine (30 ml), dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford the crude 2,6-dichloro-3-pyridinecarboxaldehyde (800 mg, 80% yield), which was used directly in the next step of the reaction. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 10.38 (s, 1H), 8.19 (d, J = 8.0Hz, 1H), 7.44 (d, J = 8.0Hz, 1H).

References

[1] Patent: WO2014/100695, 2014, A1. Location in patent: Paragraph 00409
[2] Journal of Organic Chemistry, 1982, vol. 47, # 14, p. 2800 - 2802
[3] Patent: WO2006/44454, 2006, A1. Location in patent: Page/Page column 62
[4] Patent: US3974166, 1976, A

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• N-[(2,6-DICHLORO-4-METHYL-3-PYRIDYL)CARBONYL]-N'-MORPHOLINOUREA
• N-[(2,6-DICHLORO-4-METHYL-3-PYRIDYL)CARBONYL]-N'-(2,5-DICHLOROPHENYL)UREA
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