Ethyl 4,6-dichloronicotinate Chemical Properties

Melting point:

32-34°

Boiling point:

85°C/0.01mmHg(lit.)

Density 

1.367±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in methanol.

pka

-1.24±0.10(Predicted)

form 

Liquid

color 

Yellow

InChI

InChI=1S/C8H7Cl2NO2/c1-2-13-8(12)5-4-11-7(10)3-6(5)9/h3-4H,2H2,1H3

InChIKey

AAUBVINEXCCXOK-UHFFFAOYSA-N

SMILES

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

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36

HazardClass 

IRRITANT

HS Code 

29339900

Ethyl 4,6-dichloronicotinate Usage And Synthesis

Uses

Ethyl 4,6-Dichloronicotinate acts as a reactant in the preparation of (acylamino)aminonaphthyridinones as novobiocin analogs and Hsp90 inhibitors, their antitumor activities in human breast cancer cell lines, and the effects on aptoptosis and cell cycle advancement of selected compounds.

Chemical Properties

White solid

Uses

Ethyl 4,6-dichloronicotinate is an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals, and dyestuffs. It is also used as a fine chemical intermediate. Ethyl-4,6-dichloronicotinate could be used as a starting material to synthesize 6-chlorothieno[3,2-c]pyridine-2-carbohydrazide-hydrazone subsidiaries[1].

Synthesis

The general procedure for the synthesis of ethyl 4,6-dichloronicotinate from ethyl 4,6-dihydroxynicotinate was as follows: ethyl 4,6-dihydroxynicotinate (60 g, 0.328 mol) was slowly added to phosphorus triclosan (POCl3, 500 mL), followed by heating and refluxing for 2 hours. Upon completion of the reaction, the excess phosphorous trichloride was removed by distillation under reduced pressure. The residue was carefully poured into ice water, stirred for 30 min, and then extracted with ethyl acetate (EtOAc, 3 times). The organic phases were combined, washed with saturated brine, dried over anhydrous magnesium sulfate (MgSO4) and finally concentrated under vacuum to give ethyl 4,6-dichloronicotinate (65 g, 90% yield). The product was identified by 1H NMR (300 MHz, DMSO-d6): δ 8.80 (s, 1H), 7.95 (s, 1H), 4.34 (q, J=6.9 Hz, 2H), 1.31 (t, J=6.9 Hz, 3H); Mass Spectra (ESI) m/z: 220.1 [M+H]+.

References

[1] N. Rao, K. Prasad, M. Rao. “Synthesis and Antibacterial Evaluation of Hydrazone Derivatives Bearing 6-Chlorothieno[3,2-c]pyridine Moiety.” Asian Journal of Chemistry 1 1 (2019).

Ethyl 4,6-dichloronicotinate(40296-46-6)Related Product Information

• Ethyl acetoacetate
• 4,6-Dichloronicotinic acid
• 6-Chloronicotinic acid
• Ethyl pyruvate
• Ethyl acrylate
• Thionyl chloride
• Ethyl oleate
• Ethyl acetate
• Ethanol
• 2-Chloronicotinic acid
• Ethyl nicotinate
• 2,5-Dichloronicotinic acid
• 2,6-Dichloronicotinic acid
• Tris(trimethylsilyl)phosphate
• 5,6-Dichloronicotinic acid
• Ethyl formate
• Ethyl cyanoacetate
• Ethylparaben