4,6-Dichloro-5-nitronicotinic acid ethyl ester

4,6-Dichloro-5-nitronicotinic acid ethyl ester Property

Melting point:

36-38°

Boiling point:

352.9±37.0 °C(Predicted)

Density 

1.533±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-3.86±0.10(Predicted)

Appearance

Off-white to light brown Solid

Safety

HazardClass 

IRRITANT

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H227Combustible liquid

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

4,6-Dichloro-5-nitronicotinic acid ethyl ester Chemical Properties,Usage,Production

Synthesis

Step 3: Preparation of ethyl 4,6-dichloro-5-nitronicotinate (16) Ethyl 4,6-dihydroxy-5-nitronicotinate (15) (20.0 g, 87.7 mmol) was dissolved in phosphoryl chloride (80 mL, 874 mmol). The reaction mixture was stirred at 80 °C for 24 hours. Upon completion of the reaction, about half the volume of phosphoryl chloride was evaporated under reduced pressure. The residue was slowly poured into ice water and extracted twice with ethyl acetate. The organic phases were combined and washed sequentially with aqueous sodium carbonate, water and saturated saline. The organic layers were dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a brown oily crude product. The crude product was purified by silica gel column chromatography with petroleum ether/ethyl acetate (3:1, v/v) as eluent to give white crystalline solid 16 (14.2 g, yield 61.1%). The melting point of the product was 36-38 °C. 1H NMR (300 MHz, DMSO-d6) δ: 9.07 (s, 1H), 4.39 (q, J = 6.0 Hz, 2H), 1.34 (t, J = 6.0 Hz, 3H). m/z MS (ESI (+) 70 V): 264 [M + H]+.

References

[1] Journal of Heterocyclic Chemistry, 1993, vol. 30, # 4, p. 855 - 859
[2] Patent: WO2008/17696, 2008, A1. Location in patent: Page/Page column 51
[3] Patent: WO2009/106419, 2009, A1. Location in patent: Page/Page column 79
[4] Patent: WO2008/17696, 2008, A1. Location in patent: Page/Page column 51
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 20, p. 6551 - 6559