Methyl 2,6-dichloronicotinate

Methyl 2,6-dichloronicotinate Property

Melting point:

56-60 °C(lit.)

Boiling point:

270.5±35.0 °C(Predicted)

Density 

1.426±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

-4.55±0.10(Predicted)

color 

White to Light yellow

Sensitive 

Air Sensitive

λmax

276nm(lit.)

InChI

InChI=1S/C7H5Cl2NO2/c1-12-7(11)4-2-3-5(8)10-6(4)9/h2-3H,1H3

InChIKey

IFVVGOJYWCHRCT-UHFFFAOYSA-N

SMILES

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

Safety

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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.

Methyl 2,6-dichloronicotinate Chemical Properties,Usage,Production

Uses

Replacement of chlorides with fluorides using anhydrous nucleophilic fluoride salts generated from potassium fluoride and an arene transfer agent.

Synthesis

General procedure for the synthesis of methyl 2,6-dichloronicotinate from methanol and 2,6-dichloronicotinic acid: to a solution of 2,6-dichloronicotinic acid (5.0 g, 26 mmol) in methanol (100 mL) was slowly added thionyl chloride (0.1 mL). The reaction mixture was heated to reflux and kept reacting overnight. Upon completion of the reaction, the solvent was removed by rotary evaporator. The residue was dissolved in ethyl acetate and washed sequentially with saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated to give methyl 2,6-dichloronicotinate (5.37 g, 100% yield) as a white solid.1H NMR (300 MHz, CDCl3) δ 8.13 (d, J=8.1 Hz, 1H), 7.33 (d, J=8.1 Hz, 1H), 3.94 (s, 3H).

References

[1] Patent: US2005/119251, 2005, A1. Location in patent: Page/Page column 20; 22
[2] Patent: WO2006/14168, 2006, A1. Location in patent: Page/Page column 47
[3] Patent: WO2008/16643, 2008, A2. Location in patent: Page/Page column 233
[4] Patent: WO2006/88836, 2006, A2. Location in patent: Page/Page column 78
[5] Patent: WO2006/88920, 2006, A1. Location in patent: Page/Page column 133-134