METHYL 2-CHLOROISONICOTINATE Chemical Properties

Melting point:

32-36 °C

Boiling point:

70°C/0.1mmHg(lit.)

Density 

1.294±0.06 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,2-8°C

pka

-1.15±0.10(Predicted)

form 

powder to lump to clear liquid

color 

White or Colorless to Yellow

CAS DataBase Reference

58481-11-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41

Safety Statements 

26-36/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

METHYL 2-CHLOROISONICOTINATE Usage And Synthesis

Chemical Properties

White to light brown solid

Synthesis

2-Chloroisonicotinic acid (5.10 g, 32.38 mmol) was dissolved in methanol (150 mL) and thionyl chloride (12 mL) was added slowly. The reaction mixture was stirred at 70 °C for 5 h. After completion of the reaction, the reaction solution was concentrated under reduced pressure by rotary evaporator. The concentrated residue was dissolved in dichloromethane (250 mL), washed sequentially with 10% aqueous potassium carbonate (2×150 mL), dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by rotary evaporation to afford methyl 2-chloropyridine-4-carboxylate (SLA 07150) as a yellow solid (5.06 g, 91% yield).The molecular weight of SRA 07150 was 171.58; melting point was 33.0 °C; thin layer chromatography (TLC) Rf value was 0.80 (unfolding reagent ratio methanol:dichloromethane=10:90).1H-NMR (CDCl3, δ): 3.98 (s, 3H, CH3), 7.78 (dd, 1H, J=5.1 Hz, J=1.3 Hz, ArH), 7.89 (d, 1H, J= 0.6 Hz, ArH), 8.55 (dd, 1H, J=5.1 Hz, J=0.6 Hz, ArH).

References

[1] Patent: WO2008/11478, 2008, A2. Location in patent: Page/Page column 76
[2] Patent: WO2016/154241, 2016, A1. Location in patent: Paragraph 578; 579
[3] Patent: US2008/167321, 2008, A1. Location in patent: Page/Page column 14
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2785 - 2790
[5] Patent: EP1754706, 2007, A1. Location in patent: Page/Page column 76

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