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Methyl 2-chloroisonicotinate

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Methyl 2-chloroisonicotinate manufacturers

Methyl 2-chloroisonicotinate Basic information
Product Name:Methyl 2-chloroisonicotinate
Synonyms:2-CHLORO-ISONICOTINIC ACID METHYL ESTER;Methyl 2-chloroisonicotinate ,98%;4-Pyridinecarboxylic acid, 2-chloro-, methyl ester;BUTTPARK 91\04-05;METHYL 2-CHLORO-4-PYRIDINECARBOXYLATE;Methyl 2-chloroisonicotin...;2-Chloroisonicotinic Acid Methyl Ester Methyl 2-Chloro-4-pyridinecarboxylate 2-Chloro-4-pyridinecarboxylic Acid Methyl Ester;Methyl 2-chloropyridine-4-carboxylate, 2-Chloro-4-(methoxycarbonyl)pyridine
CAS:58481-11-1
MF:C7H6ClNO2
MW:171.58
EINECS:
Product Categories:alkyl chloride|carboxylic ester;Picolinic acid series;blocks;Carboxes;Pyridines;Esters;Pyridine
Mol File:58481-11-1.mol
Methyl 2-chloroisonicotinate Structure
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)
Fp >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 Reference58481-11-1(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 Information
ProviderLanguage
SigmaAldrich English
Methyl 2-chloroisonicotinate Usage And Synthesis
Chemical PropertiesWhite to light brown solid
Synthesis
Methanol

67-56-1

2-Chloro-4-pyridinecarboxylic acid

6313-54-8

METHYL 2-CHLOROISONICOTINATE

58481-11-1

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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