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2-Chloro-5-nitronicotinic acid methyl ester

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2-Chloro-5-nitronicotinic acid methyl ester manufacturers

2-Chloro-5-nitronicotinic acid methyl ester Basic information
Product Name:2-Chloro-5-nitronicotinic acid methyl ester
Synonyms:Methyl 2-chloro-5-nitronicotinate 95+%;Methyl 2-chloro-5-nitropyridine-3-carboxylate;Methyl 2-chloro-5-nitropyridine-3-carboxylate, 2-Chloro-3-(methoxycarbonyl)-5-nitropyridine;3-Pyridinecarboxylic acid, 2-chloro-5-nitro-, methyl ester;Methyl 2-chloro-5-nitrosoniacinate;METHYL 2-CHLORO-5-NITRONICOTINATE;2-Chloro-5-nitronicotinic acid methyl ester
CAS:190271-88-6
MF:C7H5ClN2O4
MW:216.58
EINECS:
Product Categories:pyridine series;Boronic Acid;Pyridine
Mol File:190271-88-6.mol
2-Chloro-5-nitronicotinic acid methyl ester Structure
2-Chloro-5-nitronicotinic acid methyl ester Chemical Properties
Boiling point 321.5±37.0 °C(Predicted)
density 1.500±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
pka-5.76±0.10(Predicted)
AppearanceOff-white to yellow Solid
Safety Information
HazardClass IRRITANT
HS Code 2933399990
MSDS Information
2-Chloro-5-nitronicotinic acid methyl ester Usage And Synthesis
Synthesis
Methyl 2-hydroxy-5-nitronicotinate

89910-50-9

2-CHLORO-5-NITRONICOTINIC ACID METHYL ESTER

190271-88-6

To a 25 mL suspension of thionyl chloride of methyl nitrosyl-2-hydroxynicotinate (4.62 g, 23.3 mmol) was added 1 mL of DMF and the reaction mixture was heated to reflux until the reaction was complete as detected by TLC. Subsequently, thionyl chloride was removed by evaporation under reduced pressure and azeotroped twice with toluene to remove residual thionyl chloride. The yellow semi-solid product obtained was cooled in an ice bath and treated with 50 mL of methanol. After stirring for 20 minutes, the mixture was poured into 200 mL of water and extracted with ethyl acetate (2 x 150 mL). The organic phases were combined and washed sequentially with dilute aqueous sodium hydroxide, water and brine, then dried with magnesium sulfate. 5.03 g (99% yield) of methyl 2-chloro-5-nitronicotinate was finally obtained as a yellow oil. Its 1H NMR (400 MHz, deuterated chloroform) data were as follows: δ 4.04 (s, 3H), 8.94 (d, J = 2.78 Hz, 1H), 9.33 (d, J = 2.78 Hz, 1H).

References[1] Patent: US2005/203081, 2005, A1. Location in patent: Page/Page column 9; 26
2-Chloro-5-nitronicotinic acid methyl ester Preparation Products And Raw materials
Raw materialsMethanol-->Methyl 2-hydroxy-5-nitronicotinate-->Thionyl chloride-->N,N-Dimethylformamide
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