2-Chloro-5-methyl-3-nitropyridine Chemical Properties

Melting point:

45-50 °C

Boiling point:

290.8±35.0 °C(Predicted)

Density 

1.406±0.06 g/cm3(Predicted)

storage temp. 

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

form 

powder to crystal

pka

-2.20±0.10(Predicted)

color 

White to Orange to Green

Sensitive 

Hygroscopic

BRN 

138198

CAS DataBase Reference

23056-40-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-21/22-41-37/38-22

Safety Statements 

36/37/39-26-36-39

RIDADR 

2811

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333990

MSDS

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2-Chloro-5-methyl-3-nitropyridine Usage And Synthesis

Application

2-Chloro-5-methyl-3-nitropyridine is an organic intermediate that can be obtained by chlorination of 5-methyl-3-nitropyridine-2(1H)-one. The chlorination reagent can be selected from phosphorus oxychloride. It can be used as an organic synthesis intermediate and a pharmaceutical intermediate, mainly in laboratory research and development processes and chemical production processes.

Chemical Properties

Beige powder

Synthesis

a) General procedure for the synthesis of 2-chloro-5-methyl-3-nitropyridine: 5-methyl-3-nitropyridin-2-ol (5 g, 32.4 mmol) and benzyltrimethylammonium chloride (3.01 g, 16.2 mmol) were dissolved in acetonitrile, followed by addition of phosphorochloridic acid (9.0 ml, 97.2 mmol). The reaction mixture was stirred at 80 °C for 6 hours. After completion of the reaction, the mixture was cooled to room temperature and slowly poured into ice water to quench the reaction. The aqueous phase was extracted with dichloromethane and the organic layers were combined, washed with saturated brine solution and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using dichloromethane as eluent. The fraction containing the target compound was collected and concentrated under reduced pressure to give 2-chloro-5-methyl-3-nitropyridine as a yellow solid (5.39 g, 97% yield). The product was confirmed by 1H-NMR (CDCl3, 300 MHz) and mass spectrometry (ESI): 1H-NMR δ= 8.45 (d, 1H, J = 2.3Hz), 8.04 (d, 1H, J = 2.3Hz), 2.46 (s, 3H); MS (ESI) m/z: 173.0 ([M+H]+).

References

[1] Patent: US2011/28467, 2011, A1. Location in patent: Page/Page column 51
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 5, p. 985 - 995
[3] Patent: EP2366691, 2011, A1. Location in patent: Page/Page column 9
[4] Patent: WO2015/73528, 2015, A1. Location in patent: Page/Page column 118
[5] Journal of the American Chemical Society, 1951, vol. 73, p. 3504

2-Chloro-5-methyl-3-nitropyridine(23056-40-8)Related Product Information

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