2-Amino-5-bromo-4-methyl-3-nitropyridine Chemical Properties

Melting point:

160-164

Boiling point:

314.1±37.0 °C(Predicted)

Density 

1.795±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

pka

0.78±0.50(Predicted)

form 

powder to crystal

color 

Light yellow to Brown

CAS DataBase Reference

100367-40-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2933399990

2-Amino-5-bromo-4-methyl-3-nitropyridine Usage And Synthesis

Uses

2-Amino-5-bromo-4-methyl-3-nitropyridine is a pyridine derivative. Its molecular structure contains reactive groups of bromine atoms, amino groups and nitric acid, which can be used in a variety of chemical reactions, such as substitution, condensation, and nitro-reduction reactions. It is mainly used in organic synthesis or pharmaceutical intermediates.

Synthesis

Part A: The reaction vessel was first purged with inert gas under inert gas protection. 7.50L of acetic acid was added to the vessel and the temperature was maintained at 20-25°C. Subsequently, 1.00 kg of 4-methyl-3-nitropyridin-2-amine (compound of formula 1) was added to form a yellow suspension. Next, 1.07 kg of sodium acetate was added and the reaction mixture changed to a very thick yellow suspension and a slight exothermic phenomenon was observed. After raising the reaction temperature to about 27°C, the reaction was cooled to 15-20°C and samples were taken for analysis by high pressure liquid chromatography (HPLC). A solution of 1.15 kg of bromine (1.1 eq.) with 2.5 L of acetic acid was prepared and a 10/11 portion (i.e., 1.0 eq.) was added dropwise to the reaction vessel over a period of 10-15 minutes, maintaining the temperature at 15-20°C. A slight exotherm was observed during the dropwise addition and proper cooling was required to maintain the temperature not exceeding 20°C. HPLC analysis was performed immediately after dropwise addition and monitored again after 60 minutes and less than 10% of the starting material was found to be remaining. The remaining bromine solution was added and the reaction was continued with stirring for 30-60 minutes until the reaction was complete. At the end of the reaction, 10.0 L of ice water was added and cooled to 11°C to form a suspension. After continued stirring for 30-60 minutes, the product was collected by filtration and washed with 3 x 2.50 L of ice water. The product was dried at 40°C to constant weight to give 1.45 kg of yellow crystals in 96% yield. The melting point of the product was 132 °C. IR (KBr, cm^-1): 1633, 1581, 1538, 1512, 1458, 1377, 1344, 1321, 1244, 869, 779. 1H-NMR (CDCl3, δ, ppm): 2.55 (s, 3H), 5.85 (bs, 2H), 8.25 (s, 1H) .13C-NMR (CDCl3, δ, ppm): 20.81, 112.14, 144.49, 151.91, 153.78 (2C).MS (M+1): 232.Elemental Analysis: C6H6BrN3O2 Calculated Values: C, 31.05; H, 2.60; N, 18.11; Br, 34.43.Measured Values. 30.95; H, 2.42; N, 17.45; Br, 34.80.

References

[1] Patent: US2006/293304, 2006, A1. Location in patent: Page/Page column 28-29
[2] Patent: US2007/32503, 2007, A1. Location in patent: Page/Page column 8-9; 10
[3] Patent: WO2014/125408, 2014, A2. Location in patent: Page/Page column 38

2-Amino-5-bromo-4-methyl-3-nitropyridine(100367-40-6)Related Product Information

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