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2-METHOXY-3,5-DIBROMO-PYRIDINE

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2-METHOXY-3,5-DIBROMO-PYRIDINE Basic information

Product Name:
2-METHOXY-3,5-DIBROMO-PYRIDINE
Synonyms:
  • 3,5-DIBROMO-2-METHOXYPYRIDINE
  • 2-METHOXY-3,5-DIBROMO-PYRIDINE
  • 2-METHOXY-5-PICOLINE (2-METHOXY-5-METHYLPYRIDINE)
  • Pyridine, 3,5-dibroMo-2-Methoxy-
  • 3,5-DibroMo-2-Methoxypyridine
  • 3-methyl-5-nitropyridin-3-amine
  • 2-METHOXY-3,5-DIBROMO-PYRIDINE ISO 9001:2015 REACH
  • Dopaquinone Monomer
CAS:
13472-60-1
MF:
C6H5Br2NO
MW:
266.92
Product Categories:
  • Heterocycle-Pyridine series
  • Pyridine
Mol File:
13472-60-1.mol
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2-METHOXY-3,5-DIBROMO-PYRIDINE Chemical Properties

Melting point:
46-51℃
Boiling point:
235.7±35.0 °C(Predicted)
Density 
1.919±0.06 g/cm3(Predicted)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
soluble in Methanol
form 
powder to crystal
pka
-1.31±0.20(Predicted)
color 
White to Orange to Green
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Safety Information

Hazard Codes 
Xi,Xn
Risk Statements 
36/37/38-41-22
Safety Statements 
26-36-45
RIDADR 
UN 2811
WGK Germany 
1
Hazard Note 
Harmful
HazardClass 
IRRITANT
HS Code 
2933399990
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2-METHOXY-3,5-DIBROMO-PYRIDINE Usage And Synthesis

Synthesis

13472-85-0

13472-60-1

The general procedure for the synthesis of 2-methoxy-3,5-dibromopyridine from 5-bromo-2-methoxypyridine was as follows: bromine (17.8 g, 111 mmol) was slowly added to a mixed solution containing 5-bromo-2-methoxypyridine (12.0 g, 63.8 mmol), sodium acetate (5.23 g, 63.8 mmol) and acetic acid (65 mL). The reaction mixture was stirred at 80 °C for 4 hours, followed by continued stirring at room temperature for 12 hours. After completion of the reaction, the mixture was diluted with ether and washed sequentially with water, saturated sodium bicarbonate solution and brine. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography with the eluent being a petroleum ether solution of 1-5% ethyl acetate to give 10.6 g of the target product 2-methoxy-3,5-dibromopyridine. The product was characterized by 1H NMR (300 MHz, DMSO-d6) with chemical shifts of 8.20-8.40 (m, 2H) and 3.92 (s, 3H).

References

[1] Patent: US2010/81673, 2010, A1. Location in patent: Page/Page column 14
[2] Patent: US2015/210671, 2015, A1. Location in patent: Paragraph 0173; 0181; 0182
[3] Patent: US9145393, 2015, B2. Location in patent: Page/Page column 37; 38

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