3,5-DIBROMO-6-CHLOROPYRAZIN-2-AMINE Chemical Properties

Boiling point:

324.0±37.0 °C(Predicted)

Density 

1.237

storage temp. 

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

pka

-1.51±0.10(Predicted)

Appearance

Off-white to light brown Solid

3,5-DIBROMO-6-CHLOROPYRAZIN-2-AMINE Usage And Synthesis

Synthesis

Synthesis Example 1 Preparation of 2-amino-3,5-dibromo-6-chloropyrazine (4): To a solution of 2-amino-6-chloropyrazine (3) (8.00 g, 61.8 mmol) in acetonitrile (80 mL) was slowly added N-bromosuccinimide (NBS) (27.5 g, 155 mmol) at 0 °C. After addition, the reaction mixture was gradually warmed to room temperature and stirred overnight (18 hours). After completion of the reaction, water was added to the mixture and the product was extracted with ether (3 x 80 mL). The organic phases were combined and washed sequentially with water (1 x 80 mL) and saturated saline (1 x 80 mL), then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate= 3/1, v/v) to afford 2-amino-3,5-dibromo-6-chloropyrazine (4) (16.8 g, 58.5 mmol, 94.7% yield) as a yellow solid. tlc Rf = 0.31 (Expander: n-hexane/ethyl acetate= 4/1, v /v); 1H NMR (500MHz, CDCl3) δ 5.14 (s, 2H); 13C NMR (126MHz, CDCl3) δ 120.7, 122.0, 146.1, 151.0.

References

[1] Patent: US2012/232272, 2012, A1. Location in patent: Page/Page column 18
[2] Organic Letters, 2015, vol. 17, # 15, p. 3888 - 3891
[3] Patent: JP5837973, 2015, B2. Location in patent: Paragraph 0180; 0181
[4] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 12, p. 4271 - 4274
[5] Patent: WO2014/29732, 2014, A1. Location in patent: Page/Page column 88

3,5-DIBROMO-6-CHLOROPYRAZIN-2-AMINE(566205-01-4)Related Product Information

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