3,5-Dibromo-2-hydroxypyrazine Chemical Properties

Melting point:

174-178°C

Density 

2.53±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

8.35±0.60(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C4H2Br2N2O/c5-2-1-7-4(9)3(6)8-2/h1H,(H,7,9)

InChIKey

NHVGHXUOFWEOSN-UHFFFAOYSA-N

SMILES

C1(=O)NC=C(Br)N=C1Br

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-41

Safety Statements 

26-39

WGK Germany 

1

HS Code 

29339900

3,5-Dibromo-2-hydroxypyrazine Usage And Synthesis

Chemical Properties

White solid

Uses

3,5-Dibromo-pyrazinol ,is a pyrazine derivative that can be used as a potential building block in chemical synthesis. It can also be used in SRN1 mechanism in heteroaromatic nucleophilic substitution.

Synthesis

Preparation of compound 36a: 3,5-dibromopyrazin-2-ol To a stirred solution of 3,5-dibromopyrazin-2-amine (30 g, 0.12 mol) in acetic acid (300 mL) was added sulfuric acid (50 mL) dropwise at 15-25 °C. Subsequently, a solution of sodium nitrite (16.6 g, 0.24 mol) in water (100 mL) was added dropwise to the resulting solution over a period of 1.5 hours at 10-15°C. After the dropwise addition was completed, the reaction mixture was continued to be stirred at 10-15 °C for 1 hour. The reaction mixture was poured into water (3L) and extracted with ethyl acetate (1L x 3). The organic layers were combined, washed sequentially with saturated sodium bicarbonate solution (1L×3) and brine (1L), dried with anhydrous sodium sulfate, and concentrated under reduced pressure to afford 3,5-dibromo-2-hydroxypyrazine (36a) as a yellow solid (24 g, 79.4% yield). 1H NMR (400 MHz, CDCl3): δ 7.44 (s, 1H).

References

[1] Patent: WO2010/16005, 2010, A1. Location in patent: Page/Page column 144

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