2-Amino-5-bromopyrazine Chemical Properties

Melting point:

113-117 °C (lit.)

Boiling point:

274.2±35.0 °C(Predicted)

Density 

1.844±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Ethanol, Ethyl Acetate, Methanol

form 

Brown Needles

pka

1.66±0.10(Predicted)

color 

Light yellow to Brown

InChI

InChI=1S/C4H4BrN3/c5-3-1-8-4(6)2-7-3/h1-2H,(H2,6,8)

InChIKey

KRRTXVSBTPCDOS-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

59489-71-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/38-43-44-36/37/38-20/21/22

Safety Statements 

26-37/39-45-36/37/39-22-36/

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

2-Amino-5-bromopyrazine Usage And Synthesis

Chemical Properties

Brown Needles

Uses

Used without prior protection of the amino group in a palladium-catalyzed cross-coupling with pyridylboronic acids leading to pyrazinylpyridines.

Synthesis

Example 1A Synthesis of 5-bromo-2-pyrazinamine: 2-Aminopyrazine (15.0 g, 157 mmol) was dissolved in dichloromethane (900 mL), N-bromosuccinimide (28.2 g, 159 mmol) was added, and the reaction was stirred for 3.5 hours at room temperature. After completion of the reaction, the reaction mixture was filtered through diatomaceous earth (Celite?). The filtrate was treated with silica gel (300 g) and subsequently concentrated under reduced pressure. The resulting crude product was purified by fast column chromatography with 30% ethyl acetate/hexane as eluent to give 22.09 g (81.5% yield) of the target compound 5-bromo-2-pyrazinamine. Mass spectrum (APCI(+)) m/z: 174 ([M + H]+); 1H NMR (300 MHz, CDCl3) δ: 8.09 (d, J = 1.4 Hz, 1H), 7.77 (d, J = 1.7 Hz, 1H), 4.30-4.78 (br s, 2H).

References

[1] Heterocycles, 2012, vol. 86, # 2, p. 1323 - 1339
[2] Patent: US2004/259885, 2004, A1. Location in patent: Page 9; 10
[3] Patent: US2004/34038, 2004, A1. Location in patent: Page/Page column 10
[4] Patent: WO2011/7314, 2011, A1. Location in patent: Page/Page column 27
[5] Patent: WO2009/44162, 2009, A1. Location in patent: Page/Page column 169

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