5-BROMO-6-CHLOROPYRAZIN-2-AMINE Chemical Properties

Boiling point:

311.8±37.0 °C(Predicted)

Density 

1.960

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMF: 25mg/mL,DMF:PBS (pH 7.2) (1:5): 0.16mg/mL,DMSO: 15mg/mL,Ethanol: 20mg/mL

form 

A crystalline solid

pka

-0.67±0.10(Predicted)

Appearance

brown solid

InChI

InChI=1S/C4H3BrClN3/c5-3-4(6)9-2(7)1-8-3/h1H,(H2,7,9)

InChIKey

CRVPQFAORCSDMH-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

T

Risk Statements 

25-37/38-41

Safety Statements 

26-39-45

RIDADR 

2811

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

2933998090

5-BROMO-6-CHLOROPYRAZIN-2-AMINE Usage And Synthesis

Uses

5-Bromo-6-chloropyrazin-2-amine (Compound 110) is an organic compound used as an intermediate in the synthesis of various bioactive molecules. 5-Bromo-6-chloropyrazin-2-amine is promising for research of bacterial infections, such as tuberculosis[1].

Synthesis

General procedure for the synthesis of 2-amino-5-bromo-6-chloropyrazine from 2-amino-6-chloropyrazine: 6-chloropyrazin-2-amine (10.4 g, 80 mmol) was dissolved in methanol (300 mL), and N-bromosuccinimide (15.6 g, 88 mmol) was added slowly with stirring at room temperature. The reaction mixture was continued to stir for 60 min and then concentrated under reduced pressure to remove the solvent. Water was added to the concentrate and extracted with ethyl acetate (3 x 100 mL). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with the eluent being a solvent mixture of hashane and ethyl acetate (3:1, v/v) to afford the target compound 2-amino-5-bromo-6-chloropyrazine (12.0 g, 72% yield).1H NMR (500 MHz, CDCl3) δ 7.69 (s, 1H), 4.73 (s, 2H).

References

[1] Szychowski J, et al. Discovery of an orally bioavailable and selective PKMYT1 inhibitor, RP-6306[J]. Journal of medicinal chemistry, 2022, 65(15): 10251-10284.

5-BROMO-6-CHLOROPYRAZIN-2-AMINE(173253-42-4)Related Product Information

• 2-[1-(5-BROMO-6-CHLOROPYRAZIN-2-YL)PIPERIDIN-4-YL]-1H-ISOINDOLE-1,3(2H)-DIONE
• TERT-BUTYL [1-(5-BROMO-6-CHLOROPYRAZIN-2-YL)PIPERIDIN-4-YL]CARBAMATE
• 5-BROMO-6-CHLOROPYRAZIN-2-AMINE
• TERT-BUTYL 4-(5-BROMO-6-CHLOROPYRAZIN-2-YL)PIPERAZINE-1-CARBOXYLATE
• 5-BROMO-6-CHLORO-3-METHOXYPYRAZIN-2-AMINE
• 3,5-DIBROMO-6-CHLOROPYRAZIN-2-AMINE