| Identification | Back Directory | [Name]
5-BROMO-6-CHLOROPYRAZIN-2-AMINE | [CAS]
173253-42-4 | [Synonyms]
132788
2-Amine-5-bromo-6-chloropyrazin
5-BROMO-6-CHLOROPYRAZIN-2-AMINE
5-Amino-2-bromo-3-chloropyrazine
2-AMINO-5-BROMO-6-CHLOROPYRAZINE
2-Pyrazinamine, 5-bromo-6-chloro-
5-Bromo-6-chloro-pyrazin-2-ylamine
5-BROMO-6-CHLOROPYRAZIN-2-AMINE ISO 9001：2015 REACH
2-Bromo-3-chloropyrazin-5-amine, 5-Bromo-6-chloropyrazin-2-amine, 3-Bromo-2-chloropyrazin-6-amine | [Molecular Formula]
C4H3BrClN3 | [MDL Number]
MFCD09909642 | [MOL File]
173253-42-4.mol | [Molecular Weight]
208.44 |
| Chemical Properties | Back Directory | [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) | [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 |
| Hazard Information | Back Directory | [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. |
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