| Identification | More | [Name]
2-Amino-5-bromopyrazine | [CAS]
59489-71-3 | [Synonyms]
2-AMINO-5-BROMOPYRAZINE
5-BROMO-2-PYRAZINAMINE
5-BROMOPYRAZIN-2-AMINE
5-BROMO-PYRAZIN-2-YLAMINE
5-BROMOPYRAZINAMINE
BUTTPARK 29\02-91
2-aimo-5-bromopyrazine
5-Bromo-2-aminopyrazine
2-AMINO-5-BROMOPYRAZINE: TECH.
2-Bromo-5-aminopyrazine | [EINECS(EC#)]
626-202-4 | [Molecular Formula]
C4H4BrN3 | [MDL Number]
MFCD00235015 | [Molecular Weight]
174 | [MOL File]
59489-71-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Brown Needles | [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 Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/38:Irritating to eyes and skin .
R43:May cause sensitization by skin contact.
R44:Risk of explosion if heated under confinement.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [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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