5-bromopyrazin-2-amine

• ChemBase ID: 64316
• Molecular Formular: C4H4BrN3
• Molecular Mass: 173.99866
• Monoisotopic Mass: 172.95885914
• SMILES: n1c(cnc(c1)Br)N
• Canonical SMILES: Nc1ncc(nc1)Br
• InChI: InChI=1S/C4H4BrN3/c5-3-1-8-4(6)2-7-3/h1-2H,(H2,6,8)
• InChIKey: KRRTXVSBTPCDOS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-bromopyrazin-2-amine
• IUPAC Traditional name: 5-bromopyrazin-2-amine
• Synonyms: 5-bromo-2-pyrazinamine; 5-Bromo-2-pyrazinamine; 5-Bromopyrazin-2-ylamine; 5-Bromopyrazinamine; 5-Bromo-2-aminopyrazine; 5-bromopyrazin-2-amine; 2-Amino-5-bromopyrazine; 5-Bromopyrazin-2-amine; 2-Amino-5-bromopyrazine; 2-氨基-5-溴吡嗪

Database IDs

• CAS Number: 59489-71-3
• MDL Number: MFCD00235015
• PubChem SID: 162030055; 24882771
• PubChem CID: 599539

CALCULATED PROPERTIES

• Acid pKa: 19.90652
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.2776853
• LogD (pH = 7.4): 0.2777069
• Log P: 0.2777072
• Molar Refractivity: 35.2231 cm^3
• Polarizability: 12.739177 Å^3
• Polar Surface Area: 51.8 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol; Ethyl Acetate; Methanol
• Apperance: Brown Needles
• Melting Point: 106 - 108°C; 113-117 °C(lit.); 113-117°C; 113-117°C
• Hydrophobicity(logP): 0.31

Safety Information

• Storage Warning: Harmful/Irritant; IRRITANT
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38; 22-36/38-43
• Safety Statements: 26-36/37; 26-37/39
• TSCA Listed: false; 否
• GHS Pictograms: GHS05; GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335; H302-H315-H317-H318
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: 95%; 97%; 98%; TECH
• Empirical Formula (Hill Notation): C4H4BrN3

DETAILS

Sigma Aldrich - 636320

Application
Used without prior protection of the amino group in a palladium-catalyzed cross-coupling with pyridylboronic acids leading to pyrazinylpyridines.1
Packaging
1 g in glass bottle

REFERENCES

• Shi, Z., et al.: J. Med. Chem., 51, 3684 (2008)
• Onda, K., et al.: Bioorg. Med. Chem., 16, 5452 (2008)