CAS
10124-78-4 Purity
96%
10124-78-4 Purity
96%
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2-Aminopyrazine
CAS
1012570-55-6
Catalog Number
ACM1012570556
Category
Other Products
Molecular Weight
95.1
Molecular Formula
C4H5N3
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Specification
Synonyms
2-Aminopyrazine, pyrazin-2-amine, Aminopyrazine, 5049-61-6, Pyrazinamine, 2-Pyrazinamine, pyrazin-2-ylamine, pyrazine-2-ylamine, CHEMBL1834089, AC-907/25014024, zlchem 313, Pyrazine, 2-amino-, AMINO PYRAZINE, 3-AMINOPYRAZINE, 2-Piperazinamine(9CI), AC1L2VVP, SureCN29032, ACMC-209kn1, SureCN432791, AC1Q1I8Q
IUPAC Name
pyrazin-2-amine
Canonical SMILES
C1=CN=C(C=N1)N
InChI Key
XFTQRUTUGRCSGO-UHFFFAOYSA-N
EC Number
225-748-7
Exact Mass
95.04830
H-Bond Acceptor
3
H-Bond Donor
1
Cyclocondensation Reaction for the Synthesis of a Polycyclic Scaffold Using 2-Aminopyrazine under Aqueous Hydrochloric Acid Conditions
Valdo A. K., et al. Journal of Molecular Structure, 2021, 1242, 130723.
A concise and efficient cyclocondensation reaction of 2-aminopyrazine was demonstrated under mild aqueous hydrochloric acid conditions, yielding a structurally complex ionic polycyclic product. The reaction involves the condensation of the diazine ring system in 2-aminopyrazine, a typically stable aromatic compound, with hydrochloric acid in water at ambient temperature. Remarkably, this transformation proceeds without the need for elevated temperatures or pressures, deviating from the harsh conditions usually required for aromatization-disruptive cyclizations. The resulting product, a dihydrochloride salt monohydrate featuring four fused six-membered rings, was isolated and crystallographically characterized. Single-crystal X-ray diffraction confirmed the unexpected loss of aromaticity and the formation of a polycyclic framework. Structural integrity and assignment were further validated through DFT optimization at the B3LYP/6-311G level, while Mogul geometry analysis reinforced conformational fidelity. This method showcases a rare example of electrophilic cyclocondensation in aqueous media, highlighting the unique reactivity of 2-aminopyrazine under protic acidic conditions.
Crystal Engineering of Copper(II) Complexes Using 2-Aminopyrazine: Synthesis of Cu(hfac)₂(2-apz)₂ and Cu₃(hfac)₆(2-apz)₂
Li L, et al. Inorganica Chimica Acta, 2009, 362(10), 3845-3852.
The coordination behavior of 2-aminopyrazine (2-apz) was explored in the synthesis of discrete and multinuclear copper(II) complexes using hexafluoroacetylacetonate copper(II) hydrate [Cu(hfac)₂·xH₂O] as the metal source. In a representative experiment, a dichloromethane solution of Cu(hfac)₂·xH₂O (0.513 g, 1.0 mmol) was added dropwise under stirring to a solution of 2-apz (0.095 g, 1.0 mmol) in CH₂Cl₂ (14.0 mL). The immediate formation of a green precipitate indicated complexation, which was removed via filtration. The resulting dark blue filtrate was left partially covered at ambient conditions, allowing for slow evaporation over four days, leading to the isolation of two crystalline products. X-ray diffraction identified these as the mononuclear complex Cu(hfac)₂(2-apz)₂ and the trinuclear Cu₃(hfac)₆(2-apz)₂, each displaying distinct coordination environments. The 2-apz ligand acted as both monodentate and bridging bidentate donor, promoting the formation of mixed nuclearities. Structural data indicated enhanced Cu-N bond interaction due to the amino functionality. This case exemplifies how 2-aminopyrazine facilitates structural diversity in coordination compounds, supporting its utility in molecular design for magnetic and material studies.
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