2-Hydroxypyrazine

Base Information

• Chemical Name: 2-Hydroxypyrazine
• CAS No.: 6270-63-9
• Molecular Formula: C4H4 N2 O
• Molecular Weight: 96.0886
• Hs Code.: 2933990090
• European Community (EC) Number: 228-455-2
• NSC Number: 36081
• UNII: N5VLE8C2MU
• DSSTox Substance ID: DTXSID10211781
• Nikkaji Number: J92.509H
• Wikidata: Q72481526
• Mol file: 6270-63-9.mol

Synonyms:1,2-dihydropyrazin-2-one

Chemical Property of 2-Hydroxypyrazine

Chemical Property:

• Melting Point: 185-186 ºC
• PKA: 11.69±0.20(Predicted)
• PSA: 46.01000
• Density: 1.28g/cm3
• LogP: 0.18220
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 96.032362755
• Heavy Atom Count: 7
• Complexity: 137

Purity/Quality:

97% ^*data from raw suppliers

2-Hydroxypyrazine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN=CC(=O)N1
• Uses: 2-Hydroxypyrazine also used in the synthesis of potential antioxidants. Is also used in the preparation of antibacterial agents as 2-substituted pyrazine derivatives.

Technology Process of 2-Hydroxypyrazine

There total 24 articles about 2-Hydroxypyrazine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

pyrazin-2-ylboronic acid (762263-64-9) → pyrazin-2-ol (6270-63-9)

Guidance literature:

With hydrazine hydrate; caesium carbonate; In water; at 80 ℃; for 12h;

Reference yield: 53.0%

2-Aminopyrazine (5049-61-6) → pyrazin-2(1H)-one (6270-63-9)

Guidance literature:

With sulfuric acid; sodium nitrite; at 0 - 40 ℃; for 1h;

DOI:10.1016/j.bmc.2019.01.007

Reference yield: 53.0%

1-benzyloxy-2(1H)-pyrazinone (149280-95-5) → pyrazin-2(1H)-one (6270-63-9)

Guidance literature:

In benzene; for 1.5h; Irradiation;

DOI:10.3987/com-96-7392

upstream raw materials:

2-chloropyrazin

2-Aminopyrazine

Glyoxal

glycinamide hydrochloride

Downstream raw materials:

3-phenyl-2(1H)-pyrazinone

3,6-diphenylpyrazin-2(1H)-one

2-chloropyrazin

2-bromopyrazine

Refernces

3-Substituted pyrazinone nucleosidesA new family of D4T analogues

10.1080/15257770903169999

The study investigates the synthesis and antiviral properties of a new family of nucleoside analogues derived from pyrazinone, aiming to explore their potential as anti-HIV agents. The researchers synthesized compounds 5a, 5b, and 5c, which are analogues of the nucleoside 2′,3′-didehydro-2′,3′-dideoxythymidine (d4T). The synthesis process involved several steps, including selective deprotection of hydroxyl groups, formation of bisxanthate intermediates, and radical reactions to introduce double bonds. The compounds were characterized using techniques like 1H NMR and infrared spectroscopy. The study found that these compounds did not exhibit antiviral activity against HIV-1 or cytotoxic effects in tested cell lines. The chemicals involved include pyrazinone nucleosides, methanolic ammonia for deprotection, carbon disulfide, sodium hydride, and methyl iodide for bisxanthate formation, and tributylphosphine-borane for the radical reaction. The roles of these chemicals are crucial in the structural modification of the nucleoside analogues to enhance their lipophilicity and potential membrane permeability, although the final compounds did not show the desired antiviral activity.