5,6-Dihydroxypyrazine-2-carboxylic acid

Base Information

• Chemical Name: 5,6-Dihydroxypyrazine-2-carboxylic acid
• CAS No.: 77168-80-0
• Molecular Formula: C₅H₄N₂O₄
• Molecular Weight: 156.098
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID00504553
• Nikkaji Number: J2.613.725J
• Wikidata: Q72505509
• Mol file: 77168-80-0.mol

Synonyms:5,6-Dihydroxypyrazine-2-carboxylic acid;77168-80-0;5,6-dioxo-1,4-dihydropyrazine-2-carboxylic acid;5,6-Dioxo-1,4,5,6-tetrahydropyrazine-2-carboxylic acid;DTXSID00504553;AKOS016012671;5,6-Dihydroxypyrazine-2-carboxylicacid;DS-5443;5,6-Dihydroxy-2-Pyrazinecarboxylic Acid;CS-0109434;O11326

Chemical Property of 5,6-Dihydroxypyrazine-2-carboxylic acid

Chemical Property:

• Melting Point: >300℃
• PSA: 103.02000
• LogP: -1.23860
• Storage Temp.: 2-8°C
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 156.01710661
• Heavy Atom Count: 11
• Complexity: 268

Purity/Quality:

97% ^*data from raw suppliers

5,6-Dihydroxypyrazine-2-carboxylicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(NC(=O)C(=O)N1)C(=O)O

Technology Process of 5,6-Dihydroxypyrazine-2-carboxylic acid

There total 9 articles about 5,6-Dihydroxypyrazine-2-carboxylic acid 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: 10.0%

methyl 5-chloro-2-pyrazinecarboxylate 1-oxide (77168-78-6) → 5,6-dihydroxy-2-pyrazinecarboxylic acid (77168-80-0)

Guidance literature:

With sodium hydroxide; In water; at 70 - 80 ℃; for 5h;

DOI:10.1248/cpb.28.3057

Reference yield:

4,5-dihydro-5-oxo-2-pyrazinecarboxamide (13924-96-4) → 5,6-dihydroxy-2-pyrazinecarboxylic acid (77168-80-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 77 percent / 10percent NaOH / H₂O / 3 h / Heating

2: 64 percent / SOCl₂ / 2 h / Heating

3: 68 percent / POCl₃, DMF / 2 h / Heating

4: 6 percent / MCPBA / 1,2-dichloro-ethane / 39 h / 65 °C

5: 10 percent / NaOH / H₂O / 5 h / 70 - 80 °C

With sodium hydroxide; thionyl chloride; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid; trichlorophosphate; In water; 1,2-dichloro-ethane;

DOI:10.1248/cpb.28.3057

Reference yield:

4,5-dihydro-5-oxo-2-pyrazinecarboxylic acid (34604-60-9) → 5,6-dihydroxy-2-pyrazinecarboxylic acid (77168-80-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 64 percent / SOCl₂ / 2 h / Heating

2: 68 percent / POCl₃, DMF / 2 h / Heating

3: 6 percent / MCPBA / 1,2-dichloro-ethane / 39 h / 65 °C

4: 10 percent / NaOH / H₂O / 5 h / 70 - 80 °C

With sodium hydroxide; thionyl chloride; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid; trichlorophosphate; In water; 1,2-dichloro-ethane;

DOI:10.1248/cpb.28.3057

upstream raw materials:

5-chloro-2-pyrazinecarboxylic acid 1-oxide

methyl 5-chloro-2-pyrazinecarboxylate 1-oxide

4,5-dihydro-5-oxo-2-pyrazinecarboxamide

4,5-dihydro-5-oxo-2-pyrazinecarboxylic acid