5-Nitro-2-sulfanylidene-1H-pyridine-3-carboxylic acid

Base Information

• Chemical Name: 5-Nitro-2-sulfanylidene-1H-pyridine-3-carboxylic acid
• CAS No.: 156896-47-8
• Molecular Formula: C₆H₄N₂O₄S
• Molecular Weight: 200.175
• DSSTox Substance ID: DTXSID60566177
• Wikidata: Q82451664
• Mol file: 156896-47-8.mol

Synonyms:156896-47-8;5-NITRO-2-SULFANYLIDENE-1H-PYRIDINE-3-CARBOXYLIC ACID;3-Pyridinecarboxylicacid,1,2-dihydro-5-nitro-2-thioxo-(9CI);SCHEMBL9100948;DTXSID60566177;5-Nitro-2-sulfanylidene-1,2-dihydropyridine-3-carboxylic acid

Chemical Property of 5-Nitro-2-sulfanylidene-1H-pyridine-3-carboxylic acid

Chemical Property:

• PSA: 134.81000
• LogP: 1.49990
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 199.98917779
• Heavy Atom Count: 13
• Complexity: 352

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=S)NC=C1[N+](=O)[O-])C(=O)O

Technology Process of 5-Nitro-2-sulfanylidene-1H-pyridine-3-carboxylic acid

There total 6 articles about 5-Nitro-2-sulfanylidene-1H-pyridine-3-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: 80.0%

ethyl 1,2-dihydro-5-nitro-2-thioxo-3-pyridinecarboxylate (156896-57-0) → 1,2-dihydro-5-nitro-2-thioxo-3-pyridinecarboxylic acid (156896-47-8)

Guidance literature:

With potassium hydroxide; In ethanol; for 2h; Ambient temperature;

DOI:10.3987/COM-93-6556

Reference yield:

1,2-dihydro-5-nitro-2-oxo-3-pyridinecarboxylic acid → 1,2-dihydro-5-nitro-2-thioxo-3-pyridinecarboxylic acid (156896-47-8)

Guidance literature:

Multi-step reaction with 5 steps

1: SOCl₂ / toluene / 2 h / Heating

2: 3 h / Heating

3: 85 percent / POCl₃, DMF / chlorobenzene / 4 h / Heating

4: 87 percent / NaSH*H₂O / aq. ethanol / 1 h / Heating

5: 80 percent / KOH / aq. ethanol / 2 h / Ambient temperature

With potassium hydroxide; sodium hydrogensulfide; thionyl chloride; N,N-dimethyl-formamide; trichlorophosphate; In ethanol; chlorobenzene; toluene;

DOI:10.3987/COM-93-6556

Reference yield:

ethyl 2-chloro-5-nitro-3-pyridinecarboxylate (151322-83-7) → 1,2-dihydro-5-nitro-2-thioxo-3-pyridinecarboxylic acid (156896-47-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / NaSH*H₂O / aq. ethanol / 1 h / Heating

2: 80 percent / KOH / aq. ethanol / 2 h / Ambient temperature

With potassium hydroxide; sodium hydrogensulfide; In ethanol;

DOI:10.3987/COM-93-6556

upstream raw materials:

bis(2-chloro-5-nitro-3-pyridinecarboxylic) anhydride

ethyl 1,2-dihydro-5-nitro-2-thioxo-3-pyridinecarboxylate

ethyl 2-chloro-5-nitro-3-pyridinecarboxylate

ethyl 1,2-dihydro-5-nitro-2-oxo-3-pyridinecarboxylate