6-Hydroxy-5-nitronicotinonitrile

Base Information

• Chemical Name: 6-Hydroxy-5-nitronicotinonitrile
• CAS No.: 320405-84-3
• Molecular Formula: C6H3N3O3
• Molecular Weight: 165.10632
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID00594292
• Nikkaji Number: J2.600.493D
• Mol file: 320405-84-3.mol

Synonyms:6-HYDROXY-5-NITRONICOTINONITRILE;320405-84-3;5-Nitro-6-oxo-1,6-dihydropyridine-3-carbonitrile;5-nitro-6-oxo-1H-pyridine-3-carbonitrile;SCHEMBL7185719;DTXSID00594292;SSYCVCKERZMXLP-UHFFFAOYSA-N;5-cyano-2-hydroxy-3-nitropyridine;VMA40584;MFCD11504985;AKOS006325881;SB54153;6-hydroxy-5-nitropyridine-3-carbonitrile;BS-23407;CS-0082188;D74441;A875731

Chemical Property of 6-Hydroxy-5-nitronicotinonitrile

Chemical Property:

• PSA: 102.73000
• LogP: 1.09028
• Storage Temp.: 2-8°C
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 165.01744097
• Heavy Atom Count: 12
• Complexity: 352

Purity/Quality:

NLT 98% ^*data from raw suppliers

6-Hydroxy-5-nitronicotinonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=C(C(=O)NC=C1C#N)[N+](=O)[O-]

Technology Process of 6-Hydroxy-5-nitronicotinonitrile

There total 3 articles about 6-Hydroxy-5-nitronicotinonitrile 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: 75.0%

5-nitro-6-oxo-1,6-dihydro-3-pyridinecarboxamide (320405-83-2) → 6-hydroxy-5-nitropyridine-3-carbonitrile (320405-84-3)

Guidance literature:

With trichlorophosphate; at 0 - 50 ℃; for 1h;

Reference yield: 67.0%

6-hydroxy-3-pyridinecarbonitrile (94805-52-4,95891-30-8) → 6-hydroxy-5-nitropyridine-3-carbonitrile (320405-84-3)

Guidance literature:

With nitric acid; at 0 - 70 ℃; for 7h; Inert atmosphere;

DOI:10.1016/j.tet.2013.12.026

Reference yield:

6-hydroxy-5-nitronicotinic acid (6635-31-0) → 6-hydroxy-5-nitropyridine-3-carbonitrile (320405-84-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 2 h / 60 °C

1.2: 0.33 h / 60 °C

2.1: trichlorophosphate / 1 h / 0 - 50 °C

With 1,1'-carbonyldiimidazole; trichlorophosphate; In N,N-dimethyl-formamide;

upstream raw materials:

5-nitro-6-oxo-1,6-dihydro-3-pyridinecarboxamide

6-hydroxy-3-pyridinecarbonitrile

6-hydroxy-5-nitronicotinic acid

Downstream raw materials:

6-chloro-5-nitro-3-pyridinecarbonitrile

Refernces

• 1、 Sapegin, Alexander V.,Kalinin, Stanislav A.,Smirnov, Alexey V.,Dorogov, Mikhail V.,Krasavin, Mikhail. "New tetracyclic 1,4-oxazepines constructed via practically simple tandem condensation strategy from readily available synthons". . p. 1077 - 1083. Retrieved 2014/01/23.