2,6-Dihydroxy-4-methyl-3-pyridinecarbonitrile

Base Information

• Chemical Name: 2,6-Dihydroxy-4-methyl-3-pyridinecarbonitrile
• CAS No.: 5444-02-0
• Deprecated CAS: 40401-47-6
• Molecular Formula: C7H6N2O2
• Molecular Weight: 150.137
• Hs Code.: 2933399090
• European Community (EC) Number: 226-639-7,922-665-4
• NSC Number: 19883
• DSSTox Substance ID: DTXSID2063890
• Nikkaji Number: J28.006B
• Wikidata: Q72458070
• Pharos Ligand ID: KZRL8JCLKKL9
• ChEMBL ID: CHEMBL3086510
• Mol file: 5444-02-0.mol

Synonyms:3-cyano-6-hydroxy-4-methyl-2-pyridone

Chemical Property of 2,6-Dihydroxy-4-methyl-3-pyridinecarbonitrile

Chemical Property:

• Vapor Pressure: 0.116mmHg at 25°C
• Melting Point: 315 °C (dec.)(lit.)
• Refractive Index: 1.491
• Boiling Point: 323 °C at 760 mmHg
• PKA: 3.59±0.58(Predicted)
• Flash Point: 149.1 °C
• PSA: 77.14000
• Density: 1.38 g/cm³
• LogP: 0.67288
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 150.042927438
• Heavy Atom Count: 11
• Complexity: 317

Purity/Quality:

99% ^*data from raw suppliers

3-Cyano-2,6-dihydroxy-4-methylpyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC(=O)NC(=C1C#N)O
• Uses: 3-Cyano-2,6-dihydroxy-4-methylpyridine is a synthetic human uridine phosphorylase-1 inhibitor, reduces HepG2 cell proliferation through cell cycle arrest and senescenceis and is used in the synthesis of disperse dyes. Also used in the synthesis of mGluR5 non-competitive antagonists.

Technology Process of 2,6-Dihydroxy-4-methyl-3-pyridinecarbonitrile

There total 25 articles about 2,6-Dihydroxy-4-methyl-3-pyridinecarbonitrile 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: 95.0%

ethyl acetoacetate (141-97-9) + cyanoacetic acid amide (107-91-5) → 2,6-dihydroxy-3-cyano-4-methylpyrimidine (5444-02-0)

Guidance literature:

With potassium hydroxide; In methanol; at 65 ℃; for 8h;

DOI:10.3987/COM-89-S17

Reference yield: 90.0%

2,6-dihydroxy-3-cyano-4-methylpyridine piperidine salt (105143-58-6) → 2,6-dihydroxy-3-cyano-4-methylpyrimidine (5444-02-0)

Guidance literature:

With hydrogenchloride; In water;

Reference yield: 61.0%

ethyl acetoacetate (141-97-9) + cyanoacetic acid amide (107-91-5) → 3-cyano-4-methyl-6-hydroxypyrid-2-one (5444-02-0)

Guidance literature:

With sodium hydroxide; In methanol; water; for 8h; Reflux;

DOI:10.2298/JSC180703092T

upstream raw materials:

piperidine

ethanol

ethyl acetoacetate

cyanoacetic acid amide

Downstream raw materials:

4-methyl-2,6-dihydroxypyridine

2,6-Dihydroxy-4-methyl-5-(p-tolylamino-methyl)-nicotinonitrile

2,6-Dihydroxy-4-methyl-5-(o-tolylamino-methyl)-nicotinonitrile

3-cyano-4-methylpyridine

Refernces

Synthesis, solvatochromism, and biological activity of novel azo dyes bearing 2-pyridone and benzimidazole moieties

10.3906/kim-1711-97

The study focuses on the synthesis, solvatochromism, and biological activity of novel azo dyes that incorporate 2-pyridone and benzimidazole moieties. The azo dyes were synthesized through the diazotization of 4-(1H-benzo[d]imidazol-2-yl)aniline and subsequent coupling with substituted 3-cyano-2-pyridones. The dyes were characterized using UV-Vis, FT-IR, and NMR spectroscopy, as well as elemental analysis. The study explored the solvatochromism of the dyes across various solvents and investigated their tautomeric forms. Biological tests, including MTT assays, revealed that the dyes exhibit good biocompatibility and antiproliferative activity against tumor cell lines MDA-MB-231 and HCT-116, suggesting potential applications in cancer treatment.