3-Cyano-2,6-dihydroxy-5-fluoropyridine

Base Information

• Chemical Name: 3-Cyano-2,6-dihydroxy-5-fluoropyridine
• CAS No.: 113237-18-6
• Molecular Formula: C6H3FN2O2
• Molecular Weight: 154.1
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID30356148
• Wikidata: Q72466662
• Mol file: 113237-18-6.mol

Synonyms:113237-18-6;3-cyano-2,6-dihydroxy-5-fluoropyridine;5-fluoro-2,6-dihydroxynicotinonitrile;2,6-Dihydroxy-5-fluoro-3-cyanopyridine;5-fluoro-6-hydroxy-2-oxo-1H-pyridine-3-carbonitrile;5-Fluoro-6-hydroxy-2-oxo-1,2-dihydropyridine-3-carbonitrile;2,6-Dihydroxy-5-fluoro-3-cyano-pyridine;5-fluoro-2,6-dihydroxypyridine-3-carbonitrile;SCHEMBL3686316;DTXSID30356148;JWNUZZLUDDUXPO-UHFFFAOYSA-N;MFCD03001419;AKOS006277485;SB52840;2,6-dihydroxy-3-cyano-5-fluoropyridine;AC-11751;TS-02050;2,6-Dihydroxy -5-fluoro-3-cyanopyridine;CS-0059189;FT-0620386;D86495;AN-668/25093007;W-200852

Chemical Property of 3-Cyano-2,6-dihydroxy-5-fluoropyridine

Chemical Property:

• Vapor Pressure: 0.0283mmHg at 25°C
• Melting Point: 235-245 °C
• Refractive Index: 1.578
• Boiling Point: 217.5 °C at 760 mmHg
• PKA: 1.43±0.58(Predicted)
• Flash Point: 85.4 °C
• PSA: 77.14000
• Density: 1.58 g/cm³
• LogP: 0.50358
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 154.01785550
• Heavy Atom Count: 11
• Complexity: 321

Purity/Quality:

99% ^*data from raw suppliers

3-Cyano-2,6-dihydroxy-5-fluoropyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=O)NC(=C1F)O)C#N

Technology Process of 3-Cyano-2,6-dihydroxy-5-fluoropyridine

There total 2 articles about 3-Cyano-2,6-dihydroxy-5-fluoropyridine 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:

sodium 3-ethoxy-2-fluoro-3-oxoprop-1-en-1-olate (1652-39-7) + cyanoacetic acid amide (107-91-5) → 5-fluoro-2,6-dihydroxynicotinonitrile (113237-18-6)

Guidance literature:

With sodium ethanolate; In ethanol; for 0.25h; Yield given; Heating;

DOI:10.1248/cpb.35.2280

Reference yield:

→ 5-fluoro-2,6-dihydroxynicotinonitrile (113237-18-6)

Guidance literature:

Reference yield: 48.0%

ethyl potassium malonate (6148-64-7) + 5-fluoro-2,6-dihydroxynicotinonitrile (113237-18-6) → ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate (96568-04-6)

Guidance literature:

5-fluoro-2,6-dihydroxynicotinonitrile; With phosphorus pentachloride; trichlorophosphate; Heating / reflux;

ethyl potassium malonate; With zinc(II) chloride; In 1,2-dichloro-ethane; Heating / reflux;

With hydrogenchloride; water; In 1,2-dichloro-ethane; at 90 ℃; for 4h; Product distribution / selectivity;

upstream raw materials:

sodium 3-ethoxy-2-fluoro-3-oxoprop-1-en-1-olate

cyanoacetic acid amide

Downstream raw materials:

2,6-dichloro-5-fluoro-pyridine-3-carbonitrile

ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate

Refernces

• 1、 Miyamoto,Egawa,Matsumoto. "Pyridonecarboxylic acids as antibacterial agents. VIII. An alternative synthesis of enoxacin via fluoronicotinic acid derivatives". . p. 2280 - 2285. Retrieved 2007/10/02.