5-Fluoronicotinic acid

Base Information

• Chemical Name: 5-Fluoronicotinic acid
• CAS No.: 402-66-4
• Molecular Formula: C6H4FNO2
• Molecular Weight: 141.102
• Hs Code.: 29339900
• European Community (EC) Number: 674-996-6
• UNII: 9C94XTS5CX
• DSSTox Substance ID: DTXSID60193200
• Nikkaji Number: J3.152.555A
• Wikidata: Q72475089
• ChEMBL ID: CHEMBL397783
• Mol file: 402-66-4.mol

Synonyms:5-fluoro-3-pyridinecarboxylic acid;5-fluoronicotinic acid

Chemical Property of 5-Fluoronicotinic acid

Chemical Property:

• Vapor Pressure: 0.473mmHg at 25°C
• Melting Point: 193-198℃
• Refractive Index: 1.534
• Boiling Point: 272.2 °C at 760 mmHg
• PKA: 3.13±0.10(Predicted)
• Flash Point: 118.4 °C
• PSA: 50.19000
• Density: 1.419 g/cm³
• LogP: 0.91890
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Soluble in methanol.
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 141.02260653
• Heavy Atom Count: 10
• Complexity: 140

Purity/Quality:

99.9% ^*data from raw suppliers

5-Fluoronicotinic Acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C=NC=C1F)C(=O)O
• Recent ClinicalTrials: Induction CT by Cisplatin, 5FU With or Without Docetaxel in Patients With T3 and T4 Larynx and Hypopharynx Carcinoma
• Uses: 5-Fluoronicotinic acid is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.

Technology Process of 5-Fluoronicotinic acid

There total 2 articles about 5-Fluoronicotinic 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:

2,6-dichloro-5-fluoro-3-pyridinecarboxylic acid (82671-06-5) → 5-fluoropyridine-3-carboxylic acid (402-66-4)

Guidance literature:

With hydrogen; triethylamine; 5% palladium over charcoal; In methanol; at 0 - 20 ℃; for 4h;

Reference yield:

2-amino-3-methyl-5-nitropyridine (18344-51-9) → 5-fluoropyridine-3-carboxylic acid (402-66-4)

Guidance literature:

Multi-step reaction with 5 steps

1: calcium chloride; aqueous sodium nitrite solution; aqueous hydrochloric acid / Erhitzen des Reaktionsprodukts mit Wasser

2: phosphoryl chloride

3: palladium/charcoal; sodium acetate; acetic acid / Hydrogenation

4: ethyl nitrite / Erwaermen des erhaltenen Diazoniumsalzes mit Petrolaether

5: KMnO₄; H₂O

With hydrogenchloride; potassium permanganate; palladium on activated charcoal; ethyl nitrite; water; sodium acetate; acetic acid; calcium chloride; sodium nitrite; trichlorophosphate;

DOI:10.1021/jo01154a021

Reference yield: 80.0%

5-fluoropyridine-3-carboxylic acid (402-66-4) + C13H12F4N4O2 → C19H14F5N5O3

Guidance literature:

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; at 0 - 20 ℃; for 3h;

DOI:10.1007/s11030-021-10340-1

upstream raw materials:

2-amino-3-methyl-5-nitropyridine

2,6-dichloro-5-fluoro-3-pyridinecarboxylic acid

Downstream raw materials:

5-fluoro-3-pyridinecarbonyl chloride

5-fluoro-6-hydroxy-nicotinic acid

5-fluoro-3-pyridinecarboxylic acid methyl ester

3-fluoro-5-benzyloxycarbonylaminopyridine

Refernces