3-Chloro-5-fluoroisonicotinic acid

Base Information

• Chemical Name: 3-Chloro-5-fluoroisonicotinic acid
• CAS No.: 514798-03-9
• Molecular Formula: C₆H₃ClFNO₂
• Molecular Weight: 175.547
• European Community (EC) Number: 849-885-2
• DSSTox Substance ID: DTXSID40450020
• Nikkaji Number: J1.861.138D
• Wikidata: Q82269586
• Mol file: 514798-03-9.mol

Synonyms:3-Chloro-5-fluoroisonicotinic acid;514798-03-9;3-chloro-5-fluoropyridine-4-carboxylic acid;SCHEMBL16135687;DTXSID40450020;MFCD13185823;AKOS016008265;AB66801;AS-10492;5-Chloro-3-fluoropyridine-4-carboxylic acid;CS-0183288;EN300-122812;A905272;3-CHLORO-5-FLUORO-4-PYRIDINECARBOXYLIC ACID

Chemical Property of 3-Chloro-5-fluoroisonicotinic acid

Chemical Property:

• Boiling Point: 348.2±37.0 °C(Predicted)
• PKA: 0.99±0.25(Predicted)
• PSA: 50.19000
• Density: 1.576±0.06 g/cm3(Predicted)
• LogP: 1.57230
• Storage Temp.: 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 174.9836342
• Heavy Atom Count: 11
• Complexity: 167

Purity/Quality:

95% ^*data from raw suppliers

3-Chloro-5-fluoroisonicotinicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=C(C=N1)Cl)C(=O)O)F
• Uses: 3-Chloro-5-fluoroisonicotinic Acid is used in preparation of Oxodihydropyridopyrimidine derivatives for use as eIF4E inhibitors.

Technology Process of 3-Chloro-5-fluoroisonicotinic acid

There total 5 articles about 3-Chloro-5-fluoroisonicotinic 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: 85.0%

carbon dioxide (124-38-9,18923-20-1) + 3-chloro-5-fluoro-pyridine (514797-99-0) → 3-chloro-5-fluoro-4-pyridinecarboxylic acid (514798-03-9)

Guidance literature:

3-chloro-5-fluoro-pyridine; With n-butyllithium; In tetrahydrofuran; hexane; at -75 ℃; for 2h;

carbon dioxide; In tetrahydrofuran; hexane;

DOI:10.1002/1099-0690(200212)2002:24<4174::AID-EJOC4174>3.0.CO;2-6

Reference yield:

5-chloro-2,3-difluoropyridine (89402-43-7) → 3-chloro-5-fluoro-4-pyridinecarboxylic acid (514798-03-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 91 percent / aq. sodium hydroxide / 20 h / 75 °C

2.1: 97 percent / phosphoryl tribromide / dimethylformamide / 2 h / 130 °C

3.1: 92 percent / aq. sodium hydroxide; zinc powder / 6 h / 25 °C

4.1: butyllithium / tetrahydrofuran; hexane / 2 h / -75 °C

4.2: 85 percent / tetrahydrofuran; hexane

With sodium hydroxide; n-butyllithium; zinc; phosphorus(V) oxybromide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1002/1099-0690(200212)2002:24<4174::AID-EJOC4174>3.0.CO;2-6

Reference yield:

2-bromo-5-chloro-3-fluoro-pyridine (514797-97-8) → 3-chloro-5-fluoro-4-pyridinecarboxylic acid (514798-03-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 92 percent / aq. sodium hydroxide; zinc powder / 6 h / 25 °C

2.1: butyllithium / tetrahydrofuran; hexane / 2 h / -75 °C

2.2: 85 percent / tetrahydrofuran; hexane

With sodium hydroxide; n-butyllithium; zinc; In tetrahydrofuran; hexane;

DOI:10.1002/1099-0690(200212)2002:24<4174::AID-EJOC4174>3.0.CO;2-6

upstream raw materials:

carbon dioxide

3-chloro-5-fluoro-pyridine

5-chloro-2,3-difluoropyridine

2-bromo-5-chloro-3-fluoro-pyridine

Refernces

• 1、 Schlosser, Manfred,Bobbio, Carla. "Creating structural manifolds from a common precursor: Basicity gradient-driven isomerization of halopyridines". . p. 4174 - 4180. Retrieved 2007/10/03.