4-Chloro-3-fluoropicolinic acid

Base Information

• Chemical Name: 4-Chloro-3-fluoropicolinic acid
• CAS No.: 860296-21-5
• Molecular Formula: C₆H₃ClFNO₂
• Molecular Weight: 175.547
• Hs Code.: 2933399990
• European Community (EC) Number: 830-152-0
• DSSTox Substance ID: DTXSID001264310
• Mol file: 860296-21-5.mol

Synonyms:4-CHLORO-3-FLUOROPICOLINIC ACID;860296-21-5;4-CHLORO-3-FLUOROPYRIDINE-2-CARBOXYLIC ACID;SCHEMBL15060252;DTXSID001264310;MFCD16249576;4-CHLORO-3-FLUOROPICOLINICACID;AKOS022184868;AB70765;AS-54459;4-Chloro-3-fluoro-2-pyridinecarboxylic acid;EN300-125737;S10232;F8889-3340;Z1255421510

Chemical Property of 4-Chloro-3-fluoropicolinic acid

Chemical Property:

• Melting Point: 122-123 °C (decomp)(Solv: water (7732-18-5))
• Boiling Point: 286.8±35.0 °C(Predicted)
• PKA: 2.34±0.10(Predicted)
• Density: 1.576±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 1.4
• 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:

99% ^*data from raw suppliers

4-chloro-3-fluoropyridine-2-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN=C(C(=C1Cl)F)C(=O)O

Technology Process of 4-Chloro-3-fluoropicolinic acid

There total 3 articles about 4-Chloro-3-fluoropicolinic 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: 71.0%

4-chloro-3-fluoro-pyridine (2546-56-7) + carbon dioxide (124-38-9,18923-20-1) → 4-chloro-3-fluoropyridine-2-carboxylic acid (860296-21-5)

Guidance literature:

4-chloro-3-fluoro-pyridine; With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; In tetrahydrofuran; hexane; at -75 ℃; for 0.166667h;

carbon dioxide; In tetrahydrofuran; hexane;

DOI:10.1002/ejoc.200400895

Reference yield:

3-Fluoropyridine (372-47-4) → 4-chloro-3-fluoropyridine-2-carboxylic acid (860296-21-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA / tetrahydrofuran; hexane / 2 h / -75 °C

1.2: 57 percent / 1,1,2-trichloro-2,2,1-trifluoroethane / tetrahydrofuran; hexane

2.1: BuLi; 2,2,6,6-tetramethylpiperidine / tetrahydrofuran; hexane / 0.17 h / -75 °C

2.2: 71 percent / tetrahydrofuran; hexane

With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; lithium diisopropyl amide; In tetrahydrofuran; hexane;

DOI:10.1002/ejoc.200400895

Reference yield:

4-chloro-3-fluoropyridine hydrochloride (119229-74-2) → 4-chloro-3-fluoropyridine-2-carboxylic acid (860296-21-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide / water / pH 14

2.1: n-butyllithium; 2,2,6,6-tetramethyl-piperidine; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C

2.2: 2 h / -78 - 20 °C

With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sodium hydroxide; In tetrahydrofuran; diethyl ether; hexane; water;

upstream raw materials:

4-chloro-3-fluoro-pyridine

carbon dioxide

3-Fluoropyridine

4-chloro-3-fluoropyridine hydrochloride

Downstream raw materials:

3-fluoro(pyridin-2-yl)carboxylic acid

Refernces

• 1、 Marzi, Elena,Bobbio, Carla,Cottet, Fabrice,Schlosser, Manfred. "Converting core compounds into building blocks: The concept of regiochemically exhaustive functionalization". . p. 2116 - 2123. Retrieved 2007/10/03.