3,5-Dichloro-6-fluoropicolinic acid

Base Information

• Chemical Name: 3,5-Dichloro-6-fluoropicolinic acid
• CAS No.: 406676-39-9
• Molecular Formula: C₆H₂Cl₂FNO₂
• Molecular Weight: 209.992
• DSSTox Substance ID: DTXSID10455421
• Nikkaji Number: J1.662.532I
• Wikidata: Q82277397
• Mol file: 406676-39-9.mol

Synonyms:3,5-Dichloro-6-fluoropicolinic acid;406676-39-9;3,5-DICHLORO-6-FLUOROPYRIDINE-2-CARBOXYLIC ACID;SCHEMBL22400088;DTXSID10455421;3,5-Dichloro-6-fluoropicolinicacid;AKOS016012924;3,5-Dichloro-6-fluoro-2-pyridinecarboxylic acid

Chemical Property of 3,5-Dichloro-6-fluoropicolinic acid

Chemical Property:

• PSA: 50.19000
• LogP: 2.22570
• Storage Temp.: 2-8°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 208.9446619
• Heavy Atom Count: 12
• Complexity: 192

Purity/Quality:

95+% ^*data from raw suppliers

3,5-Dichloro-6-fluoropicolinicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 3,5-Dichloro-6-fluoropicolinic acid

There total 4 articles about 3,5-Dichloro-6-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: 51.0%

carbon dioxide (124-38-9,18923-20-1) + 3,5-dichloro-2-fluoro-6-iodopyridine (406676-35-5) → 3,5-dichloro-2-fluoro-6-pyridinecarboxylic acid (406676-39-9)

Guidance literature:

3,5-dichloro-2-fluoro-6-iodopyridine; With isopropylmagnesium chloride; In tetrahydrofuran; at -75 ℃; for 0.75h;

carbon dioxide; at -75 ℃; Further stages.;

DOI:10.1002/1099-0690(200112)2001:23<4533::AID-EJOC4533>3.0.CO;2-1

Reference yield:

2,3,5-trichloropyridine (16063-70-0) → 3,5-dichloro-2-fluoro-6-pyridinecarboxylic acid (406676-39-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 86 percent / KF / tetrahydrothiophene 1,1-dioxide / 20 h / 180 °C

2.1: 73 percent / lithium diisopropylamide; iodine / tetrahydrofuran; hexane / -75 °C

3.1: 56 percent / lithium 2,2,6,6-tetramethylpiperidine; H₂O / tetrahydrofuran; methanol / -100 - -75 °C

4.1: isopropylmagnesium chloride / tetrahydrofuran / 0.75 h / -75 °C

4.2: 51 percent / -75 °C

With potassium fluoride; 2,2,6,6-tetramethylpiperidinyl-lithium; water; iodine; isopropylmagnesium chloride; lithium diisopropyl amide; In tetrahydrofuran; sulfolane; methanol; hexane;

DOI:10.1002/1099-0690(200112)2001:23<4533::AID-EJOC4533>3.0.CO;2-1

Reference yield:

2-Fluoro-3,5-dichloropyridine (823-56-3) → 3,5-dichloro-2-fluoro-6-pyridinecarboxylic acid (406676-39-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 73 percent / lithium diisopropylamide; iodine / tetrahydrofuran; hexane / -75 °C

2.1: 56 percent / lithium 2,2,6,6-tetramethylpiperidine; H₂O / tetrahydrofuran; methanol / -100 - -75 °C

3.1: isopropylmagnesium chloride / tetrahydrofuran / 0.75 h / -75 °C

3.2: 51 percent / -75 °C

With 2,2,6,6-tetramethylpiperidinyl-lithium; water; iodine; isopropylmagnesium chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane;

DOI:10.1002/1099-0690(200112)2001:23<4533::AID-EJOC4533>3.0.CO;2-1

upstream raw materials:

carbon dioxide

3,5-dichloro-2-fluoro-6-iodopyridine

2,3,5-trichloropyridine

2-Fluoro-3,5-dichloropyridine

Refernces