2-Chloro-5-(trifluoromethyl)nicotinic acid

Base Information

• Chemical Name: 2-Chloro-5-(trifluoromethyl)nicotinic acid
• CAS No.: 505084-59-3
• Molecular Formula: C7H3ClF3NO2
• Molecular Weight: 225.555
• Hs Code.: 2933399090
• European Community (EC) Number: 684-460-3
• DSSTox Substance ID: DTXSID90478375
• Nikkaji Number: J2.126.893C
• Wikidata: Q72460433
• Mol file: 505084-59-3.mol

Synonyms:505084-59-3;2-Chloro-5-(trifluoromethyl)nicotinic acid;2-chloro-5-(trifluoromethyl)pyridine-3-carboxylic acid;2-chloro-5-(trifluoromethyl)-3-pyridinecarboxylic acid;2-chloro-5-trifluoromethylnicotinic acid;2-Chloro-5-trifluoromethyl-nicotinic acid;MFCD08741353;3-PYRIDINECARBOXYLIC ACID, 2-CHLORO-5-(TRIFLUOROMETHYL)-;2-Chloro-5-(trifluoromethyl)nicotinicAcid;SCHEMBL1585179;DTXSID90478375;BCP11617;AKOS005255973;AB48756;CS-W008174;PS-6917;AC-25222;BL003417;SY020525;AM20061266;FT-0649993;FT-0698488;EN300-49455;A828144;J-508801;2-chloro-5-(trifluoromethyl)-3-pyridine carboxylic acid;Z381542710;2-chloranyl-5-(trifluoromethyl)pyridine-3-carboxylic acid;2-Chloro-5-(trifluoromethyl)pyridine-3-carboxylic acid, 97%

Chemical Property of 2-Chloro-5-(trifluoromethyl)nicotinic acid

Chemical Property:

• Melting Point: 281ºC
• Boiling Point: 301.5 °C at 760 mmHg
• PKA: 1.57±0.25(Predicted)
• Flash Point: 136.1 °C
• PSA: 50.19000
• Density: 1.603 g/cm³
• LogP: 2.45200
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 224.9804405
• Heavy Atom Count: 14
• Complexity: 234

Purity/Quality:

99%Min ^*data from raw suppliers

2-Chloro-5-(trifluoromethyl)pyridine-3-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn,T
• Statements: 22-36/37/38-25
• Safety Statements: 22-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=NC(=C1C(=O)O)Cl)C(F)(F)F

Technology Process of 2-Chloro-5-(trifluoromethyl)nicotinic acid

There total 4 articles about 2-Chloro-5-(trifluoromethyl)nicotinic 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: 65.0%

carbon dioxide (124-38-9,18923-20-1) + 2-chloro-3-iodo-5-(trifluoromethyl)pyridine (505084-56-0) → 2-chloro-5-(trifluoromethyl)pyridine-3-carboxylic acid (505084-59-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -75 ℃; for 0.25h;

DOI:10.1002/ejoc.200390215

Reference yield: 37.0%

carbon dioxide (124-38-9,18923-20-1) + 2-chloro-5-trifluoromethylpyridine (52334-81-3) → 2-chloro-5-(trifluoromethyl)pyridine-3-carboxylic acid (505084-59-3) + 2-chloro-5-(trifluoromethyl)pyridine-4-carboxylic acid (505084-58-2) + 2-chloro-5-(trifluoromethyl)pyridine-3,4-dicarboxylic acid

Guidance literature:

2-chloro-5-trifluoromethylpyridine; With n-butyllithium; diisopropylamine; sodium bromide; In tetrahydrofuran; hexane; at -75 ℃; for 2h;

carbon dioxide; In tetrahydrofuran; hexane;

With sodium hydroxide; In tetrahydrofuran; hexane;

DOI:10.1002/ejoc.200400066

Reference yield:

2-chloro-5-trifluoromethylpyridine (52334-81-3) → 2-chloro-5-(trifluoromethyl)pyridine-3-carboxylic acid (505084-59-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium N,N-diisopropylcarbamate; diisopropylamine; lithium bromide / tetrahydrofuran; hexane / 2 h / -75 °C

1.2: 67 percent / iodine / tetrahydrofuran; hexane / 0.75 h / -75 °C

2.1: 46 percent / piperidine; butyllithium / tetrahydrofuran; hexane / 20 h / -75 °C

3.1: 65 percent / butyllithium / hexane; tetrahydrofuran / 0.25 h / -75 °C

With piperidine; n-butyllithium; diisopropylamine; lithium bromide; lithium N,N-diisopropylcarbamate; In tetrahydrofuran; hexane;

DOI:10.1002/ejoc.200390215

upstream raw materials:

carbon dioxide

2-chloro-3-iodo-5-(trifluoromethyl)pyridine

2-chloro-5-trifluoromethylpyridine

2-chloro-4-iodo-5-(trifluoromethyl)pyridine

Downstream raw materials:

methyl 2-chloro-5-(trifluoromethyl)pyridine-3-carboxylate

Refernces

• 1、 Cottet, Fabrice,Marull, Marc,Lefebvre, Olivier,Schlosser, Manfred. "Recommendable routes to trifluoromethyl-substituted pyridine- and quinolinecarboxylic acids". . p. 1559 - 1568. Retrieved 2007/10/03.