6-Chloro-4-(trifluoromethyl)nicotinic acid

Base Information

• Chemical Name: 6-Chloro-4-(trifluoromethyl)nicotinic acid
• CAS No.: 261635-77-2
• Molecular Formula: C₇H₃ClF₃NO₂
• Molecular Weight: 225.555
• Hs Code.: 2933399090
• European Community (EC) Number: 672-886-2
• DSSTox Substance ID: DTXSID30382624
• Wikidata: Q82173980
• Mol file: 261635-77-2.mol

Synonyms:6-Chloro-4-(trifluoromethyl)nicotinic acid;261635-77-2;6-chloro-4-(trifluoromethyl)pyridine-3-carboxylic Acid;6-CHLORO-4-(TRIFLUOROMETHYL)NICOTINICACID;MFCD06800446;3-Pyridinecarboxylic acid, 6-chloro-4-(trifluoromethyl)-;SCHEMBL1536029;DTXSID30382624;BULUOEXUXOKCIG-UHFFFAOYSA-N;AMY19043;AKOS015851212;AB29974;DS-5007;6-chloro-4-trifluoromethyinicotinic acid;6-chloro-4-trifluoromethyl-nicotinic acid;SY022647;FT-0677424;EN300-112839;O11574;A818225;6-Chloro-4-(trifluoromethyl)nicotinic acid, AldrichCPR;Z1269209675

Chemical Property of 6-Chloro-4-(trifluoromethyl)nicotinic acid

Chemical Property:

• Vapor Pressure: 0.000266mmHg at 25°C
• Melting Point: 95-105°C
• Boiling Point: 309.9°Cat760mmHg
• PKA: 2.29±0.36(Predicted)
• Flash Point: 141.3°C
• PSA: 50.19000
• Density: 1.603g/cm³
• LogP: 2.45200
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• 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:

98%min ^*data from raw suppliers

6-Chloro-4-trifluoromethylnicotinicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=CN=C1Cl)C(=O)O)C(F)(F)F
• Uses: 6-Chloro-4-trifluoromethylnicotinic Acid is a building blocked used in organic synthesis such as the preparation of N-aryl heteroarylcarboxamides as inhibitors of WDR5 protein-protein binding.

Technology Process of 6-Chloro-4-(trifluoromethyl)nicotinic acid

There total 3 articles about 6-Chloro-4-(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: 77.0%

carbon dioxide (124-38-9,18923-20-1) + 5-bromo-2-chloro-4-(trifluoromethyl)pyridine (823221-93-8) → 6-chloro-4-(trifluoromethyl)pyridine-3-carboxylic acid (261635-77-2)

Guidance literature:

5-bromo-2-chloro-4-(trifluoromethyl)pyridine; With n-butyllithium; butyl magnesium bromide; In tetrahydrofuran; hexane; at -75 ℃;

carbon dioxide; In tetrahydrofuran; hexane;

DOI:10.1016/j.tet.2004.09.106

Reference yield:

5-bromo-2-chloropyridine (53939-30-3) → 6-chloro-4-(trifluoromethyl)pyridine-3-carboxylic acid (261635-77-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.75 h / -75 °C

1.2: 66 percent / iodine / tetrahydrofuran; hexane

2.1: 64 percent / potassium fluoride; cuprous iodide; N-methylpyrrolidinone / 20 h / 50 °C

3.1: butylmagnesium chloride; butyllithium / hexane; tetrahydrofuran / -75 °C

3.2: 77 percent / tetrahydrofuran; hexane

With 1-methyl-pyrrolidin-2-one; potassium fluoride; copper(l) iodide; n-butyllithium; butyl magnesium bromide; lithium diisopropyl amide; In tetrahydrofuran; hexane;

DOI:10.1016/j.tet.2004.09.106

Reference yield:

5-bromo-4-iodo-2-chloropyridine (401892-47-5) → 6-chloro-4-(trifluoromethyl)pyridine-3-carboxylic acid (261635-77-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 64 percent / potassium fluoride; cuprous iodide; N-methylpyrrolidinone / 20 h / 50 °C

2.1: butylmagnesium chloride; butyllithium / hexane; tetrahydrofuran / -75 °C

2.2: 77 percent / tetrahydrofuran; hexane

With 1-methyl-pyrrolidin-2-one; potassium fluoride; copper(l) iodide; n-butyllithium; butyl magnesium bromide; In tetrahydrofuran; hexane;

DOI:10.1016/j.tet.2004.09.106

upstream raw materials:

carbon dioxide

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

5-bromo-2-chloropyridine

5-bromo-4-iodo-2-chloropyridine

Refernces

• 1、 -. "INHIBITORS OF WDR5 PROTEIN-PROTEIN BINDING". Paragraph 00264. . Retrieved 2017/09/15.