5-Chloro-4-(trifluoromethyl)picolinic acid

Base Information

• Chemical Name: 5-Chloro-4-(trifluoromethyl)picolinic acid
• CAS No.: 796090-31-8
• Molecular Formula: C₇H₃ClF₃NO₂
• Molecular Weight: 225.555
• Hs Code.: 2933399990
• European Community (EC) Number: 937-991-2
• DSSTox Substance ID: DTXSID90458359
• Nikkaji Number: J2.126.892E
• Wikidata: Q82281584
• Mol file: 796090-31-8.mol

Synonyms:796090-31-8;5-Chloro-4-(trifluoromethyl)picolinic acid;5-chloro-4-(trifluoromethyl)pyridine-2-carboxylic Acid;5-CHLORO-4-(TRIFLUOROMETHYL)-2-PYRIDINECARBOXYLIC ACID;SCHEMBL16793887;DTXSID90458359;ZUECDOBROYTMSJ-UHFFFAOYSA-N;MFCD18256834;AKOS015991328;AB74813;CG-0714;5-Chloro-4-(trifluoromethyl)picolinicacid;EN300-154586;Y10135;A864834;4-(Trifluoromethyl)-5-chloropyridine-2-carboxylic acid;5-CHLORO-4-TRIFLUOROMETHYL-PYRIDINE-2-CARBOXYLIC ACID

Chemical Property of 5-Chloro-4-(trifluoromethyl)picolinic acid

Chemical Property:

• Boiling Point: 322.4±42.0 °C(Predicted)
• PKA: 2.98±0.10(Predicted)
• PSA: 50.19000
• Density: 1.603±0.06 g/cm3(Predicted)
• 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:

97% ^*data from raw suppliers

5-Chloro-4-(trifluoromethyl)-2-pyridinecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=CN=C1C(=O)O)Cl)C(F)(F)F
• Uses: 5-Chloro-4-(trifluoromethyl)-2-pyridinecarboxylic Acid, used as model substrates for regioexhaustive functionalization.

Technology Process of 5-Chloro-4-(trifluoromethyl)picolinic acid

There total 8 articles about 5-Chloro-4-(trifluoromethyl)picolinic 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:

ethyl 5-chloro-4-(trifluoromethyl)picolinate → 5-chloro-4-(trifluoromethyl)picolinic acid (796090-31-8)

Guidance literature:

at 20 ℃; Alkaline conditions; Reflux;

Reference yield:

5-chloro-4-trifluoromethyl-6-trimethylsilanyl-pyridine-2-carboxylic acid (1026187-48-3) → 5-chloro-4-(trifluoromethyl)picolinic acid (796090-31-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.0166667h; Heating;

DOI:10.1002/ejoc.200400066

Reference yield:

3-chloro-4-iodopyridine (77332-79-7) → 5-chloro-4-(trifluoromethyl)picolinic acid (796090-31-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: potassium fluoride; cuprous iodide; N-methylpyrrolidinone / 0.5 h / 50 °C

1.2: 69 percent / 20 h / 50 °C

2.1: 74 percent / lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -75 °C

3.1: 2,2,6,6-tetramethylpiperidine; butyllithium / tetrahydrofuran; hexane / 2 h / -75 °C

3.2: 85 percent / iodine / tetrahydrofuran; hexane / 0.25 h / -75 °C

4.1: 2,2,6,6-tetramethylpiperidine; butyllithium / diethyl ether; hexane / 1 h / -75 °C

4.2: 62 percent / aq. hydrochloric acid / diethyl ether; hexane

5.1: butyllithium / toluene; hexane / 0.25 h / -75 °C

5.2: toluene; hexane; tetrahydrofuran

5.3: aq. hydrochloric acid / toluene; hexane; tetrahydrofuran / 25 °C

6.1: 1.68 g / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 0.02 h / Heating

With 2,2,6,6-tetramethyl-piperidine; 1-methyl-pyrrolidin-2-one; potassium fluoride; copper(l) iodide; n-butyllithium; tetrabutyl ammonium fluoride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; toluene;

DOI:10.1002/ejoc.200400066

upstream raw materials:

5-chloro-4-trifluoromethyl-6-trimethylsilanyl-pyridine-2-carboxylic acid

3-chloro-4-iodopyridine

4-(trifluoromethyl)nicotinyl chloride

3-chloro-4-(trifluoromethyl)-2-(trimethylsilyl)pyridine