5-(Trifluoromethyl)nicotinic acid

Base Information

• Chemical Name: 5-(Trifluoromethyl)nicotinic acid
• CAS No.: 131747-40-5
• Molecular Formula: C7H4F3NO2
• Molecular Weight: 191.109
• Hs Code.: 2933399090
• European Community (EC) Number: 689-333-6
• DSSTox Substance ID: DTXSID80450428
• Nikkaji Number: J2.008.070A
• Wikidata: Q72512130
• ChEMBL ID: CHEMBL3617323
• Mol file: 131747-40-5.mol

Synonyms:131747-40-5;5-(trifluoromethyl)nicotinic acid;5-(trifluoromethyl)pyridine-3-carboxylic Acid;5-trifluoromethyl nicotinic acid;3-PYRIDINECARBOXYLIC ACID, 5-(TRIFLUOROMETHYL)-;5-(trifluoromethyl)-3-pyridinecarboxylic acid;5-Trifluoromethylnicotinic acid;CHEMBL3617323;5-(TRIFLUOROMETHY)PYRIDINE-3-CARBOXYLIC ACID;MFCD07774128;5-trifluoromethyl-nicotinic acid;5-(trifluoromethyl)pyridin-3-carboxylic acid;SCHEMBL185622;DTXSID80450428;BCP05789;CS-D0146;BBL101019;BDBM50122015;STL554813;AKOS005063763;AB42318;AC-1901;DS-0510;FS-2593;BL001598;SY016842;5-trifluoromethyl-3-pyridinecarboxylic acid;5-Trifluoromethylpyridine-3-carboxylic acid;AM20050761;FT-0649975;EN300-96103;5-(Trifluoromethyl)pyridine-3-carboxylic acid, 95%;A1-00193;W-205368;Z1201624167

Chemical Property of 5-(Trifluoromethyl)nicotinic acid

Chemical Property:

• Vapor Pressure: 0.002mmHg at 25°C
• Melting Point: 184-189℃
• Refractive Index: 1.475
• Boiling Point: 277.494 °C at 760 mmHg
• PKA: 3.04±0.10(Predicted)
• Flash Point: 121.624 °C
• PSA: 50.19000
• Density: 1.485 g/cm³
• LogP: 1.79860
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 191.01941286
• Heavy Atom Count: 13
• Complexity: 204

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-(Trifluoromethyl)nicotinicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 5-(Trifluoromethyl)nicotinic acid

There total 7 articles about 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: 87.0%

2-chloro-5-(trifluoromethyl)pyridine-3-carboxylic acid (505084-59-3) → 5-(trifluoromethyl)pyridine-3-carboxylic acid (131747-40-5)

Guidance literature:

With ammonium formate; 10% palladium on active carbon; In methanol; at 25 ℃; for 0.25h;

DOI:10.1002/ejoc.200390215

Reference yield: 33.0%

carbon dioxide (124-38-9,18923-20-1) + 3-bromo-5-(trifluoromethyl)pyridine (436799-33-6) → 5-(trifluoromethyl)pyridine-3-carboxylic acid (131747-40-5)

Guidance literature:

With tri-n-butyllithium magnesate complex; In toluene; at -75 ℃; for 0.25h;

DOI:10.1002/ejoc.200390215

Reference yield:

2-chloro-5-trifluoromethylpyridine (52334-81-3) → 5-(trifluoromethyl)pyridine-3-carboxylic acid (131747-40-5)

Guidance literature:

Multi-step reaction with 4 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

4.1: 87 percent / ammonium formate / palladium (10 percent on charcoal) / methanol / 0.25 h / 25 °C

With piperidine; n-butyllithium; ammonium formate; diisopropylamine; lithium bromide; lithium N,N-diisopropylcarbamate; 10% palladium on active carbon; In tetrahydrofuran; methanol; hexane;

DOI:10.1002/ejoc.200390215

upstream raw materials:

trimethylaluminum

3-chloro-5-(trifluoromethyl)pyridine

carbon dioxide

3-bromo-5-(trifluoromethyl)pyridine

Downstream raw materials:

3-(bromomethyl)-5-(trifluoromethyl)pyridine

5-{(2-methyl-5-[(5-(trifluoromethyl)pyridine-3-carbonyl)amino]benzyl)amino}-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid methyl ester

Refernces

• 1、 Wang, Junhua,Wang, Honglin,Ren, Hongmin,Dong, Lihua. "Selective decarboxylation: A facile synthesis of 3-pyridinecarboxylic acid derivative". experimental part. p. 4139 - 4142. Retrieved 2009/12/24.
• 2、 Ashimori,Ono,Uchida,Ohtaki,Fukaya,Watanabe,Yokoyama. "Novel 1,4-dihydropyridine calcium antagonists. I. Synthesis and hypotensive activity of 4-(substituted pyridyl)-1,4-dihydropyridine derivatives". . p. 2446 - 2458. Retrieved 2007/10/02.