Methyl 6-chloro-4-(trifluoromethyl)nicotinate

Base Information

• Chemical Name: Methyl 6-chloro-4-(trifluoromethyl)nicotinate
• CAS No.: 261635-79-4
• Molecular Formula: C₈H₅ClF₃NO₂
• Molecular Weight: 239.581
• Hs Code.: 2933399090
• European Community (EC) Number: 671-232-3
• DSSTox Substance ID: DTXSID10379532
• Wikidata: Q82169382
• Mol file: 261635-79-4.mol

Synonyms:METHYL 6-CHLORO-4-(TRIFLUOROMETHYL)NICOTINATE;261635-79-4;methyl 6-chloro-4-(trifluoromethyl)pyridine-3-carboxylate;MFCD01941315;3-Pyridinecarboxylic acid, 6-chloro-4-(trifluoromethyl)-, methyl ester;SCHEMBL473983;DTXSID10379532;BBL102191;STL555990;AKOS015851235;PS-11258;methyl 6-chloro-4-trifluoromethylnicotinate;CS-0046073;FT-0648513;Methyl6-chloro-4-(trifluoromethyl)nicotinate;methyl-6-chloro-4-(trifluoromethyl)nicotinate;C74354;EN300-133309;methyl 6-chloro-4-(trifluoromethyl)-nicotinate;methyl-6-chloro-4-(trifluoromethyl)-nicotinate;6-chloro-4-trifluoromethyl-nicotinic acid methyl ester;methyl 6-chloro-4-trifluoromethylpyridin-3-ylcarboxylate;Z1509716046;Methyl 6-chloro-4-(trifluoromethyl)nicotinate, AldrichCPR

Chemical Property of Methyl 6-chloro-4-(trifluoromethyl)nicotinate

Chemical Property:

• Vapor Pressure: 0.0127mmHg at 25°C
• Refractive Index: 1.466
• Boiling Point: 259.7 °C at 760 mmHg
• Flash Point: 110.9 °C
• PSA: 39.19000
• Density: 1.443 g/cm³
• LogP: 2.54040
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 238.9960906
• Heavy Atom Count: 15
• Complexity: 247

Purity/Quality:

98%min ^*data from raw suppliers

Methyl 6-chloro-4-(trifluoromethyl)nicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Methyl 6-chloro-4-(trifluoromethyl)nicotinate

There total 4 articles about Methyl 6-chloro-4-(trifluoromethyl)nicotinate 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: 80.4%

dimethyl sulfate (77-78-1) + 6-chloro-4-(trifluoromethyl)pyridine-3-carboxylic acid (261635-77-2) → methyl 6-chloro-4-(trifluoromethyl)pyridine-3-carboxylate (261635-79-4)

Guidance literature:

With potassium carbonate; In acetone; at 0 - 20 ℃; for 16h;

Reference yield:

5-bromo-2-chloro-4-(trifluoromethyl)pyridine (823221-93-8) → methyl 6-chloro-4-(trifluoromethyl)pyridine-3-carboxylate (261635-79-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: butyl magnesium bromide; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

1.2: 16 h / 20 °C

2.1: potassium carbonate / acetone / 2 h / 0 - 20 °C

With n-butyllithium; butyl magnesium bromide; potassium carbonate; In tetrahydrofuran; hexane; acetone;

Reference yield:

5-bromo-4-iodo-2-chloropyridine (401892-47-5) → methyl 6-chloro-4-(trifluoromethyl)pyridine-3-carboxylate (261635-79-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: copper(l) iodide / N,N-dimethyl-formamide / 6 h / 100 °C / Inert atmosphere

2.1: butyl magnesium bromide; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

2.2: 16 h / 20 °C

3.1: potassium carbonate / acetone / 2 h / 0 - 20 °C

With copper(l) iodide; n-butyllithium; butyl magnesium bromide; potassium carbonate; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; acetone;

upstream raw materials:

dimethyl sulfate

6-chloro-4-(trifluoromethyl)pyridine-3-carboxylic acid

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

5-bromo-4-iodo-2-chloropyridine

Downstream raw materials:

C₁₄H₁₀F₄N₂O₂

C₁₄H₁₀BrF₃N₂O₂

C₁₅H₁₂ClF₃N₂O₂

C₁₅H₁₂ClF₃N₂O₃

Refernces

• 1、 -. "INHIBITORS OF WDR5 PROTEIN-PROTEIN BINDING". Paragraph 00320; 00326-00327. . Retrieved 2017/09/15.