Methyl 6-chloro-5-fluoronicotinate

Base Information

• Chemical Name: Methyl 6-chloro-5-fluoronicotinate
• CAS No.: 78686-78-9
• Molecular Formula: C₇H₅ClFNO₂
• Molecular Weight: 189.574
• Hs Code.: 2933399990
• European Community (EC) Number: 811-543-5
• DSSTox Substance ID: DTXSID10506563
• Wikidata: Q82362363
• Mol file: 78686-78-9.mol

Synonyms:78686-78-9;methyl 6-chloro-5-fluoronicotinate;Methyl 6-chloro-5-fluoropyridine-3-carboxylate;SCHEMBL990912;DTXSID10506563;methyl6-chloro-5-fluoronicotinate;KDMTVIVGDHCOAH-UHFFFAOYSA-N;AMY38439;MFCD14698136;AKOS016015633;PS-6731;SB52956;CS-0181862;EN300-7412497;6-chloro-5-fluoropyridine-3-carboxylic acid methyl ester;Z1255459532;3-PYRIDINECARBOXYLIC ACID,6-CHLORO-5-FLUORO-,METHYL ESTER

Chemical Property of Methyl 6-chloro-5-fluoronicotinate

Chemical Property:

• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 188.9992843
• Heavy Atom Count: 12
• Complexity: 179

Purity/Quality:

99% ^*data from raw suppliers

methyl6-chloro-5-fluoropyridine-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC(=C(N=C1)Cl)F

Technology Process of Methyl 6-chloro-5-fluoronicotinate

There total 3 articles about Methyl 6-chloro-5-fluoronicotinate 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: 32.0%

5-bromo-2-chloro-3-fluoro-pyridine (831203-13-5) + methyl chloroformate (79-22-1) → methyl 6-chloro-5-fluoropyridine-3-carboxylate (78686-78-9)

Guidance literature:

5-bromo-2-chloro-3-fluoro-pyridine; With TurboGrignard; In tetrahydrofuran; at 0 - 15 ℃; for 2.5h; Inert atmosphere;

methyl chloroformate; In tetrahydrofuran; at 0 - 15 ℃; for 11.5h; Inert atmosphere;

Reference yield:

6-chloro-5-fluoronicotinic acid (38186-86-6) → methyl 6-chloro-5-fluoropyridine-3-carboxylate (78686-78-9)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / 1 h / Heating

2: benzene / 1 h / Heating

With thionyl chloride; In benzene;

DOI:10.1021/je00025a033

Reference yield:

methanol (67-56-1) + 6-Chloro-5-fluoro-nicotinoyl chloride (78686-85-8) → methyl 6-chloro-5-fluoropyridine-3-carboxylate (78686-78-9)

Guidance literature:

In benzene; for 1h; Yield given; Heating;

DOI:10.1021/je00025a033

upstream raw materials:

methanol

6-Chloro-5-fluoro-nicotinoyl chloride

6-chloro-5-fluoronicotinic acid

5-bromo-2-chloro-3-fluoro-pyridine

Refernces

• 1、 Setliff, Frank L.,Hule, W. Reeves. "Some Methyl 2,5- and 5,6-Dihalonicotinates". . p. 332 - 333. Retrieved 2007/10/02.