3-Chloro-5-methoxyisonicotinic acid

Base Information

• Chemical Name: 3-Chloro-5-methoxyisonicotinic acid
• CAS No.: 214976-36-0
• Molecular Formula: C7H6ClNO3
• Molecular Weight: 187.58044
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID00440700
• Wikidata: Q82257072
• Mol file: 214976-36-0.mol

Synonyms:3-Chloro-5-methoxyisonicotinic acid;214976-36-0;3-chloro-5-methoxypyridine-4-carboxylic acid;3-Chloro-5-methoxyisonicotinicacid;SCHEMBL5201967;DTXSID00440700;MFCD18256978;AKOS016004283;DS-3751

Chemical Property of 3-Chloro-5-methoxyisonicotinic acid

Chemical Property:

• PSA: 59.42000
• LogP: 1.44180
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 187.0036207
• Heavy Atom Count: 12
• Complexity: 176

Purity/Quality:

NLT 98% ^*data from raw suppliers

3-Chloro-5-methoxyisonicotinicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CN=CC(=C1C(=O)O)Cl

Technology Process of 3-Chloro-5-methoxyisonicotinic acid

There total 2 articles about 3-Chloro-5-methoxyisonicotinic 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:

3,5-dichloropyridine (2457-47-8) → 3-chloro-5-methoxyisonicotinic acid (214976-36-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / Na / dimethylformamide / 1.5 h / 70 - 75 °C

2: 1.) LDA / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, from -78 deg C to RT, 2.5 h

With sodium; lithium diisopropyl amide; In N,N-dimethyl-formamide;

DOI:10.1002/jhet.5570350419

Reference yield:

carbon dioxide (124-38-9,18923-20-1) + 5-chloro-3-methoxypyridine (95881-83-7) → 3-chloro-5-methoxyisonicotinic acid (214976-36-0)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, from -78 deg C to RT, 2.5 h;

DOI:10.1002/jhet.5570350419

Reference yield:

3-chloro-5-methoxyisonicotinic acid (214976-36-0) → 3-(5-Chloro-2-fluoro-benzyl)-5-methoxy-isonicotinic acid (214976-39-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / diethyl ether; ethanol

2: 1.) Zn, 2.) bisnickel(II) chloride / 1.) THF, 0 deg C, 3 h, 2.) THF, RT, 3 h

3: 90 percent / aq. NaOH / methanol / 2 h / Heating

With sodium hydroxide; bis(triphenylphosphine)nickel(II) chloride; zinc; In methanol; diethyl ether; ethanol;

DOI:10.1002/jhet.5570350419

upstream raw materials:

carbon dioxide

5-chloro-3-methoxypyridine

3,5-dichloropyridine

Downstream raw materials:

3-(5-Chloro-2-fluoro-benzyl)-5-methoxy-isonicotinic acid

3-(5-Chloro-2-fluoro-benzyl)-5-methoxy-isonicotinic acid methyl ester

C₂₂H₂₆ClN₃O₂

Refernces