2-Chloro-6-methoxynicotinaldehyde

Base Information

• Chemical Name: 2-Chloro-6-methoxynicotinaldehyde
• CAS No.: 95652-80-5
• Molecular Formula: C7H6ClNO2
• Molecular Weight: 171.583
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID70538921
• Wikidata: Q82414496
• Mol file: 95652-80-5.mol

Synonyms:2-Chloro-6-methoxynicotinaldehyde;95652-80-5;2-CHLORO-6-METHOXYPYRIDINE-3-CARBALDEHYDE;2-chloro-6-methoxy-pyridine-3-carbaldehyde;SCHEMBL15228338;DTXSID70538921;QXHZQUBXMXEKMX-UHFFFAOYSA-N;VDA65280;MFCD10697549;AKOS006303650;AB59889;CS-W007212;DS-16650;W17184;A849347;2-CHLORO-6-METHOXY-3-PYRIDINECARBOXALDEHYDE;2-CHLORO-6-METHOXYPYRIDINE-3-CARBOXALDEHYDE;J-508952

Chemical Property of 2-Chloro-6-methoxynicotinaldehyde

Chemical Property:

• Vapor Pressure: 0.004mmHg at 25°C
• Boiling Point: 277.661oC at 760 mmHg
• Flash Point: 121.725oC
• PSA: 39.19000
• Density: 1.317g/cm3
• LogP: 1.55610
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 171.0087061
• Heavy Atom Count: 11
• Complexity: 142

Purity/Quality:

98%min ^*data from raw suppliers

2-Chloro-6-methoxynicotinaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=NC(=C(C=C1)C=O)Cl

Technology Process of 2-Chloro-6-methoxynicotinaldehyde

There total 3 articles about 2-Chloro-6-methoxynicotinaldehyde 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: 59.0%

methanol (67-56-1) + 2-chloro-3-(trichloromethyl)-pyridine (72648-12-5) → 2,6-dimethoxypyridine-3-carboxaldehyde (58819-72-0) + 2-chloro-6-methoxy-3-pyridine-carboxaldehyde (95652-80-5) + 2-chloro-3-(dimethoxymethyl)-6-methoxypyridine (95652-79-2)

Guidance literature:

With sodium;

DOI:10.1016/S0040-4039(01)91414-5

Reference yield: 35.0%

sodium methylate (124-41-4) + 2-chloro-3-(trichloromethyl)-pyridine (72648-12-5) → 2,6-dimethoxypyridine-3-carboxaldehyde (58819-72-0) + 2-chloro-6-methoxy-3-pyridine-carboxaldehyde (95652-80-5)

Guidance literature:

In tetrahydrofuran; for 15h; Heating;

Reference yield:

sodium methylate (124-41-4) + 2,6-dichloro-3-pyridinecarbonitrile (40381-90-6) → 2-chloro-6-methoxy-3-pyridine-carboxaldehyde (95652-80-5) + 6-chloro-2-methoxy-3-pyridinecarboxaldehyde (95652-81-6)

Guidance literature:

With methanol; diisobutylaluminum hydride; Multistep reaction. Title compound not separated from byproducts; 1.) methanol, room temperature, 1 h, 2.) toluene, room temperature, 1 h;

upstream raw materials:

methanol

2-chloro-3-(trichloromethyl)-pyridine

sodium methylate

2,6-dichloro-3-pyridinecarbonitrile

Downstream raw materials:

tert-butyl 3-((2S,3S)-5-(tert-butoxy)-3-(2-((4-methoxybenzyl)oxy)ethyl)-1-nitro-4,5-dioxopentan-2-yl)-6-methoxypicolinate

1-benzyl 2-(tert-butyl) (2R,3S,4S)-4-(2-(tert-butoxycarbonyl)-6-methoxypyridin-3-yl)-3-(2-((4-methoxybenzyl)oxy)ethyl)pyrrolidine-1,2-carboxylate

1-benzyl 2-(tert-butyl) (2S,3S,4S)-4-(2-(tert-butoxycarbonyl)-6-methoxypyridin-3-yl)-3-(2-((4-methoxybenzyl)oxy)ethyl)pyrrolidine-1,2-carboxylate

1-benzyl 2-(tert-butyl) (2S,3S,4S)-4-(2-(tert-butoxycarbonyl)-6-methoxypyridin-3-yl)-3-(2-hydroxyethyl)pyrrolidine-1,2-dicarboxylate

Refernces

• 1、 Dainter, Ronald S.,Suschitzky, Hans,Wakefield, Basil J.,Hughes, Nigel,Nelson, Anthony J.. "ABNORMAL NUCLEOPHILIC SUBSTITUTION OF 3-TRICHLOROMETHYLPYRIDINES BY METHOXIDE". . p. 5693 - 5696. Retrieved 2007/10/02.