3-(3-Methoxypyridin-2-yl)benzaldehyde

Base Information

• Chemical Name: 3-(3-Methoxypyridin-2-yl)benzaldehyde
• CAS No.: 868992-04-5
• Molecular Formula: C12H8 Br N O
• Molecular Weight: 262.1
• DSSTox Substance ID: DTXSID20698786
• Wikidata: Q82629249
• Mol file: 868992-04-5.mol

Synonyms:3-(3-methoxypyridin-2-yl)benzaldehyde;Benzaldehyde,3-(6-bromo-2-pyridinyl)-;1699266-88-0;DTXSID20698786;A1-17518

Chemical Property of 3-(3-Methoxypyridin-2-yl)benzaldehyde

Chemical Property:

• PSA: 39.19000
• LogP: 2.56970
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 213.078978594
• Heavy Atom Count: 16
• Complexity: 232

Purity/Quality:

99% ^*data from raw suppliers

3-(6-Bromo-pyridin-2-yl)benzaldehyde 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(N=CC=C1)C2=CC=CC(=C2)C=O

Technology Process of 3-(3-Methoxypyridin-2-yl)benzaldehyde

There total 1 articles about 3-(3-Methoxypyridin-2-yl)benzaldehyde 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: 56.0%

2,6-Dibromopyridine (626-05-1) + 3-Formylphenylboronic acid (87199-16-4) → 2-bromo-6-(3-formylphenyl)pyridine (868992-04-5)

Guidance literature:

With sodium carbonate; triphenylphosphine; palladium diacetate; In 1,2-dimethoxyethane; water; for 22h; Heating;

DOI:10.1016/j.tet.2005.08.018

Reference yield: 47.0%

2-bromo-6-(3-formylphenyl)pyridine (868992-04-5) → 6,6'-bis(3-formylphenyl)-2,2'-bipyridine (868992-05-6)

Guidance literature:

With triphenylphosphine; nickel dichloride; zinc; In N,N-dimethyl-formamide; at 60 ℃; for 23h;

DOI:10.1016/j.tet.2005.08.018

Reference yield:

2-bromo-6-(3-formylphenyl)pyridine (868992-04-5) → acetic acid 3,5-diacetoxy-2-acetoxymethyl-6-[3-(4-{3-[6'-(3-{4-[3-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propyl]-phenoxymethyl}-phenyl)-[2,2']bipyridinyl-6-yl]-benzyloxy}-phenyl)-propoxy]-tetrahydro-pyran-4-yl ester (868992-09-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 47 percent / nickel dichloride hexahydrate; triphenylphosphine; zinc / dimethylformamide / 23 h / 60 °C

2: 96 percent / NaBH₄ / ethanol / 3 h / 20 °C

3: 82 percent / PBr₃ / CH₂Cl₂ / 16.5 h / 0 - 20 °C

4: 30 percent / cesium carbonate / dimethylformamide; acetonitrile / 18 h / 20 °C

With sodium tetrahydroborate; phosphorus tribromide; caesium carbonate; triphenylphosphine; nickel dichloride; zinc; In ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tet.2005.08.018

upstream raw materials:

2,6-Dibromopyridine

3-Formylphenylboronic acid

Downstream raw materials:

6,6'-bis(3-formylphenyl)-2,2'-bipyridine

6,6'-bis(3-hydroxymethylphenyl)-2,2'-bipyridine

6,6'-bis(3-bromomethylphenyl)-2,2'-bipyridine

acetic acid 3,5-diacetoxy-2-acetoxymethyl-6-[3-(4-{3-[6'-(3-{4-[3-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propyl]-phenoxymethyl}-phenyl)-[2,2']bipyridinyl-6-yl]-benzyloxy}-phenyl)-propoxy]-tetrahydro-pyran-4-yl ester