2-Methoxy-5-(pyridin-4-yl)benzaldehyde

Base Information

• Chemical Name: 2-Methoxy-5-(pyridin-4-yl)benzaldehyde
• CAS No.: 385802-40-4
• Molecular Formula: C13H11NO2
• Molecular Weight: 213.236
• European Community (EC) Number: 840-109-8
• Mol file: 385802-40-4.mol

Synonyms:2-methoxy-5-(pyridin-4-yl)benzaldehyde;385802-40-4;2-methoxy-5-pyridin-4-ylbenzaldehyde;2-methoxy-5-pyridin-4-yl-benzaldehyde;SCHEMBL3252986;OOTSXFWEFCBQQP-UHFFFAOYSA-N;MFCD12785843;AKOS010309095;2-methoxy-5-(pridin-4-yl)benzaldehyde;CS-0195694;E90763;EN300-152291;Z756099100

Chemical Property of 2-Methoxy-5-(pyridin-4-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: 226

Purity/Quality:

97% ^*data from raw suppliers

2-Methoxy-5-(pyridin-4-yl)benzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-Methoxy-5-(pyridin-4-yl)benzaldehyde

There total 5 articles about 2-Methoxy-5-(pyridin-4-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: 96.0%

4-bromopyridine hydrochloride (19524-06-2) + 3-formyl-4-methoxyphenylboronic acid (121124-97-8) → 2-methoxy-5-(pyridin-4-yl)benzaldehyde (385802-40-4)

Guidance literature:

4-bromopyridine hydrochloride; 3-formyl-4-methoxyphenylboronic acid; With potassium carbonate; bis-triphenylphosphine-palladium(II) chloride; In ethanol; water; at 80 ℃; for 2h; Heating / reflux;

With hydrogenchloride; In ethanol; water; ethyl acetate; at 40 - 50 ℃; for 0.5h; pH=2 - 3;

With sodium hydroxide; In water; for 1h; pH=12 - 13; Product distribution / selectivity;

Reference yield: 95.0%

2-(1,3-dioxolan-2-yl)-4-(4-pyridinyl)anisole (892483-05-5) → 2-methoxy-5-(pyridin-4-yl)benzaldehyde (385802-40-4)

Guidance literature:

With sulfuric acid; In acetone; for 0.166667h; Heating / reflux;

Reference yield: 85.0%

4-pyridylboronic acid (1692-15-5) + 5-bromo-2-methoxybenzaldehyde (25016-01-7) → 2-methoxy-5-(pyridin-4-yl)benzaldehyde (385802-40-4)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; In 1,4-dioxane; at 80 ℃; for 12h; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.6b03438

upstream raw materials:

4-bromopyridin

3-formyl-4-methoxyphenylboronic acid

2-(1,3-dioxolan-2-yl)-4-(4-pyridinyl)anisole

4-bromopyridine hydrochloride

Downstream raw materials:

2-hydroxy-5-(4-pyridinyl)-benzaldehyde

cis-[4-(2-methoxy-5-pyridin-4-yl-benzylamino)-cyclohexyl]-carbamic acid tert-butyl ester