Methyl 5-formylpyridine-3-carboxylate

Base Information

• Chemical Name: Methyl 5-formylpyridine-3-carboxylate
• CAS No.: 6221-06-3
• Molecular Formula: C8H7NO3
• Molecular Weight: 165.148
• DSSTox Substance ID: DTXSID90599493
• Wikidata: Q82495382
• Mol file: 6221-06-3.mol

Synonyms:Methyl 5-formylpyridine-3-carboxylate;6221-06-3;Methyl 5-Formylnicotinate;5-Formyl Nicotinic Acid Methyl Ester;5-FORMYL-NICOTINIC ACID METHYL ESTER;Methyl5-Formylnicotinate;SCHEMBL2475641;DTXSID90599493;VLRLIUOJJSNOCS-UHFFFAOYSA-N;MFCD11100668;AKOS006307655;SB21411;AS-53254;DB-073067;CS-0048980;EN300-332066;P16250;Z1198311040

Chemical Property of Methyl 5-formylpyridine-3-carboxylate

Chemical Property:

• Melting Point: 85-91oC
• Boiling Point: 286.1±25.0 °C(Predicted)
• PKA: 1.39±0.20(Predicted)
• PSA: 56.26000
• Density: 1.249±0.06 g/cm3(Predicted)
• LogP: 0.68070
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Dichloromethane, Ethyl Acetate (Slightly), Methanol
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 165.042593085
• Heavy Atom Count: 12
• Complexity: 181

Purity/Quality:

97% ^*data from raw suppliers

5-FormylNicotinicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CN=CC(=C1)C=O
• Uses: 5-Formyl Nicotinic Acid Methyl Ester (cas# 6221-06-3) is a compound useful in organic synthesis.

Technology Process of Methyl 5-formylpyridine-3-carboxylate

There total 9 articles about Methyl 5-formylpyridine-3-carboxylate 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: 61.0%

methyl 5-(hydroxymethyl)pyridine-3-carboxylate (129747-52-0) → methyl 5-formylpyridine-3-carboxylate (6221-06-3)

Guidance literature:

With silica gel; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 6h;

Reference yield: 33.0%

5-bromo-3-pyridine carboxylic acid methyl ester (29681-44-5) + tert-butylisonitrile (119072-55-8,7188-38-7) → methyl 5-formylpyridine-3-carboxylate (6221-06-3)

Guidance literature:

With triethylsilane; palladium diacetate; sodium carbonate; CyJohnPhos; In N,N-dimethyl-formamide; at 65 ℃; Inert atmosphere;

Reference yield: 15.0%

5-bromo-3-pyridine carboxylic acid methyl ester (29681-44-5) + carbon monoxide (201230-82-2) → methyl 5-formylpyridine-3-carboxylate (6221-06-3)

Guidance literature:

With triethylsilane; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In acetonitrile; at 60 ℃; for 5h; under 1034.32 Torr;

upstream raw materials:

5-bromo-3-pyridine carboxylic acid methyl ester

carbon monoxide

(Z)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-isopropyl-3-benzyloxybenzylamine hydrochloride

methyl 5-(hydroxymethyl)pyridine-3-carboxylate

Downstream raw materials:

5-formylpyridine-3-carboxylic acid