Methyl 4-methylnicotinate

Base Information

• Chemical Name: Methyl 4-methylnicotinate
• CAS No.: 33402-75-4
• Molecular Formula: C8H9NO2
• Molecular Weight: 151.165
• Hs Code.: 2933399990
• DSSTox Substance ID: DTXSID80446705
• Nikkaji Number: J481.289A
• Wikidata: Q72492887
• Mol file: 33402-75-4.mol

Synonyms:methyl 4-methylnicotinate;33402-75-4;Methyl 4-methylpyridine-3-carboxylate;MFCD09258869;4-Methyl-nicotinic acid methyl ester;Methyl 4-methyl-nicotinate;SCHEMBL1440123;DTXSID80446705;XEXPJABJVHEOCX-UHFFFAOYSA-N;BCP27135;AKOS005146332;CS-W003595;FS-2597;PB42565;SY030816;A5955;AM20051080;FT-0630173;4-Methylpyridine-3-carboxylic acid methyl ester

Chemical Property of Methyl 4-methylnicotinate

Chemical Property:

• Vapor Pressure: 0.149mmHg at 25°C
• Refractive Index: 1.51
• Boiling Point: 215.253 °C at 760 mmHg
• PKA: 3.86±0.18(Predicted)
• Flash Point: 83.983 °C
• PSA: 39.19000
• Density: 1.105 g/cm³
• LogP: 1.17660
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 151.063328530
• Heavy Atom Count: 11
• Complexity: 147

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl4-Methylnicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=NC=C1)C(=O)OC
• Uses: Methyl 4-Methylnicotinate, is an intermediate for the synthesis of various chemical compounds. It can be used for the preparation of pyridine analogs of Phthalide.

Technology Process of Methyl 4-methylnicotinate

There total 3 articles about Methyl 4-methylnicotinate 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: 9.5%

methanol (67-56-1) + methyl 3-pyridinecarboxylate (93-60-7) → 4-methylnicotinic acid methyl ester (33402-75-4) + Methyl 6-methylnicotinate (5470-70-2) + 2-methoxynicotinic acid methyl ester (67367-26-4) + 6-methoxy-nicotinic acid methyl ester (26218-80-4)

Guidance literature:

With sulfuric acid; for 1h; Product distribution; Mechanism; Irradiation; effect of additives; variation of temp., acid concn.; further alcohol;

DOI:10.1246/cl.1980.131

Reference yield:

methyl 3-pyridinecarboxylate (93-60-7) + methylmagnesium chloride (676-58-4) + phenyl chloroformate (1885-14-9) → 4-methylnicotinic acid methyl ester (33402-75-4) + Methyl 6-methylnicotinate (5470-70-2)

Guidance literature:

With sulfur; Yield given. Multistep reaction;

Reference yield:

3-cyano-4-methylpyridine (5444-01-9) → 4-methylnicotinic acid methyl ester (33402-75-4)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydroxide; water

2: sulfuric acid / Reflux

With sulfuric acid; water; potassium hydroxide;

DOI:10.1016/j.tet.2013.06.029

upstream raw materials:

methanol

methyl 3-pyridinecarboxylate

methylmagnesium chloride

phenyl chloroformate

Downstream raw materials:

(4-methylpyridin-3-yl)methanol

C₁₂H₂₁NO₄

1-chloro-4-iodo-2,7-diazanaphthalene

4-iodine-2,7-naphthyridine-1(2H)-one

Refernces

• 1、 Comins, Daniel L.,Stroud, Eric D.,Herric, James J.. "Regioselective addition of Grignard reagents to the 1-phenoxycarbonyl salts of alkyl nikotinates". . p. 151 - 157. Retrieved 2007/10/02.
• 2、 Sugiyama, Toru,Tobita, Estuo,Takagi, Kyoko,Sato, Michitsugu,Kumagai, Yasuyuki,et al.. "MULTIPLE PATHS FOR PHOTOALKYLATION OF PYRIDINECARBOXYLIC ESTERS IN ALCOHOLS". . p. 131 - 134. Retrieved 2007/10/02.