Methyl 5-chloro-2-methylnicotinate

Base Information

• Chemical Name: Methyl 5-chloro-2-methylnicotinate
• CAS No.: 350597-49-8
• Molecular Formula: C8H8ClNO2
• Molecular Weight: 185.61
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID00446383
• Nikkaji Number: J1.544.283B
• Wikidata: Q82265009
• Mol file: 350597-49-8.mol

Synonyms:methyl 5-chloro-2-methylnicotinate;350597-49-8;methyl5-chloro-2-methylnicotinate;methyl 5-chloro-2-methylpyridine-3-carboxylate;5-Chloro-2-methylnicotinic acid methyl ester;5-Chrolo-2-methyl nicotinic acid methyl ester;MFCD09908061;5-CHLORO-2-METHYL-NICOTINIC ACID METHYL ESTER;3-PYRIDINECARBOXYLIC ACID, 5-CHLORO-2-METHYL-, METHYL ESTER;SCHEMBL401530;DTXSID00446383;KYEIGXOFICMHDP-UHFFFAOYSA-N;BCP00991;AKOS006310847;CS-W005667;FS-2396;AC-22844;SY047645;A6151;AM20051107;FT-0651560;2-Methyl-5-chloropyridine-3-carboxylic acid methyl ester

Chemical Property of Methyl 5-chloro-2-methylnicotinate

Chemical Property:

• Vapor Pressure: 0.0558mmHg at 25°C
• Melting Point: 45-47℃
• Refractive Index: 1.528
• Boiling Point: 233.5 °C at 760 mmHg
• PKA: 1.63±0.20(Predicted)
• Flash Point: 95 °C
• PSA: 39.19000
• Density: 1.248 g/cm³
• LogP: 1.83000
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 185.0243562
• Heavy Atom Count: 12
• Complexity: 174

Purity/Quality:

99% ^*data from raw suppliers

Methyl 5-chloro-2-methylnicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=C(C=N1)Cl)C(=O)OC

Technology Process of Methyl 5-chloro-2-methylnicotinate

There total 4 articles about Methyl 5-chloro-2-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: 80.0%

acetoacetic acid methyl ester (105-45-3) + N-(2-chloro-3-(dimethylamino)allylidene)-N-methylmethanaminium hexafluorophosphate(V) → 2-methyl-5-chloro methylnicotinate (350597-49-8)

Guidance literature:

acetoacetic acid methyl ester; With potassium tert-butylate; In tetrahydrofuran; at 0 - 20 ℃; for 1.16h;

N-(2-chloro-3-(dimethylamino)allylidene)-N-methylmethanaminium hexafluorophosphate(V); With 1,4-diaza-bicyclo[2.2.2]octane; In tetrahydrofuran; at 45 ℃; for 3h;

With ammonium acetate; In tetrahydrofuran; at 45 - 80 ℃; for 5h;

Reference yield:

acetoacetic acid methyl ester (105-45-3) + (Z)-N-(2-chloro-3-(dimethylamino)allylidene)-N-methylmethanaminium hexafluorophosphate → 2-methyl-5-chloro methylnicotinate (350597-49-8)

Guidance literature:

acetoacetic acid methyl ester; With potassium tert-butylate; In tetrahydrofuran; at 0 - 5 ℃; for 0.666667h;

(Z)-N-(2-chloro-3-(dimethylamino)allylidene)-N-methylmethanaminium hexafluorophosphate; With acetic acid; trifluoroacetic acid; In tetrahydrofuran; for 0.75h;

With ammonia; water; In tetrahydrofuran; for 0.75h; Heating / reflux;

Reference yield:

(2E,4Z)-2-Acetyl-4-chloro-5-dimethylamino-penta-2,4-dienoic acid methyl ester (325855-84-3) → 2-methyl-5-chloro methylnicotinate (350597-49-8)

Guidance literature:

With ammonium acetate; In tetrahydrofuran; for 6h; Heating;

DOI:10.1021/jo0155198

upstream raw materials:

(2E,4Z)-2-Acetyl-4-chloro-5-dimethylamino-penta-2,4-dienoic acid methyl ester

acetoacetic acid methyl ester

Downstream raw materials:

(5-chloro-2-methylpyridin-3-yl)methanol

3-chloro-7-[(2,4-dimethoxybenzyl)amino]-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one

N-((2R)-1,4-dioxan-2-ylmethyl)-N-methyl-N’-[3-(1-methyl-1H-pyrazol-4-yl)-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl]sulfamide

N-methyl-N'-[3-(1-methyl-1H-pyrazol-4-yl)-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl]-N-(pyrazin-2-ylmethyl)sulfuric diamide

Refernces

• 1、 -. "(3-HYDROXY-4-AMINO-BUTAN-2-YL) -3- (2-THIAZOL-2-YL-PYRROLIDINE-1-CARBONYL) BENZAMIDE DERIVATIVES AND RELATED COMPOUNDS AS BETA-SECRETASE INHIBITORS FOR TREATING". Page/Page column 106-107. . Retrieved 2009/05/29.
• 2、 Marcoux,Marcotte,Wu,Dormer,Davies,Hughes,Reider. "A general preparation of pyridines and pyridones via the annulation of ketones and esters". . p. 4194 - 4199. Retrieved 2007/10/03.