Methyl 2-(broMoMethyl)nicotinate

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Methyl 2-(broMoMethyl)nicotinate Basic information
Product Name:Methyl 2-(broMoMethyl)nicotinate
Synonyms:Methyl 2-(broMoMethyl)nicotinate;3-Pyridinecarboxylic acid, 2-(broMoMethyl)-, Methyl ester;METHYL 2-(BROMOMETHYL)PYRIDINE-3-CARBOXYLATE
CAS:116986-08-4
MF:C8H8BrNO2
MW:230.06
EINECS:
Product Categories:
Mol File:116986-08-4.mol
Methyl 2-(broMoMethyl)nicotinate Structure
Methyl 2-(broMoMethyl)nicotinate Chemical Properties
Boiling point 291.3±30.0 °C(Predicted)
density 1.533±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
pka1.40±0.22(Predicted)
AppearanceWhite to off-white Solid
Safety Information
MSDS Information
Methyl 2-(broMoMethyl)nicotinate Usage And Synthesis
Synthesis
Methyl 2-methylnicotinate

65719-09-7

Methyl 2-(broMoMethyl)nicotinate

116986-08-4

General procedure for the synthesis of methyl 2-(bromomethyl)nicotinate from methyl 2-methylnicotinate: methyl 2-methylnicotinate (4.1 g, 27.1 mmol), N-bromosuccinimide (NBS, 5.8 g, 32.5 mmol) and azobisisobutyronitrile (AIBN, 100 mg, 0.61 mmol) were dissolved in carbon tetrachloride (55 mL). The reaction mixture was stirred at 90 °C for 16 h under nitrogen protection. Upon completion of the reaction, it was cooled to room temperature and the reaction mixture was diluted with water (25 mL), followed by extraction of the aqueous layer with dichloromethane (50 mL x 3). The organic layers were combined and concentrated under reduced pressure to remove the solvent, and the resulting crude product was purified by silica gel column chromatography to afford the target product methyl 2-(bromomethyl)nicotinate (5.0 g, 80.6% yield). The product was analyzed by LCMS, m/z: 229.9 ([M+H]+).

References[1] Patent: WO2015/200677, 2015, A2. Location in patent: Paragraph 00522; 00523
[2] Tetrahedron Letters, 1981, vol. 22, # 50, p. 5097 - 5100
[3] Journal fuer Praktische Chemie (Leipzig), 1987, vol. 329, # 4, p. 557 - 562
[4] Patent: WO2012/61169, 2012, A1. Location in patent: Page/Page column 49
Methyl 2-(broMoMethyl)nicotinate Preparation Products And Raw materials
Raw materialsMethyl 2-methylnicotinate-->3-Bromo-2-methylpyridine-->Carbon tetrachloride-->AIBN-->N-Bromosuccinimide
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methyl 6-(bromomethyl)nicotinate Methyl 2-(chloromethyl)nicotinate 3-Pyridinecarboxylic acid, 2-(bromomethyl)- Ethyl 2-(broMoMethyl)nicotinate Ethyl 2-(bromomethyl)nicotinate hydrochloride Methyl 5-broMo-2-(broMoMethyl)pyridine-3-carboxylate