Methyl 2-(bromomethyl)nicotinate

Base Information

• Chemical Name: Methyl 2-(bromomethyl)nicotinate
• CAS No.: 116986-08-4
• Molecular Formula: C₈H₈BrNO₂
• Molecular Weight: 230.061
• DSSTox Substance ID: DTXSID80710271
• Wikidata: Q82645557
• Mol file: 116986-08-4.mol

Synonyms:Methyl 2-(bromomethyl)nicotinate;116986-08-4;METHYL 2-(BROMOMETHYL)PYRIDINE-3-CARBOXYLATE;3-Pyridinecarboxylic acid, 2-(bromomethyl)-, methyl ester;Methyl2-(bromomethyl)nicotinate;SCHEMBL4556786;DTXSID80710271;RPWHKHJDHYAYKG-UHFFFAOYSA-N;MFCD17214947;AKOS016000786;AB71758;DS-5913

Chemical Property of Methyl 2-(bromomethyl)nicotinate

Chemical Property:

• Boiling Point: 291.3±30.0 °C(Predicted)
• PKA: 1.40±0.22(Predicted)
• Density: 1.533±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 228.97384
• Heavy Atom Count: 12
• Complexity: 163

Purity/Quality:

97% ^*data from raw suppliers

Methyl2-(Bromomethyl)nicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(N=CC=C1)CBr

Technology Process of Methyl 2-(bromomethyl)nicotinate

There total 3 articles about Methyl 2-(bromomethyl)nicotinate 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: 80.6%

methyl 2-methylnicotinate (65719-09-7) → methyl 2-(bromomethyl)pyridine-3-carboxylate (116986-08-4)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 90 ℃; for 16h; Inert atmosphere;

Reference yield: 69.0%

methyl 2-(hydroxymethyl)nicotinate → methyl 2-(bromomethyl)pyridine-3-carboxylate (116986-08-4)

Guidance literature:

methyl 2-(hydroxymethyl)nicotinate; With phosphorus tribromide; In tetrahydrofuran; at 20 - 65 ℃; for 0.25h;

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 5 - 10 ℃; pH=7;

Reference yield:

3-bromo-2-picoline (38749-79-0) → methyl 2-(bromomethyl)pyridine-3-carboxylate (116986-08-4)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 16 h / 80 °C / 2585.81 Torr

2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 16 h / 90 °C / Inert atmosphere

With N-Bromosuccinimide; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); 2,2'-azobis(isobutyronitrile); triethylamine; In tetrachloromethane;

upstream raw materials:

methyl 2-methylnicotinate

3-bromo-2-picoline

Downstream raw materials:

tert‐butyl 2‐oxo‐1,5,7,8‐tetrahydro‐1,6‐naphthyridine‐6(2H)‐carboxylate

7,8-dihydro-5H-[1,6]naphthyridine-6-carboxylic acid tert-butyl ester

2-(phenoxymethyl)pyridine-3-carboxylic acid

5,6,7,8-tetrahydro-1,6-naphthyridine