5-Bromo-2-methoxypyridine

Base Information

• Chemical Name: 5-Bromo-2-methoxypyridine
• CAS No.: 13472-85-0
• Molecular Formula: C6H6BrNO
• Molecular Weight: 188.024
• Hs Code.: 29349990
• DSSTox Substance ID: DTXSID60370559
• Nikkaji Number: J1.030.310I
• Wikidata: Q72446396
• Mol file: 13472-85-0.mol

Synonyms:Pyridine, 5-bromo-2-methoxy-;2-Methoxy-5-Bromopyridine;2-Methyloxy-5-bromopyridine;

Chemical Property of 5-Bromo-2-methoxypyridine

Chemical Property:

• Appearance/Colour: light yellow liquid
• Vapor Pressure: 0.545mmHg at 25°C
• Melting Point: 80ºC (12 mmHg)
• Refractive Index: n20/D 1.555(lit.)
• Boiling Point: 197 °C at 760 mmHg
• PKA: 1.04±0.10(Predicted)
• Flash Point: 72.9 °C
• PSA: 22.12000
• Density: 1.53 g/cm³
• LogP: 1.85270
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 186.96328
• Heavy Atom Count: 9
• Complexity: 89.1

Purity/Quality:

99% ^*data from raw suppliers

5-Bromo-2-methoxypyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=NC=C(C=C1)Br
• General Description: 5-Bromo-2-methoxypyridine serves as a key intermediate in the efficient synthesis of 5-functionalized 2-methoxypyridines via bromine–magnesium exchange using lithium tributylmagnesiate, enabling further transformation into bicyclic δ-lactams through allylation and ring-closing metathesis, highlighting its versatility in constructing biologically relevant heterocyclic frameworks.

Technology Process of 5-Bromo-2-methoxypyridine

There total 20 articles about 5-Bromo-2-methoxypyridine 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: 98.0%

2,5-dibromopyridine (624-28-2) + methanol (67-56-1) → 2-methoxy-5-bromopyridine (13472-85-0,1199266-76-6)

Guidance literature:

With sodium hydroxide; for 5h; Reflux;

Reference yield: 98.0%

→ 2-methoxy-5-bromopyridine (13472-85-0,1199266-76-6)

Guidance literature:

With sodium hydroxide;

Reference yield: 95.0%

2,5-dibromopyridine (624-28-2) → 2-methoxy-5-bromopyridine (13472-85-0,1199266-76-6)

Guidance literature:

With sodium methylate; In methanol; water;

upstream raw materials:

5-bromo2-nitropyridine

sodium methylate

2-methoxypyridine

2,5-dibromopyridine

Downstream raw materials:

(5-benzyloxy-2-methoxyphenyl)-(6-methoxypyridin-3-yl)methanol

(5-Benzyloxy-2-methoxyphenyl)-(5-bromo-2-methoxypyridin-4-yl)methanol

6-methoxy-3-pyridinecarboxaldehyde

(2-methoxyphenyl)(2-methoxypyrid-5-yl)methanol

Refernces

Efficient synthesis of 5-functionalised 2-methoxypyridines and their transformation to bicyclic d-lactams, both accessed using magnesium ?ate? complexes as key reagents

10.1055/s-0029-1217733

The research aims to develop a practical and noncryogenic method for synthesizing 5-functionalised 2-methoxypyridines from 5-bromo-2-methoxypyridine using lithium tributylmagnesiate ([n-Bu3Mg]Li) as the bromine–magnesium exchange reagent. The study explores the transformation of these compounds into bicyclic d-lactams, such as 1-substituted quinolizidin-4-ones and 3,5,8,8a-tetrahydro-1H-quinolin-2-ones, through allylation with lithium allyldibutylmagnesiate ([allyln-Bu2Mg]Li) followed by ring-closing metathesis (RCM). The research concludes that this method allows for the convenient synthesis of a wide range of 5-substituted 2-methoxypyridines and their subsequent conversion into biologically relevant bicyclic d-lactams, demonstrating the utility of magnesium ‘ate’ complexes in organic synthesis and providing a pathway for the creation of complex heterocyclic structures.