4-Bromo-2-methylpyridine

Base Information

• Chemical Name: 4-Bromo-2-methylpyridine
• CAS No.: 22282-99-1
• Molecular Formula: C6H6BrN
• Molecular Weight: 172.024
• Hs Code.: 29333990
• European Community (EC) Number: 624-896-3
• DSSTox Substance ID: DTXSID20376496
• Nikkaji Number: J2.921.672J
• Wikidata: Q72447833
• ChEMBL ID: CHEMBL2087645
• Mol file: 22282-99-1.mol

Synonyms:4-Bromo-2-methylpyridine;22282-99-1;4-Bromo-2-picoline;2-Methyl-4-bromopyridine;4-bromo-2-methyl-pyridine;Pyridine, 4-bromo-2-methyl-;MFCD03788196;4-bromopicoline;4bromo-2-methylpyridine;4-bromo-2-methylpyridin;4-bromo-6-methylpyridine;4-bromo-2-methyl pyridine;SCHEMBL156475;CHEMBL2087645;DTXSID20376496;4-Bromo-2-methylpyridine, 96%;JFBMFWHEXBLFCR-UHFFFAOYSA-N;BCP22098;AC-188;AKOS005146001;CS-W007447;PB26077;PS-6174;SY002014;AM20050965;B3279;FT-0650271;EN300-82850;AN-584/43413320;Q-101489

Chemical Property of 4-Bromo-2-methylpyridine

Chemical Property:

• Appearance/Colour: Light yellow liquid
• Vapor Pressure: 0.581mmHg at 25°C
• Refractive Index: n 20/D 1.556
• Boiling Point: 195.7 °C at 760 mmHg
• PKA: 4.38±0.10(Predicted)
• Flash Point: 72.1 °C
• PSA: 12.89000
• Density: 1.494 g/cm³
• LogP: 2.15250
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Dichloromethane
• Water Solubility.: Miscible with dichloromethane. Immiscible with water.
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 170.96836
• Heavy Atom Count: 8
• Complexity: 74.9

Purity/Quality:

99% ^*data from raw suppliers

4-Bromo-2-picoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41-36/37/38-20/21/22
• Safety Statements: 26-36/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC=CC(=C1)Br
• Uses: 4-Bromo-2-methylpyridine is a starting material used in a synthesis of crown-ester-bipyridines and viologens via sodium or nickel reductive coupling, side chain oxidation and esterification. Used in the preparation of phenyloxadiazolyl pyridines as immunomodulating agents. 4-Bromo-2-methylpyridine is used as a starting material in the preparation of crown-ester-bipyridines and viologens through sodium or nickel reductive coupling, side chain oxidation and esterification. Further, it serves as an important raw material and intermediate in organic synthesis, pharmaceuticals, agrochemicals and in dyes.

Technology Process of 4-Bromo-2-methylpyridine

There total 15 articles about 4-Bromo-2-methylpyridine 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: 95.0%

3-methyl-4-pyridinamine (18437-58-6) → 4-bromo-2-methylpyridine (22282-99-1)

Guidance literature:

With hydrogen bromide; bromine; at -5 ℃;

Reference yield: 76.0%

2,4-dibromopyridine (58530-53-3) + methyl iodide (74-88-4) → 4-bromo-2-methylpyridine (22282-99-1)

Guidance literature:

2,4-dibromopyridine; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;

methyl iodide; In tetrahydrofuran; at -78 - 20 ℃;

Reference yield: 61.0%

2-methyl-4-nitro-pyridine (13508-96-8) → 4-bromo-2-methylpyridine (22282-99-1)

Guidance literature:

With Acetyl bromide; for 6h; Heating;

DOI:10.1248/cpb.38.2446

upstream raw materials:

3-methyl-4-pyridinamine

2-methyl-4-nitro-pyridine

Acetyl bromide

chloroform

Downstream raw materials:

2-(2-hydroxy-ethyl)-pyridin-4-ol

2-(4-bromopyridin-2-yl)ethanol

4-bromo-2-methylpyridine N-oxide

4-bromo-2-pyridinecarboxaldehyde

Refernces

• 1、 -. "2-methyl-4-bromopyridine preparation method". Paragraph 0015; 0018; 0021-0022; 0025-0026; 0029. . Retrieved 2020/02/06.
• 2、 -. "NOVEL ORGANIC COMPOUND AND MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES COMPRISING THE SAME AND ORGANIC ELECTROLUMINESCENT DEVICES COMPRISING THE SAME". Paragraph 0099; 0130-0133. . Retrieved 2020/11/24.