3430-16-8

Basic information

• Product Name: 3-Bromo-5-methylpyridine
• Synonyms: 3-BROMO-5-METHYLPYRIDINE;5-BROMO-3-PICOLINE;3-Methyl-5-Bromopyridine;3-BROMO-5-METHYLPYRIDINE (3-BROMO-5-PICOLINE);3-Bromo-5-picoline 3-Bromo-5-methylpyridine;3-Bromo-5-methylpyridine ,98%;3-brmo-5-methylpyridine;Pyridine, 3-bromo-5-methyl-
• CAS NO: 3430-16-8
• Molecular Formula: C₆H₆BrN
• Molecular Weight: 172.02
• EINECS: 1312995-182-4
• Product Categories: Pyridine;Pyridines, Pyrimidines, Purines and Pteredines;Pyridines;Building Blocks;Halides;Boronic Acid;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Heterocycle-Pyridine series
• Mol File: 3430-16-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 16.5-16.7 °C
• Boiling Point: 110°C/25mmHg(lit.)
• Flash Point: 91 °C
• Appearance: Light yellow liquid
• Density: 1.4869
• Vapor Pressure: 0.533mmHg at 25°C
• Refractive Index: 1.5618
• Storage Temp.: Room temperature.
• PKA: 3.16±0.20(Predicted)
• CAS DataBase Reference: 3-Bromo-5-methylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-5-methylpyridine(3430-16-8)
• EPA Substance Registry System: 3-Bromo-5-methylpyridine(3430-16-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-41-22
• Safety Statements: 26-36/37/39-39
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 3430-16-8(Hazardous Substances Data)

Usage

Description

3-Bromo-5-methylpyridine is an organic compound belonging to the pyridine family, characterized by its light yellow liquid appearance. It is a derivative of pyridine with a bromine atom at the 3rd position and a methyl group at the 5th position. 3-Bromo-5-methylpyridine serves as an important intermediate in the synthesis of various pharmaceuticals and chemical compounds due to its unique structural properties.

Uses

Used in Pharmaceutical Industry:
3-Bromo-5-methylpyridine is used as an intermediate for the synthesis of pyridinyl pyrrole compounds, which are known as proton pump inhibitors. These compounds exhibit improved gastric acid secretion suppressive activity, making them valuable in the development of medications for treating conditions related to excessive stomach acid, such as gastroesophageal reflux disease (GERD) and peptic ulcers.
Used in Chemical Synthesis:
In addition to its pharmaceutical applications, 3-Bromo-5-methylpyridine can also be utilized as a building block in the synthesis of other organic compounds. Its unique structure allows for further functionalization and modification, making it a versatile starting material for the development of new chemical entities with potential applications in various industries, including agrochemicals, dyes, and materials science.

InChI:InChI=1/C6H6BrN/c1-5-2-6(7)4-8-3-5/h2-4H,1H3

Upstream product

• 3430-19-1 5-methylpyridin-3-amine 
• 108-99-6 3-Methylpyridine 
• 3430-18-0 2,5-dibromo-3-methylpyridine 
• 1171891-42-1 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 
• 625-92-3 3,5-dibromopyridine 
• 823-96-1 Trimethylboroxine 
• 591-22-0 3,5-Lutidine 

Downstream Products

• 73571-20-7 5-methyl-3-phenoxypyridine 
• 4808-70-2 5-methylpyridine-3-sulfonic acid 

Relevant articles and documents

A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics

The kinetics of quinuclidine displacement of BH3 from a wide range of Lewis base borane adducts have been measured. Parameterization of these rates has enabled the development of a nucleofugality scale (NFB), shown to quantify and predict the leaving group ability of a range of other Lewis bases. Additivity observed across a number of series R′3-nRnX (X = P, N; R′ = aryl, alkyl) has allowed the formulation of related substituent parameters (nfPB, nfAB), providing a means of calculating NFB values for a range of Lewis bases that extends far beyond those experimentally derived. The utility of the nucleofugality parameter is explored by the correlation of the substituent parameter nfPB with the hydrolyses rates of a series of alkyl and aryl MIDA boronates under neutral conditions. This has allowed the identification of MIDA boronates with heteroatoms proximal to the reacting center, showing unusual kinetic lability or stability to hydrolysis.

Regioselectivity in free radical bromination of unsymmetrical dimethylated pyridines

During a literature review some curious inconsistencies in the free radical bromination of picolines were noted. To achieve a better understanding of the mechanisms and regioselectivity we reran these reactions, extending our work to unsymmetrical lutidin

ANTIBACTERIAL AGENTS

Compounds of formula (I) have antibacterial activity wherein R represents hydrogen or 1, 2 or 3 optional substituents; W is =C(R1)- or =N-; R1 is hydrogen or an optional substituent and R2 is hydrogen, methyl, or fluorine; or R1 and R2 taken together are -CH2-, -CH2CH2-, -O-, or, in either orientation, -O- CH2- Or -OCH2CH2-; R3 is a radical of formula -(Alk1)m-(Z)p-(Alk2)n-Q wherein m, p and n are independently 0 or 1, provided that at least one of m, p and n is 1, Z is -O-, -S-, -S(O)-, -S(O2)-, -NH-, -N(CH3)-, -N(CH2CH3)-, -C(=O)-, -O-(C=O)-, -C(=O)-O-, or an optionally substituted divalent monocyclic carbocyclic or heterocyclic radical having 3 to 6 ring atoms; or an optionally substituted divalent bicyclic heterocyclic radical having 5 to 10 ring atoms; Alk1 and Alk2 are optionally substituted C1C6 alkylene, C2-C6 alkenylene, or C2-C6 alkynylene radicals, which may optionally terminate with or be interrupted by -O-, -S-, -S(O)-, -S(O2)-, -NH-, -N(CH3)-, or -N(CH2CH3)-; and Q is hydrogen, halogen, nitrile, or hydroxyl or an optionally substituted monocyclic carbocyclic or heterocyclic radical having 3 to 6 ring atoms; or an optionally substituted bicyclic heterocyclic radical having 5 to 10 ring atoms.