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

Chemical Properties

Light yellow liquid

Uses

5-Bromo-3-picoline is an intermediate of pyridinyl pyrrole compounds as proton pump inhibitors with improved gastric acid secretion suppressive activity

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

• 566198-34-3 5-(3-formylphenyl)-nicotinic acid 
• 566198-40-1 5-(2-formylphenyl)-nicotinic acid 
• 566198-28-5 5-(4-formylphenyl)-nicotinic acid 
• 866683-92-3 3-methyl-5-(phenylethynyl)pyridine 
• 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

Meta halogenation of 1,3-disubstituted arenes via iridium-catalyzed arene borylation

We report the meta halogenation of 1,3-disubstituted arenes to form 3,5-disubstituted aryl bromides and chlorides by using iridium-catalyzed arene borylation chemistry. Iridium-catalyzed borylation of arenes with B2pin2, followed by reaction of the boronic ester with copper(II) bromide or chloride converts arylboronic esters to the corresponding aryl halides. A variety of arenes containing alkoxy, alkyl, halogen, nitrile, ester, amide, and pivaloyl and TIPS-protected alcohols were converted to the corresponding 3,5-disubstituted aryl bromides and chlorides in yields ranging from 46% to 85%. In addition, 2,6-disubstituted and 3-substituted pyridines were converted to the 4-halo and 5-halopyridines, respectively. The utility of this methodology was demonstrated by the formal conversion of nicotine to Altinicline in three steps with an overall yield of 61% using meta bromination of nicotine as the first step. Copyright