142404-82-8

Basic information

• Product Name: 2-ACETAMIDO-4-METHYL-5-BROMOPYRIDINE
• Synonyms: 2-ACETYLAMINO-5-BROMO-4-METHYLPYRIDINE;2-ACETAMIDO-4-METHYL-5-BROMOPYRIDINE;2-ACETAMIDO-5-BROMO-4-PICOLINE;N-(5-BROMO-4-METHYL-PYRIDIN-2-YL)-ACETAMIDE;2-Acetamido-5-bromo-gamma-picoline;2-Acetylamino-5-bromo-4-methylpyridine ,97%;2-Acetamido-5-bromo-4-methylpyridine;Acetamide,N-(5-bromo-4-methyl-2-pyridinyl)-
• CAS NO: 142404-82-8
• Molecular Formula: C₈H₉BrN₂O
• Molecular Weight: 229.07
• Product Categories: Pyridine;C7 and C8Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridines
• Mol File: 142404-82-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 151-155 °C(lit.)
• Boiling Point: 372.5 °C at 760 mmHg
• Flash Point: 179.1 °C
• Appearance: /
• Density: 1.545
• Vapor Pressure: 9.6E-06mmHg at 25°C
• Refractive Index: 1.606
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Chloroform
• PKA: 12.94±0.70(Predicted)
• CAS DataBase Reference: 2-ACETAMIDO-4-METHYL-5-BROMOPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ACETAMIDO-4-METHYL-5-BROMOPYRIDINE(142404-82-8)
• EPA Substance Registry System: 2-ACETAMIDO-4-METHYL-5-BROMOPYRIDINE(142404-82-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41-42/43
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 142404-82-8(Hazardous Substances Data)

Usage

Description

2-Acetamido-4-methyl-5-bromopyridine is an organic compound characterized by its white solid appearance. It is a derivative of pyridine, a heterocyclic compound with a nitrogen atom in the ring structure. The presence of the acetamido group at the 2nd position, a methyl group at the 4th position, and a bromine atom at the 5th position gives this compound unique chemical properties and potential applications in various industries.

Uses

Used in Chemical Synthesis:
2-Acetamido-4-methyl-5-bromopyridine is used as an intermediate in the synthesis of various organic compounds, particularly those with pharmaceutical or agrochemical applications. Its unique structure allows for further functionalization and modification to create a range of products with specific properties and uses.
Used in the Continuous Exothermix Process of Nitration:
In the chemical industry, 2-Acetamido-4-methyl-5-bromopyridine is utilized in the continuous exothermix process of nitration. This process involves the reaction of the compound with nitrating agents to introduce a nitro group (-NO2) into the molecule, which can enhance its reactivity and properties for specific applications.
Used in Pharmaceutical Research:
Due to its unique structure, 2-Acetamido-4-methyl-5-bromopyridine holds potential in the development of new pharmaceuticals. It can be used as a building block for the creation of novel drug candidates, particularly those targeting various diseases and conditions. Its chemical properties allow for further modification and optimization to improve the efficacy and safety of the resulting drug molecules.
Used in Agrochemical Development:
In the agrochemical industry, 2-Acetamido-4-methyl-5-bromopyridine can be employed as a starting material for the development of new pesticides, herbicides, or other crop protection agents. Its unique chemical structure can be tailored to target specific pests or weeds, providing more effective and selective control options for farmers and agricultural professionals.

InChI:InChI=1/C8H9BrN2O/c1-5-3-8(11-6(2)12)10-4-7(5)9/h3-4H,1-2H3,(H,10,11,12)

Upstream product

• 98198-48-2 2-amino-5-bromo-4-methylpyridine 
• 108-24-7 acetic anhydride 
• 5327-32-2 2-acetylamino-4-methylpyridine 
• 695-34-1 2-Amino-4-methylpyridine 
• 864830-16-0 5-bromo-2-fluoro-4-methyl-pyridine 
• 124-42-5 acetamidine hydrochloride 

Downstream Products

• 5327-32-2 2-acetylamino-4-methylpyridine 
• 1111637-72-9 6-acetamido-4-methylpyridin-3-ylboronic acid 
• 1171975-45-3 2-(acetylamino)-5-(4-t-butylphenyl)-4-picoline 
• 100367-40-6 2-amino-3-nitro-4-methyl-5-bromopyridine 
• 864953-39-9 1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium (3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)methyl hydrogen phosphate 
• 1392514-39-4 C₂₅H₂₄ClN₇O₄ 
• 917918-81-1 2-(5-bromo-2-methoxy-3-nitropyridin-4-yl)-N,N-dimethylethenamine 
• 917918-82-2 C₁₁H₁₅N₃O₄ 
• 1392514-36-1 C₂₁H₁₈ClN₅O₄S 
• 1392514-37-2 C₃₁H₂₈ClN₇O₄S 
• 98198-48-2 2-amino-5-bromo-4-methylpyridine 
• 884495-14-1 5-bromo-2-methoxy-4-methyl-3-nitropyridine 
• 228410-90-0 2-hydroxy-5-bromo-4-methyl-3-nitropyridine 
• 364046-14-0 4-[(2-di-N,N-methylamino)vinyl]-2-methoxy-3-nitropyridine 

Relevant articles and documents

The reaction of some brominated aminopicolines with acetic anhydride and with copper(I) cyanide

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Preparation of the HIV Attachment Inhibitor BMS-663068. Part 1. Evolution of Enabling Strategies

The development of two enabling routes that led to the production of >1000 kg of BMS-663068 (3) is described. The route identified for the initial 100 kg delivery to support development activities and initial clinical trials involved the conversion of 2-amino-4-picoline to the parent active pharmaceutical ingredient (API), followed by pro-drug installation and deprotection. To eliminate the problematic isolation of the parent API and synthesis of di-t-butyl(chloromethyl)phosphate, a second-generation pro-drug installation route was developed which involved the conversion of a late-stage common intermediate to an N(1)-thioether derivative followed by chloromethylation, displacement with di-t-butylpotassium phosphate, and deprotection. This second strategy resulted in the multikilogram scale preparation of the API in 14 linear steps and ～7% overall yield.

METHODS OF MAKING HIV ATTACHMENT INHIBITOR PRODRUG COMPOUND AND INTERMEDIATES

A method for making the compound of Formula ( I ) is set forth using alkylation, amidation, chlorination and phosphate installation procedures.