100367-40-6

Basic information

• Product Name: 2-Amino-5-bromo-4-methyl-3-nitropyridine
• Synonyms: 2-PYRIDINAMINE, 5-BROMO-4-METHYL-3-NITRO-;2-AMINO-5-BROMO-3-NITRO-4-PICOLINE;2-AMINO-5-BROMO-4-METHYL-3-NITROPYRIDINE;2-AMINO-3-NITRO-5-BROMO-4-PICOLINE;2-Amino-5-bromo-4-methyl-3-nitropyridine 98%;2-Amino-5-bromo-3-nitro-GAMMA-picoline;5-bromo-4-methyl-3-nitro-2-Pyridinamine;2-AMINO-3-NITRO-4-METHYL-5-BROMOPYRIDINE
• CAS NO: 100367-40-6
• Molecular Formula: C₆H₆BrN₃O₂
• Molecular Weight: 232.03
• EINECS: -0
• Product Categories: Amines;blocks;Bromides;Pyridines;Pyridine;CHIRAL CHEMICALS;Aromatics;Miscellaneous Reagents
• Mol File: 100367-40-6.mol
• Article Data: 17

Chemical Properties

• Melting Point: 160-164
• Boiling Point: 314.1 °C at 760 mmHg
• Flash Point: 143.8 °C
• Appearance: /
• Density: 1.795 g/cm³
• Vapor Pressure: 0.000476mmHg at 25°C
• Refractive Index: 1.658
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• PKA: 0.78±0.50(Predicted)
• CAS DataBase Reference: 2-Amino-5-bromo-4-methyl-3-nitropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-bromo-4-methyl-3-nitropyridine(100367-40-6)
• EPA Substance Registry System: 2-Amino-5-bromo-4-methyl-3-nitropyridine(100367-40-6)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 100367-40-6(Hazardous Substances Data)

Usage

General Description

2-Amino-5-bromo-4-methyl-3-nitropyridine is a chemical compound with the molecular formula C6H6BrN3O2. It is a yellow solid with a molecular weight of 216.03 g/mol. 2-Amino-5-bromo-4-methyl-3-nitropyridine is commonly used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. It contains functional groups such as an amino group, a nitro group, and a bromine atom, making it suitable for various chemical reactions. 2-Amino-5-bromo-4-methyl-3-nitropyridine is also known to possess antimicrobial and anti-inflammatory properties and has potential applications in the development of new drugs. Its structure and properties make it a versatile building block in organic synthesis.

InChI:InChI=1/C6H6BrN3O2/c1-3-4(7)2-9-6(8)5(3)10(11)12/h2H,1H3,(H2,8,9)

Upstream product

• 98198-48-2 2-amino-5-bromo-4-methylpyridine 
• 695-34-1 2-Amino-4-methylpyridine 
• 6635-86-5 2-amino-4-methyl-3-nitropyridine 
• 5327-32-2 2-acetylamino-4-methylpyridine 
• 142404-82-8 N-(5-bromo-4-methylpyridin-2-yl)acetamide 
• 923929-10-6 5-bromo-2-nitramino-4-picoline 

Downstream Products

• 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 
• 884495-14-1 5-bromo-2-methoxy-4-methyl-3-nitropyridine 
• 228410-90-0 2-hydroxy-5-bromo-4-methyl-3-nitropyridine 
• 116605-69-7 7-bromo-8-methylpyrido[2,3-b]pyrazine 
• 701213-36-7 1-(4-benzoylpiperazin-1-yl)-2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-ethane-1,2-dione 
• 364046-14-0 4-[(2-di-N,N-methylamino)vinyl]-2-methoxy-3-nitropyridine 
• 1445993-96-3 ethyl 4-bromo-6-methyl-7-oxo-1-toluenesulfonyl-6,7-dihydro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate 
• 1622303-45-0 4-(tert-butyl)-N-(2-(hydroxymethyl)-3-(6-methyl-7-oxo-1-tosyl-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)phenyl)benzamide 
• 1622303-44-9 4-(tert-butyl)-N-(2-(((tert-butyldimethylsilyl)oxy)methyl)-3-(6-methyl-7-oxo-1-tosyl-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)phenyl)benzamide 

Relevant articles and documents

An alternate route to 2-amino-3-nitro-5-bromo-4-picoline: Regioselective pyridine synthesis via 2-nitramino-picoline intermediate

The 2-nitramino functionality in 2-nitramino-4-picoline was successfully exploited not only as a protecting group but also as a directional handle to afford an efficient, atom-economic, and regioselective synthesis of 2-amino-5-bromo-3-nitro-4-picoline (4), a precursor for a drug candidate in development.

QUINOXALINE DERIVATIVES AS MODULATORS OF THE GLUCOCORTICOID RECEPTOR

The present invention relates to compounds according to general formula (I) which act as modulators of the glucocorticoid receptor and can be used in the treatment and/or prophylaxis of disorders which are at least partially mediated by the glucocorticoid receptor.

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.