4487-59-6

Basic information

• Product Name: 2-Bromo-5-nitropyridine
• Synonyms: TIMTEC-BB SBB003519;2-BROMO-5-NITROPYRIDINE;2-BROMO-5-NITROPYRIDINE 97%;2-BROMO-5-NITROPYRIDINE 2-BROMO-5-NITROPYRIDINE;2-BORMO-5-NITROPYRIDINE;2-bromo-5-mitropyridine;5-nitro-2-bromopyridin;2-BroMo-5-nitropyridine, 98% 1GR
• CAS NO: 4487-59-6
• Molecular Formula: C₅H₃BrN₂O₂
• Molecular Weight: 202.99
• EINECS: 224-777-2
• Product Categories: compounds of pyridine;pyridines;blocks;Bromides;NitroCompounds;pyridine derivative;Pyridines, Pyrimidines, Purines and Pteredines;Pyridine series;Halides;Pyridine;Pyridines derivates;Nucleotides and Nucleosides;Bromopyridines;Halopyridines;Bases & Related Reagents;Nucleotides;Boronic Acid;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Brominated heterocyclic series;Building Blocks/Intermediates
• Mol File: 4487-59-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 139-141 °C(lit.)
• Boiling Point: 145-147 °C10 mm Hg(lit.)
• Flash Point: 145-147°C/10mm
• Appearance: Light yellow to light brown/Crystalline Powder
• Density: 1.8727 (rough estimate)
• Vapor Pressure: 0.0322mmHg at 25°C
• Refractive Index: 1.6200 (estimate)
• Storage Temp.: Keep Cold
• Solubility: Chloroform, Hot Methanol
• PKA: -3.24±0.10(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 120901
• CAS DataBase Reference: 2-Bromo-5-nitropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-5-nitropyridine(4487-59-6)
• EPA Substance Registry System: 2-Bromo-5-nitropyridine(4487-59-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-37/39-22-36
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT, IRRITANT-HARMFUL
• PackingGroup: III
• Hazardous Substances Data: 4487-59-6(Hazardous Substances Data)

Usage

Description

2-Bromo-5-nitropyridine is an organic compound characterized by its off-white to light yellow crystalline appearance. It is a derivative of pyridine, a heterocyclic compound, with a bromine atom at the 2nd position and a nitro group at the 5th position. 2-Bromo-5-nitropyridine is known for its reactivity and is commonly utilized in various chemical synthesis processes.

Uses

Used in Pharmaceutical Industry:
2-Bromo-5-nitropyridine is used as a synthetic intermediate for the preparation of boc-protected (piperazin-1-ylmethyl)biaryls. This application is facilitated through microwave-mediated Suzuki-Miyaura coupling with (boc-piperazin-1-ylmethyl)phenylboronic acid pinacol esters. 2-Bromo-5-nitropyridine plays a crucial role in the development of new pharmaceuticals and therapeutic agents.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-Bromo-5-nitropyridine is employed in the synthesis of 2-pyridyl analogs. These analogs are essential in the development of various chemical compounds with potential applications in different industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Material Science:
2-Bromo-5-nitropyridine is also utilized in the synthesis of substituted 5-nitro-2-ethynylpyridines through the Sonogashira reaction with terminal acetylenes. These synthesized compounds have potential applications in material science, particularly in the development of new materials with unique properties and functionalities.

InChI:InChI=1/C5H3BrN2O2/c6-4-1-5(8(9)10)3-7-2-4/h1-3H

Upstream product

• 5418-51-9 5-nitro-2-hydroxypyridine 
• 4214-76-0 5-nitro-pyridin-2-ylamine 
• 223463-14-7 6-bromopyridin-3-ylboronic acid 
• 5418-51-9 5-nitro-2-pyridone 

Downstream Products

• 100367-55-3 5-nitropyridine-2-carbonitrile 
• 5446-92-4 2-methoxy-5-nitropyridine 
• 5418-51-9 5-nitro-2-hydroxypyridine 
• 163085-40-3 5-nitro-2-(2-pyridinylethynyl)pyridine 
• 82205-58-1 1-(5-nitro-2-pyridinyl)piperazine 
• 89076-64-2 3-nitro-6-phenylpyridine 
• 21203-68-9 2-methyl-5-nitropyridine 
• 857080-10-5 4-(5-nitropyridin-2-yl)benzenesulfonyl-L-valine t-butyl ester 
• 864075-95-6 3-(5-nitropyridin-2-yl)benzoic acid 
• 362617-28-5 phenylmethyl (S)-5-nitro-α-[[(phenylmethoxy)-carbonyl]amino]-2-pyridinebutanoate 
• 13534-97-9 6-bromopyridine-3-amine 
• 20168-70-1 u202fN,N-diethyl-5-nitropyridin-2-amine 
• 92-52-4 biphenyl 
• 31557-75-2 2-Acetyl-5-nitropyridin 

Relevant articles and documents

Benzoheterocyclic amodiaquine analogues with potent antiplasmodial activity: Synthesis and pharmacological evaluation

The synthesis and evaluation of antiplasmodial activity of benzothiazole, benzimidazole, benzoxazole and pyridine analogues of amodiaquine is hereby reported. Benzothiazole and benzoxazole analogues with a protonatable tertiary nitrogen atom possessed excellent activity against the W2 and K1 chloroquine resistant strains of Plasmodium falciparum, with IC50s ranging from 7 to 22 nM.

Nitropyridines: X.* Palladium-catalyzed cross-coupling of 2-bromo-5-nitropyridine with terminal acetylenes

Substituted 5-nitro-2-ethynylpyridines were synthesized by the Sonogashira reaction of 2-bromo-5-5-nitropyridine with terminal acetylenes. Desilylation, oxidative decarbonylation, and the retro-Favorskii reaction of the cross-coupling products of 2-bromo-5-nitropyridine with trimethylsilylacetylene, prop-2-ynyl alcohol, and 2-methylbut-3-yn-2-ol, respectively, gave 2-ethynyl-5-nitropyridine. The hydration of 2-ethynyl-5-nitropyridine and 5-nitro-2-(phenylethynyl)pyridine according to Kucherov afforded 2-acetyl-5-nitropyridine and 5-nitro-2-phenacylpyridine, respectively. Pleiades Publishing, Ltd., 2010.

The Synthesis of the High-Potency Sweetener, NC-00637. Part 2: Preparation of the Pyridine Moiety

The pyridine moiety within the high-potency sweetener, NC-00637 (1), 5-amino-2-cyanopyridine (4), was prepared from 2-hydroxy-5-nitropyridine (10). The sequence involved the conversion of the hydroxy group to bromide followed by substitution with cyanide to give 2-cyano-5-nitropyridine (8). Reduction of the nitro group proved to be troublesome when catalytic hydrogenation was used. Iron with an acid gave a reproducible reaction that could be used at scale.