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

Chemical Properties

Off-white to light yellow crystal.

Uses

Different sources of media describe the Uses of 4487-59-6 differently. You can refer to the following data:
1. 2-Bromo-5-nitropyridine was used in preparation of boc-protected (piperazin-1-ylmethyl)biaryls via microwave-mediated Suzuki-Miyaura coupling with (boc-piperazin-1-ylmethyl)phenylboronic acid pinacol esters. It was also used in the synthesis of 2-pyridyl analogs. Substituted 5-nitro-2-ethynylpyridines were synthesized by the Sonogashira reaction of 2-bromo-5-5-nitropyridine with terminal acetylenes.
2. 2-Bromo-5-nitropyridine was used in preparation of boc-protected (piperazin-1-ylmethyl)biaryls via microwave-mediated Suzuki-Miyaura coupling with (boc-piperazin-1-ylmethyl)phenylboronic acid pinacol esters. It was also used in the synthesis of 2-pyridyl analogs.

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

• 163085-40-3 5-nitro-2-(2-pyridinylethynyl)pyridine 
• 82205-58-1 1-(5-nitro-2-pyridinyl)piperazine 
• 20168-70-1 u202fN,N-diethyl-5-nitropyridin-2-amine 
• 590424-16-1 2-(1-fluorovinyl)-5-nitropyridine 
• 790714-73-7 tert-butyl (5-nitropyridin-2-yl)acetate 
• 24242-20-4 5-amino-pyridine-2-carboxylic acid 
• 32046-43-8 5-Iodpicolinsaeure 
• 15069-92-8 5-hydroxypicolinic acid 
• 30766-11-1 5-bromoisonicotinic acid 
• 29082-92-6 5-methoxypyridine-2-carboxylic acid 
• 86873-62-3 5-Acetylaminopyridin-2-carbonsaeure 
• 86873-61-2 5-Hydroxylaminopyridin-2-carbonsaeure 
• 20885-21-6 3-nitro-6-(methylthio)pyridine 
• 131941-26-9 2-(4-methylphenyl)-5-nitropyridine 

Relevant articles and documents

Nitrosation of aryl and heteroaryltrifluoroborates with nitrosonium tetrafluoroborate

Organotrifluoroborates have emerged as an alternative to toxic and air- and moisture-sensitive organometallic species for the synthesis of functionalized aryl and heteroaryl compounds. It has been shown that the trifluoroborate moiety can be easily converted into a variety of different substituents in a late synthetic stage. In this paper, we disclose a mild, selective, and convenient method for the ipso-nitrosation of organotrifluoroborates using nitrosonium tetrafluoroborate (NOBF4). Aryl- and heteroaryltrifluoroborates were converted into the corresponding nitroso products in good to excellent yields. This method proved to be tolerant of a broad range of functional groups.

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.