2-Bromo-5-nitropyridine

Base Information

• Chemical Name: 2-Bromo-5-nitropyridine
• CAS No.: 4487-59-6
• Molecular Formula: C5H3BrN2O2
• Molecular Weight: 202.995
• Hs Code.: 29333990
• European Community (EC) Number: 224-777-2
• NSC Number: 73702
• DSSTox Substance ID: DTXSID10196327
• Nikkaji Number: J149.531C
• Wikidata: Q72448721
• Mol file: 4487-59-6.mol

Synonyms:2-bromo-5-nitro-pyridine;

Chemical Property of 2-Bromo-5-nitropyridine

Chemical Property:

• Appearance/Colour: Off-white to light yellow crystal
• Vapor Pressure: 0.0322mmHg at 25°C
• Melting Point: 139-141 °C(lit.)
• Refractive Index: 1.614
• Boiling Point: 289.312 °C at 760 mmHg
• PKA: -3.24±0.10(Predicted)
• Flash Point: 122.191 °C
• PSA: 58.71000
• Density: 1.834 g/cm³
• LogP: 2.27550
• Storage Temp.: Keep Cold
• Solubility.: Chloroform, Hot Methanol
• Water Solubility.: Insoluble in water.
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 201.93779
• Heavy Atom Count: 10
• Complexity: 136

Purity/Quality:

99% ^*data from raw suppliers

5-Nitro-2- ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-37/39-22-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=NC=C1[N+](=O)[O-])Br
• Uses: 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-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.

Technology Process of 2-Bromo-5-nitropyridine

There total 8 articles about 2-Bromo-5-nitropyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

2-(trifluoromethanesulfonyl)oxy-5-nitropyridine → 2-bromo-5-nitropyridine (4487-59-6)

Guidance literature:

With tetrabutylammomium bromide; In toluene; for 6h; Heating;

Reference yield: 70.0%

5-nitro-2-hydroxypyridine (5418-51-9) → 2-bromo-5-nitropyridine (4487-59-6) + 2,3-dibromo-5-nitropyridine (15862-36-9)

Guidance literature:

With bromine; phosphorus tribromide; In 1,2-dichloro-ethane; at 84 - 88 ℃; for 2h; Reflux; Industrial scale;

DOI:10.1021/op034110c

Reference yield: 48.0%

5-nitro-2-pyridone (5418-51-9) → 2-bromo-5-nitropyridine (4487-59-6)

Guidance literature:

With phosphorus pentoxide; tetrabutylammomium bromide; In benzene; for 1h; Regflux;

DOI:10.1134/S1070428010120109

upstream raw materials:

5-nitro-2-hydroxypyridine

5-nitro-pyridin-2-ylamine

5-nitro-2-pyridone

6-bromopyridin-3-ylboronic acid

Downstream raw materials:

6-butoxypyridin-3-ylamine

pyridin-3-ylamine

6-bromopyridine-3-amine

5-nitropyridine-2-carbonitrile

Refernces

• 1、 Molander, Gary A.,Cavalcanti, Livia N.. "Nitrosation of aryl and heteroaryltrifluoroborates with nitrosonium tetrafluoroborate". experimental part. p. 4402 - 4413. Retrieved 2012/06/18.
• 2、 -. "Therapeutic quinazoline derivatives". . . Retrieved 2008/06/13.