2-Ethynyl-5-nitropyridine

Base Information

• Chemical Name: 2-Ethynyl-5-nitropyridine
• CAS No.: 452333-53-8
• Molecular Formula: C₇H₄N₂O₂
• Molecular Weight: 148.121
• DSSTox Substance ID: DTXSID90514601
• Nikkaji Number: J1.724.427B
• Wikidata: Q82375027
• Mol file: 452333-53-8.mol

Synonyms:2-ethynyl-5-nitropyridine;452333-53-8;SCHEMBL2387319;DTXSID90514601;Pyridine,2-ethynyl-5-nitro-(9ci);AB68971;CS-0054123

Chemical Property of 2-Ethynyl-5-nitropyridine

Chemical Property:

• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 148.027277375
• Heavy Atom Count: 11
• Complexity: 200

Purity/Quality:

98%min ^*data from raw suppliers

2-Ethynyl-5-nitropyridine 95%+ ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C#CC1=NC=C(C=C1)[N+](=O)[O-]

Technology Process of 2-Ethynyl-5-nitropyridine

There total 6 articles about 2-Ethynyl-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: 90.0%

2-(2-(trimethylsilyl)ethynyl)-5-nitropyridine (201026-82-6) → 2-ethynyl-5-nitropyridine (452333-53-8)

Guidance literature:

With potassium fluoride; In ethanol; for 0.5h;

DOI:10.1134/S1070428010120109

Reference yield: 60.0%

4-trimethylsilyl-3-butyn-2-one (5930-98-3) + 3,5-dinitro-1-methyl-2-pyridone (14150-94-8) → 2-(2-(trimethylsilyl)ethynyl)-5-nitropyridine (201026-82-6) + 2-ethynyl-5-nitropyridine (452333-53-8)

Guidance literature:

With ammonium acetate; In ethanol; at 80 ℃; for 4h; Temperature; Overall yield = 84 %; Overall yield = 46.2 mg; Microwave irradiation;

DOI:10.1246/cl.150045

Reference yield: 42.0%

3-(5-nitropyridin-2-yl)prop-2-yn-1-ol (1279130-84-5) → 2-ethynyl-5-nitropyridine (452333-53-8)

Guidance literature:

With manganese(IV) oxide; potassium hydroxide; In benzene; at 20 ℃; for 3h;

DOI:10.1134/S1070428010120109

upstream raw materials:

2-bromo-5-nitropyridine

3-(5-nitropyridin-2-yl)prop-2-yn-1-ol

2-methyl-4-(5-nitropyridin-2-yl)but-3-yn-2-ol

5-nitro-2-pyridone

Refernces

• 1、 Sagitullina,Vorontsova,Garkushenko,Poendaev,Sagitullin. "Nitropyridines: X.* Palladium-catalyzed cross-coupling of 2-bromo-5-nitropyridine with terminal acetylenes". . p. 1830 - 1834. Retrieved 2011/04/15.