2-Chloro-5-ethynylpyridine

Base Information

• Chemical Name: 2-Chloro-5-ethynylpyridine
• CAS No.: 263012-63-1
• Molecular Formula: C7H4 Cl N
• Molecular Weight: 137.568
• European Community (EC) Number: 866-998-2
• DSSTox Substance ID: DTXSID50442971
• Nikkaji Number: J1.553.475C
• Wikidata: Q82260609
• Mol file: 263012-63-1.mol

Synonyms:2-Chloro-5-ethynylpyridine;263012-63-1;2-chloro-5-ethynyl-pyridine;PYRIDINE, 2-CHLORO-5-ETHYNYL-;MFCD10698136;Pyridine, 2-chloro-5-ethynyl- (9CI);2-chloro-5-ethynyl pyridine;SCHEMBL403343;DTXSID50442971;PGLDMOFVMPWSEN-UHFFFAOYSA-N;AMY14107;AKOS006303183;AB61374;CS-W007084;DS-4513;FT-0746607;EN300-201245;A849319

Chemical Property of 2-Chloro-5-ethynylpyridine

Chemical Property:

• Vapor Pressure: 0.31mmHg at 25°C
• Refractive Index: 1.567
• Boiling Point: 208.335°C at 760 mmHg
• Flash Point: 99.269°C
• PSA: 12.89000
• Density: 1.232g/cm³
• LogP: 1.71630
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 137.0032268
• Heavy Atom Count: 9
• Complexity: 135

Purity/Quality:

98%min ^*data from raw suppliers

2-Chloro-5-ethynylpyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CC1=CN=C(C=C1)Cl
• Uses: 2-Chloro-5-ethynylpyridine was used in the synthesis of conjugatively bridged bis- and tris-5-(2,2’bipyridines) multitopic metal Ion-binding modules for supramolecular nanoengineering. 2-Chloro-5-ethynylpyridine was used in the synthesis of conjugatively bridged bis- and tris-5-(2,2’-bipyridines) multitopic metal Ion-binding modules for supramolecular nanoengineering.

Technology Process of 2-Chloro-5-ethynylpyridine

There total 6 articles about 2-Chloro-5-ethynylpyridine 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: 95.0%

2-chloro-5-[(trimethylsilyl)ethynyl]-2,2'-bipyridine (263012-81-3) → 2-chloro-5-ethynylpyridine (263012-63-1)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 24h;

DOI:10.1021/jo990665n

Reference yield:

2-choro-5-iodopyridine (69045-79-0) → 2-chloro-5-ethynylpyridine (263012-63-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / 48 h / 20 °C

2: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 24 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; copper(l) iodide; triethylamine; In tetrahydrofuran; methanol; 1: Sonogashira reaction;

DOI:10.1021/jo001777d

Reference yield:

2-methyl-5-((trimethylsilyl)ethynyl)benzo[d]oxazole → 2-chloro-5-ethynylpyridine (263012-63-1)

Guidance literature:

With methanol; potassium carbonate; at 20 ℃; for 1h;

DOI:10.1021/acs.orglett.5b01370

upstream raw materials:

2-chloro-5-[(trimethylsilyl)ethynyl]-2,2'-bipyridine

2-choro-5-iodopyridine

5-bromo-2-chloropyridine

5-iodo-pyridin-2-ol

Downstream raw materials:

2-chloro-5-[(2-trimethylsilylethynylphenyl)ethynyl]pyridine

4-[4-(6-chloropyridin-3-yl)buta-1,3-diynyl]benzoic acid

6-ethynyl-3,3-difluoro-2-(4-(thiophen-2-yl)benzylidene)-2,3-dihydro[1,2,4,3]triazaborolo[4,5-a]pyridin-2-ium-3-uide

5-ethynyl-2-(2-(4-(thiophen-2-yl)benzylidene)hydrazinyl)pyridine

Refernces

• 1、 -. "PCSK9 INHIBITORS AND METHODS OF USE THEREOF". Page/Page column 187; 188. . Retrieved 2020/07/31.
• 2、 Tran, Ga?l,Gomez Pardo, Domingo,Tsuchiya, Tomoki,Hillebrand, Stefan,Vors, Jean-Pierre,Cossy, Janine. "Modular, Concise, and Efficient Synthesis of Highly Functionalized 5-Fluoropyridazines by a [2 + 1]/[3 + 2]-Cycloaddition Sequence". supporting information. p. 3414 - 3417. Retrieved 2015/07/28.