5-Bromo-2-ethynylpyridine

Base Information

• Chemical Name: 5-Bromo-2-ethynylpyridine
• CAS No.: 111770-86-6
• Molecular Formula: C7H4BrN
• Molecular Weight: 182.019
• European Community (EC) Number: 834-075-3
• DSSTox Substance ID: DTXSID40553707
• Nikkaji Number: J2.391.639H
• Wikidata: Q72455598
• Mol file: 111770-86-6.mol

Synonyms:5-bromo-2-ethynylpyridine;111770-86-6;5-bromo-2-ethynyl-pyridine;MFCD03095276;PYRIDINE, 5-BROMO-2-ETHYNYL-;SCHEMBL2327695;DTXSID40553707;VGLAJERHBBEPQP-UHFFFAOYSA-N;BCP26507;AKOS006237138;AB13647;AM85481;FS-3661;SY024562;B5179;CS-0043016;A15117;EN300-313219;J-002625;F2167-5076

Chemical Property of 5-Bromo-2-ethynylpyridine

Chemical Property:

• Appearance/Colour: Light yellow liquid
• Vapor Pressure: 0.256mmHg at 25°C
• Melting Point: 84-86℃
• Refractive Index: 1.609
• Boiling Point: 212.1 °C at 760 mmHg
• PKA: -0.09±0.22(Predicted)
• Flash Point: 82.1 °C
• PSA: 12.89000
• Density: 1.6 g/cm³
• LogP: 1.82540
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 180.95271
• Heavy Atom Count: 9
• Complexity: 135

Purity/Quality:

96% GC ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CC1=NC=C(C=C1)Br
• Uses: 5-Bromo-2-ethynylpyridine is used in the synthesis of anti-infective agents for the treatment of infectious diseases.

Technology Process of 5-Bromo-2-ethynylpyridine

There total 4 articles about 5-Bromo-2-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: 94.0%

3-bromo-6-(trimethylsilylethynyl)pyridine (111770-80-0) → 2-ethynyl-5-bromo-pyridine (111770-86-6)

Guidance literature:

With sodium hydroxide; In methanol; for 2h; Ambient temperature;

DOI:10.1021/jo00237a029

Reference yield: 78.0%

2-(tert-butyldimethylsilylethynyl)-5-bromopyridine (866929-82-0) → 2-ethynyl-5-bromo-pyridine (111770-86-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1039/c3cc46587j

Reference yield:

2-iodo-5-bromopyridine (223463-13-6) + trimethylsilylacetylene (1066-54-2) → 2-ethynyl-5-bromo-pyridine (111770-86-6)

Guidance literature:

With potassium carbonate; In methanol; acetonitrile; at 40 ℃; chemoselective reaction;

DOI:10.1016/j.catcom.2013.12.029

upstream raw materials:

3-bromo-6-(trimethylsilylethynyl)pyridine

2-iodo-5-bromopyridine

trimethylsilylacetylene

2-(tert-butyldimethylsilylethynyl)-5-bromopyridine

Downstream raw materials:

5-bromo-2-{4-[2-(4-methyl-piperidin-1-yl)-ethoxy]-phenylethynyl}-pyridine

chromium⁽⁰⁾ hexacarbonyl

tungsten hexacarbonyl

η5-cyclopentadienyl(2-(5-bromopyridyl)ethynyl)(triphenylphosphane)nickel(II)