2-Bromonicotinonitrile

Base Information

• Chemical Name: 2-Bromonicotinonitrile
• CAS No.: 20577-26-8
• Molecular Formula: C6H3BrN2
• Molecular Weight: 183.007
• Hs Code.: 2933399090
• European Community (EC) Number: 854-061-0
• DSSTox Substance ID: DTXSID90355753
• Wikidata: Q72448413
• Mol file: 20577-26-8.mol

Synonyms:2-Bromonicotinonitrile;20577-26-8;2-BROMO-3-CYANOPYRIDINE;2-bromopyridine-3-carbonitrile;2-Bromo-nicotinonitrile;3-Pyridinecarbonitrile, 2-bromo-;MFCD00234140;SCHEMBL571240;DTXSID90355753;QIPXEPRGYVAQFI-UHFFFAOYSA-N;HMS1655P21;RB1121;2-BROMO-3-PYRIDINECARBONITRILE;AKOS000320220;AB05139;AM62693;CS-W004810;AC-25800;DS-10491;SY023829;FT-0649121;EN300-66595;A814714;AC-907/25004481;W-201793;F1957-0002

Chemical Property of 2-Bromonicotinonitrile

Chemical Property:

• Vapor Pressure: 0.00139mmHg at 25°C
• Melting Point: 105 °C
• Refractive Index: 1.611
• Boiling Point: 296.9 °C at 760 mmHg
• PKA: -2.66±0.10(Predicted)
• Flash Point: 133.4 °C
• PSA: 36.68000
• Density: 1.72 g/cm³
• LogP: 1.71578
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 181.94796
• Heavy Atom Count: 9
• Complexity: 137

Purity/Quality:

98% ^*data from raw suppliers

2-Bromo-3-cyanopyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(N=C1)Br)C#N

Technology Process of 2-Bromonicotinonitrile

There total 6 articles about 2-Bromonicotinonitrile 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%

pyrid-2-one-3-carbonitrile (20577-27-9,5657-63-6) → 2-bromonicotinonitrile (20577-26-8)

Guidance literature:

With phosphorus pentoxide; tetrabutylammomium bromide; In toluene; for 12h; Reflux;

DOI:10.1016/j.bmc.2015.05.005

Reference yield: 92.0%

2-chloro-3-pyridinecarbonitrile (6602-54-6) → 2-bromonicotinonitrile (20577-26-8)

Guidance literature:

With trimethylsilyl bromide; In propiononitrile; for 70h; Heating;

DOI:10.1016/j.tet.2012.05.122

Reference yield: 77.7%

3-cyanopyridine N-oxide (14906-64-0) → 2-bromonicotinonitrile (20577-26-8)

Guidance literature:

With Oxalyl bromide; triethylamine; at -55 ℃; for 0.5h; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.5b01057

upstream raw materials:

2-hydroxy-3-cyanopyridine

phosphorus pentaoxide

2-chloro-3-pyridinecarbonitrile

3-cyanopyridine N-oxide

Downstream raw materials:

ethyl 2-(3-cyanopyridin-2-yl)acetate

amino-3 thieno<2,3-c> pyridine carboxylathe d,ethyle-2

ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate

benzyl(cyano-3 pyridyl-2) sulfure

Refernces

• 1、 Kumpan, Katerina,Nathubhai, Amit,Zhang, Chenlu,Wood, Pauline J.,Lloyd, Matthew D.,Thompson, Andrew S.,Haikarainen, Teemu,Lehti?, Lari,Threadgill, Michael D.. "Structure-based design, synthesis and evaluation in vitro of arylnaphthyridinones, arylpyridopyrimidinones and their tetrahydro derivatives as inhibitors of the tankyrases". . p. 3013 - 3032. Retrieved 2015/08/03.
• 2、 Piron, Karel,Kenis, Sara,Verniest, Guido,Surmont, Riccardo,Thuring, Jan Willem,Ten Holte, Peter,Deroose, Frederik,De Kimpe, Norbert. "Synthesis of gem-difluorinated 1,6-naphthyridine-5,7-diones". scheme or table. p. 6941 - 6947. Retrieved 2012/08/29.