4-Bromopyridine-2-carbonitrile

Base Information

• Chemical Name: 4-Bromopyridine-2-carbonitrile
• CAS No.: 62150-45-2
• Molecular Formula: C6H3BrN2
• Molecular Weight: 183.007
• Hs Code.: 2933399090
• European Community (EC) Number: 688-035-3
• DSSTox Substance ID: DTXSID40351205
• Wikidata: Q72511904
• ChEMBL ID: CHEMBL4563874
• Mol file: 62150-45-2.mol

Synonyms:4-bromopyridine-2-carbonitrile;62150-45-2;4-Bromo-2-cyanopyridine;4-bromopicolinonitrile;4-BROMO-PYRIDINE-2-CARBONITRILE;2-Pyridinecarbonitrile, 4-bromo-;MFCD04065805;4-BROMO-2-PYRIDINECARBONITRILE;4-Bromo-2-cyano-pyridine;SCHEMBL504885;CHEMBL4563874;DTXSID40351205;BCP27215;BBL102529;STL556332;AKOS000275960;AC-9582;CS-W019598;PB29307;PS-3946;SY015416;AM20061382;FT-0600164;VU0509242-1;A15705;EN300-102445;J-400564;F3099-7184

Chemical Property of 4-Bromopyridine-2-carbonitrile

Chemical Property:

• Appearance/Colour: off-solid
• Melting Point: 82-84 °C
• Refractive Index: 1.544
• Boiling Point: 265.312 °C at 760 mmHg
• PKA: -2.73±0.10(Predicted)
• Flash Point: 114.257 °C
• PSA: 36.68000
• Density: 1.726 g/cm³
• LogP: 1.71578
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• 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:

99% ^*data from raw suppliers

4-Bromopyridine-2-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN=C(C=C1Br)C#N
• Uses: 4-Bromopyridine-2-Carbonitrile is a useful synthetic intermediate.

Technology Process of 4-Bromopyridine-2-carbonitrile

There total 5 articles about 4-Bromopyridine-2-carbonitrile 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%

4-bromopyridine-1-oxide (14248-50-1) + trimethylsilyl cyanide (7677-24-9) → 4-bromo-2-cyanopyridine (62150-45-2)

Guidance literature:

With triethylamine; In acetonitrile; for 3.5h; Schlenk technique; Inert atmosphere; Reflux;

DOI:10.1016/j.bmc.2020.115610

Reference yield: 49.0%

4-bromopyridine-1-oxide (14248-50-1) → 4-bromo-2-cyanopyridine (62150-45-2)

Guidance literature:

Reference yield:

4-bromopyridin (1120-87-2) → 4-bromo-2-cyanopyridine (62150-45-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 3-chloro-benzenecarboperoxoic acid / diethyl ether / 8 h / 20 °C

2: triethylamine / 24 h / 95 °C

With triethylamine; 3-chloro-benzenecarboperoxoic acid; In diethyl ether;

DOI:10.1021/acs.inorgchem.5b01967

upstream raw materials:

4-bromopyridine-1-oxide

trimethylsilyl cyanide

4-bromopyridin

4-bromopyridine hydrochloride

Downstream raw materials:

4-trimethylsilanylethynyl-pyridine-2-carbonitrile

1-(4-bromopyridin-2-yl)methanamine

N-t-butoxycarbonyl-3-(2-cyano-4-pyridyl)-(S)-alanine benzyl ester

C₁₄H₁₁N₃O₂