3-Phenylpyrazine-2-carbonitrile

Base Information

• Chemical Name: 3-Phenylpyrazine-2-carbonitrile
• CAS No.: 2882-16-8
• Molecular Formula: C11H7N3
• Molecular Weight: 181.19300
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40536611
• Nikkaji Number: J437.391J
• Wikidata: Q82411334
• Mol file: 2882-16-8.mol

Synonyms:3-phenylpyrazine-2-carbonitrile;2882-16-8;3-Phenyl-pyrazine-2-carbonitrile;2-Pyrazinecarbonitrile, 3-phenyl-;2-Cyano-3-phenylpyrazine;SCHEMBL10427642;DTXSID40536611;AMY29052;CAA88216;MFCD10703576;AKOS006303691;AS-5599;CS-0450626;EN300-239963;F2167-2358

Chemical Property of 3-Phenylpyrazine-2-carbonitrile

Chemical Property:

• PSA: 49.57000
• LogP: 2.01528
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 181.063997236
• Heavy Atom Count: 14
• Complexity: 224

Purity/Quality:

97% ^*data from raw suppliers

3-Phenyl-pyrazine-2-carbonitrile 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=NC=CN=C2C#N
• Uses: 3-Phenylpyrazine-2-carbonitrile is used as a reactant in the silver-catalyzed Minisci reactions using Selectfluor as a mild oxidant.

Technology Process of 3-Phenylpyrazine-2-carbonitrile

There total 6 articles about 3-Phenylpyrazine-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: 66.0%

trimethylsilyl cyanide (7677-24-9) + 2-phenylpyrazine (29460-97-7) → 3-phenylpyrazine-2-carbonitrile (2882-16-8) + 5-Phenyl-2-pyrazinecarbonitrile (90687-96-0) + 6-Phenyl-2-pyrazinecarbonitrile (90701-04-5)

Guidance literature:

2-phenylpyrazine; With trifluoromethylsulfonic anhydride; In chloroform; at 20 ℃; for 1h; Inert atmosphere; Sealed tube;

trimethylsilyl cyanide; In chloroform; at 60 ℃; for 3h; Inert atmosphere; Sealed tube;

With 4-methyl-morpholine; In chloroform; at 60 ℃; for 17h; Overall yield = 80 %; Inert atmosphere; Sealed tube;

DOI:10.1002/chem.201703931

Reference yield: 62.0%

triphenylbismuthane (603-33-8) + 2-chloro-3-cyanopyrazine (55557-52-3) → 3-phenylpyrazine-2-carbonitrile (2882-16-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In N,N-dimethyl-formamide; at 130 ℃; Inert atmosphere; Sealed tube;

DOI:10.1002/ejoc.201300850

Reference yield: 17.0%

2-pyrazine carbonitrile (19847-12-2) + phenylboronic acid (98-80-6) → 3-phenylpyrazine-2-carbonitrile (2882-16-8) + 5-Phenyl-2-pyrazinecarbonitrile (90687-96-0) + 6-Phenyl-2-pyrazinecarbonitrile (90701-04-5)

Guidance literature:

2-pyrazine carbonitrile; phenylboronic acid; With Selectfluor; trifluoroacetic acid; In dichloromethane; water; at 20 ℃; for 0.0166667h;

With silver nitrate; In dichloromethane; water; at 50 ℃;

DOI:10.1021/acs.orglett.7b02706

upstream raw materials:

2-bromo-3-phenylpyrazine

3-phenyl-2(1H)-pyrazinone

triphenylbismuthane

2-chloro-3-cyanopyrazine

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