5-Phenylpyridine-3-carbonitrile

Base Information

• Chemical Name: 5-Phenylpyridine-3-carbonitrile
• CAS No.: 10177-11-4
• Molecular Formula: C12H8 N2
• Molecular Weight: 180.21
• Hs Code.: 2933399090
• NSC Number: 167779
• DSSTox Substance ID: DTXSID60304859
• Nikkaji Number: J992.545G
• Wikidata: Q82051128
• Mol file: 10177-11-4.mol

Synonyms:5-Phenylnicotinonitrile;10177-11-4;5-phenylpyridine-3-carbonitrile;3-CYANO-5-PHENYLPYRIDINE;NSC167779;SCHEMBL2979806;5-phenyl-3-pyridinecarbonitrile;DTXSID60304859;AKOS006307839;NSC 167779;NSC-167779;FT-0763305;EN300-239937;A800446;J-517927;F2167-2457

Chemical Property of 5-Phenylpyridine-3-carbonitrile

Chemical Property:

• Vapor Pressure: 8.89E-05mmHg at 25°C
• Boiling Point: 339.9°Cat760mmHg
• Flash Point: 119.5°C
• PSA: 36.68000
• Density: 1.17g/cm³
• LogP: 2.62028
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 180.068748264
• Heavy Atom Count: 14
• Complexity: 222

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Phenylnicotinonitrile ^*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=CN=CC(=C2)C#N

Technology Process of 5-Phenylpyridine-3-carbonitrile

There total 4 articles about 5-Phenylpyridine-3-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: 92.0%

5-bromopyridine-3-carbonitrile (35590-37-5) + phenylmagnesium chloride (100-59-4) → 5-phenylnicotinonitrile (10177-11-4)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride; In tetrahydrofuran; at 55 - 60 ℃;

DOI:10.1016/S0040-4039(98)01587-1

Reference yield: 62.0%

5-bromo-3-pyridinecarboxylic acid (20826-04-4) + phenylboronic acid (98-80-6) → 5-phenylnicotinonitrile (10177-11-4)

Guidance literature:

5-bromo-3-pyridinecarboxylic acid; With resin-bound amine; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

phenylboronic acid; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,2-dimethoxyethane; for 48h; Heating;

With pyridine; trifluoroacetic anhydride; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1016/S0040-4039(00)01988-2

Reference yield: 58.0%

bromobenzene (108-86-1,52753-63-6) + 3-cyanopyridine-5-boronic acid pinacol ester (402718-29-0) → 5-phenylnicotinonitrile (10177-11-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,4-dioxane; ethanol; water; at 85 ℃; for 19h; Inert atmosphere;

DOI:10.1021/jacs.7b11710

upstream raw materials:

5-bromopyridine-3-carbonitrile

phenylmagnesium chloride

5-bromo-3-pyridinecarboxylic acid

phenylboronic acid

Downstream raw materials:

chlorhydrate de l'acide phenyl-5 nipecotique

phenyl-5 nipecotate d'ethyle

5-phenylnicotinic acid ethyl ester

Refernces

• 1、 Miller, Joseph A.,Farrell, Robert P.. "Synthesis of functionally substituted unsymmetrical biaryls via a novel double metal catalyzed coupling reaction". . p. 7275 - 7278. Retrieved 1998.
• 2、 Koniarczyk, J. Luke,Hesk, David,Overgard, Alix,Davies, Ian W.,McNally, Andrew. "A General Strategy for Site-Selective Incorporation of Deuterium and Tritium into Pyridines, Diazines, and Pharmaceuticals". supporting information. p. 1990 - 1993. Retrieved 2018/02/19.