6-Pyrrolidin-1-ylnicotinonitrile

Base Information

• Chemical Name: 6-Pyrrolidin-1-ylnicotinonitrile
• CAS No.: 90839-82-0
• Molecular Formula: C₁₀H₁₁N₃
• Molecular Weight: 173.217
• Hs Code.: 2933990090
• European Community (EC) Number: 839-373-7
• DSSTox Substance ID: DTXSID90437442
• Nikkaji Number: J3.049.867D
• Wikidata: Q82252931
• Mol file: 90839-82-0.mol

Synonyms:6-pyrrolidin-1-ylnicotinonitrile;90839-82-0;6-(Pyrrolidin-1-yl)nicotinonitrile;6-(pyrrolidin-1-yl)pyridine-3-carbonitrile;6-pyrrolidin-1-ylpyridine-3-carbonitrile;6-Pyrrolidin-1-yl-nicotinonitrile;SCHEMBL3048925;DTXSID90437442;MFCD09863403;AKOS000198419;SB55306;TS-02380;2-(1-Pyrrolidinyl)pyridine-5-carbonitrile;FT-0728147;EN300-30741;Z219095946

Chemical Property of 6-Pyrrolidin-1-ylnicotinonitrile

Chemical Property:

• PSA: 39.92000
• LogP: 1.61848
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 173.095297364
• Heavy Atom Count: 13
• Complexity: 212

Purity/Quality:

95+% ^*data from raw suppliers

6-Pyrrolidin-1-ylnicotinonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(C1)C2=NC=C(C=C2)C#N

Technology Process of 6-Pyrrolidin-1-ylnicotinonitrile

There total 4 articles about 6-Pyrrolidin-1-ylnicotinonitrile 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: 98.0%

zinc(II) cyanide (557-21-1) + 5-bromo-2-(pyrrolidin-1-yl)pyridine (210963-93-2) → 2-(pyrrolidin-1-yl)-5-cyanopyridine (90839-82-0)

Guidance literature:

With C₁₂H₁₀N^(1-)*CH₃O₃S^(1-)*Pd⁽²⁺⁾*C₃₉H₃₂OP₂; In tetrahydrofuran; water; at 65 ℃; for 3h; Micellar solution;

DOI:10.1002/cctc.202001742

Reference yield: 92.0%

potassiumhexacyanoferrate(II) trihydrate + 5-bromo-2-(pyrrolidin-1-yl)pyridine (210963-93-2) → 2-(pyrrolidin-1-yl)-5-cyanopyridine (90839-82-0)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,8-diazabicyclo[5.4.0]undec-7-ene; In water; tert-butyl alcohol; at 85 ℃; for 4h; Inert atmosphere;

DOI:10.1039/c2cc17468e

Reference yield:

pyrrolidine (123-75-1) + Pyridine-2,5-dicarbonitrile (20730-07-8) → 2-(pyrrolidin-1-yl)-5-cyanopyridine (90839-82-0) + 5-Pyrrolidin-1-yl-pyridine-2-carbonitrile + [2,3']Bipyridinyl-5,6'-dicarbonitrile

Guidance literature:

In acetonitrile; for 4h; Yield given. Yields of byproduct given; Irradiation;

upstream raw materials:

pyrrolidine

Pyridine-2,5-dicarbonitrile

5-bromo-2-(pyrrolidin-1-yl)pyridine

zinc(II) cyanide

Refernces

• 1、 Zhang, Dengyou,Sun, Haifeng,Zhang, Lei,Zhou, Yu,Li, Chunpu,Jiang, Hualiang,Chen, Kaixian,Liu, Hong. "An expedient Pd/DBU mediated cyanation of aryl/heteroaryl bromides with K4[Fe(CN)6]". supporting information; experimental part. p. 2909 - 2911. Retrieved 2012/03/27.