3-Pyridylmalononitrile

Base Information

• Chemical Name: 3-Pyridylmalononitrile
• CAS No.: 25230-06-2
• Molecular Formula: C₈H₅N₃
• Molecular Weight: 143.148
• DSSTox Substance ID: DTXSID40556455
• Wikidata: Q82438010
• Mol file: 25230-06-2.mol

Synonyms:3-Pyridylmalononitrile;25230-06-2;2-pyridin-3-ylpropanedinitrile;2-(3-pyridinyl)malononitrile;(Pyridin-3-yl)propanedinitrile;SCHEMBL7021489;2-pyridin-3-yl-propanedinitrile;DTXSID40556455;AKOS006276678

Chemical Property of 3-Pyridylmalononitrile

Chemical Property:

• PSA: 60.47000
• LogP: 1.21236
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 143.048347172
• Heavy Atom Count: 11
• Complexity: 200

Purity/Quality:

97% ^*data from raw suppliers

2-(3-pyridinyl)-Propanedinitrile 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 3-Pyridylmalononitrile

There total 3 articles about 3-Pyridylmalononitrile 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: 56.0%

3-pyridinylacetonitrile (6443-85-2) + 2-chlorobenzylthiocyanate (2082-66-8) → 3-Pyridylmalononitrile (25230-06-2)

Guidance literature:

With lithium diisopropyl amide; In benzene; at 5 ℃; for 1h;

DOI:10.1021/jo00164a030

Reference yield:

3-Bromopyridine (626-55-1,163928-56-1) + malononitrile (109-77-3) → 3-Pyridylmalononitrile (25230-06-2)

Guidance literature:

With potassium tert-butylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Yield given. Multistep reaction; 1.) DME, r.t., 10 min ; 2.) reflux, 2 h;

Reference yield:

3-iodopyridine (1120-90-7) + malononitrile (109-77-3) → 3-Pyridylmalononitrile (25230-06-2)

Guidance literature:

With sodium hydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Yield given. Multistep reaction; 1.) DME, r.t., 10 min ; 2.) reflux, 1.5 h;

upstream raw materials:

3-Bromopyridine

malononitrile

3-iodopyridine

3-pyridinylacetonitrile

Downstream raw materials:

[6-(5-phenyl-[1,2]dithiol-3-ylidene)-6H-pyridin-3-ylidene]-malononitrile

[6-(4-phenyl-[1,3]dithiol-2-ylidene)-6H-pyridin-3-ylidene]-malononitrile

Refernces

• 1、 Sakamoto, Takao,Katoh, Eisaku,Kondo, Yoshinori,Yamanaka, Hiroshi. "Cross-Coupling of N-Heteroaryl Halides with Active Methylene Compounds in the Presence of Tetrakis(triphenylphosphine)palladium". . p. 1664 - 1668. Retrieved 2007/10/02.