2-Naphthalenemalononitrile

Base Information

• Chemical Name: 2-Naphthalenemalononitrile
• CAS No.: 32122-61-5
• Molecular Formula: C13H8N2
• Molecular Weight: 192.21600
• DSSTox Substance ID: DTXSID60536158
• Nikkaji Number: J565.179D
• Wikidata: Q82410735
• Mol file: 32122-61-5.mol

Synonyms:2-Naphthalenemalononitrile;32122-61-5;2-naphthalen-2-ylpropanedinitrile;SCHEMBL11323036;DTXSID60536158;(Naphthalen-2-yl)propanedinitrile

Chemical Property of 2-Naphthalenemalononitrile

Chemical Property:

• Melting Point: 172 °C
• Boiling Point: 372.7±22.0 °C(Predicted)
• PSA: 47.58000
• Density: 1.198±0.06 g/cm3(Predicted)
• LogP: 2.97056
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 192.068748264
• Heavy Atom Count: 15
• Complexity: 300

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C=C(C=CC2=C1)C(C#N)C#N

Technology Process of 2-Naphthalenemalononitrile

There total 4 articles about 2-Naphthalenemalononitrile 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: 86.0%

2-iodonaphthalene (612-55-5) + malononitrile (109-77-3) → 2-(naphthalen-6-yl)malononitrile (32122-61-5)

Guidance literature:

With sodium hydride; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; for 4h; Heating;

DOI:10.1039/c39840000932

Reference yield: 52.0%

2-bromonaphthalene (580-13-2) + malononitrile (109-77-3) → 2-(naphthalen-6-yl)malononitrile (32122-61-5)

Guidance literature:

malononitrile; With sodium hydride; In tetrahydrofuran; Inert atmosphere;

2-bromonaphthalene; With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 1,3,5,7-tetramethyl-2,4,8-trioxa-6-isobutyl-6-phosphaadamantane; In tetrahydrofuran; at 60 ℃; Inert atmosphere;

DOI:10.1021/ol202565j

Reference yield:

(3aS,9bS)-3a,9b-Dihydro-naphtho[1,2-c]furan-1,1,3,3-tetracarbonitrile → 2-(naphthalen-6-yl)malononitrile (32122-61-5)

Guidance literature:

With pyridine;

DOI:10.1016/S0040-4020(01)82528-X

upstream raw materials:

2-iodonaphthalene

malononitrile

2-bromonaphthalene

Refernces

• 1、 Edjoc, Racquel K.,Mills, L. Reginald,Rousseaux, Sophie A. L.. "Design of an Electron-Withdrawing Benzonitrile Ligand for Ni-Catalyzed Cross-Coupling Involving Tertiary Nucleophiles". supporting information. p. 10422 - 10428. Retrieved 2021/07/26.
• 2、 Uno, Mitsunari,Seto, Koji,Takahashi, Shigetoshi. "A New Method of Synthesis of Arylmalononitriles catalysed by a Palladium Complex". . p. 932 - 933. Retrieved 2007/10/02.