1-Methylnaphthalene-2-carbonitrile

Base Information

• Chemical Name: 1-Methylnaphthalene-2-carbonitrile
• CAS No.: 20176-06-1
• Molecular Formula: C12H9N
• Molecular Weight: 167.20656
• DSSTox Substance ID: DTXSID50516681
• Wikidata: Q82378208
• Mol file: 20176-06-1.mol

Synonyms:20176-06-1;1-methylnaphthalene-2-carbonitrile;1-Methyl-2-naphthonitrile;SCHEMBL5950664;DTXSID50516681;FT-0739343

Chemical Property of 1-Methylnaphthalene-2-carbonitrile

Chemical Property:

• PSA: 23.79000
• LogP: 3.01988
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 167.073499291
• Heavy Atom Count: 13
• Complexity: 225

Purity/Quality:

98% ^*data from raw suppliers

2-Cyano-1-methylnaphthalene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C=CC2=CC=CC=C12)C#N

Technology Process of 1-Methylnaphthalene-2-carbonitrile

There total 11 articles about 1-Methylnaphthalene-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:

benzyl>dimethylamine (41839-73-0) → 1-methyl-2-cyanonaphthalene (20176-06-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) n-BuLi / 1.) THF, 0 deg C, 12 h, 2.) 0 deg C, 1 h; room temperature, 2 h

2: 65 percent / acetonitrile / 1.) room temperature, 1 h, 2.) reflux, 1 h

3: 1.) t-Bu₄NF / 2.) palladium charcoal / 1.) MeCN, room temperature, 1 h, 2.) tetralin, reflux, 26 h

With n-butyllithium; tetra(tert-butyl)-ammonium fluoride; palladium on activated charcoal; In acetonitrile;

DOI:10.1021/ja00390a036

Reference yield:

benzyl>dimethylamine (83781-51-5) → 1-methyl-2-cyanonaphthalene (20176-06-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / acetonitrile / 1.) room temperature, 1 h, 2.) reflux, 1 h

2: 1.) t-Bu₄NF / 2.) palladium charcoal / 1.) MeCN, room temperature, 1 h, 2.) tetralin, reflux, 26 h

With tetra(tert-butyl)-ammonium fluoride; palladium on activated charcoal; In acetonitrile;

DOI:10.1021/ja00390a036

Reference yield:

N,N-dimethyl(2-methylbenzyl)amine (4525-48-8) → 1-methyl-2-cyanonaphthalene (20176-06-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-BuLi, 2.) Et₃N / 1.) Et₂O, room temperatutre, 22 h, 2.) room temperature, 4 h

2: 1.) n-BuLi / 1.) THF, 0 deg C, 12 h, 2.) 0 deg C, 1 h; room temperature, 2 h

3: 65 percent / acetonitrile / 1.) room temperature, 1 h, 2.) reflux, 1 h

4: 1.) t-Bu₄NF / 2.) palladium charcoal / 1.) MeCN, room temperature, 1 h, 2.) tetralin, reflux, 26 h

With n-butyllithium; tetra(tert-butyl)-ammonium fluoride; triethylamine; palladium on activated charcoal; In acetonitrile;

DOI:10.1021/ja00390a036

upstream raw materials:

1-methyl-2-cyano-1,2,3,4-tetrahydronaphthalene

acrylonitrile

ethanedinitrile

(1-naphthylmethyl)magnesium chloride

Refernces

• 1、 Ito,Nakatsuka,Saegusa. "Syntheses of polycyclic ring systems based on the new generation of o-quinodimethanes". . p. 7609 - 7622. Retrieved 2007/10/13.