2-Naphthoylacetonitrile

Base Information

• Chemical Name: 2-Naphthoylacetonitrile
• CAS No.: 613-57-0
• Molecular Formula: C13H9NO
• Molecular Weight: 195.221
• NSC Number: 9851
• DSSTox Substance ID: DTXSID60278748
• Nikkaji Number: J95.550G
• Wikidata: Q82010848
• Mol file: 613-57-0.mol

Synonyms:2-Naphthoylacetonitrile;613-57-0;3-(naphthalen-2-yl)-3-oxopropanenitrile;3-naphthalen-2-yl-3-oxopropanenitrile;MFCD02260808;3-(naphthalen-2-yl)-3-oxopropionitrile;3-(2-naphthyl)-3-oxopropanenitrile;NSC9851;SCHEMBL4160389;DTXSID60278748;beta-oxo-2-naphthalenepropionitrile;NSC-9851;3-Oxo-3-(2-naphthyl)propionitrile;AKOS000179958;SY092780;A8509;CS-0315765;FT-0604168;F72224

Chemical Property of 2-Naphthoylacetonitrile

Chemical Property:

• Vapor Pressure: 9.05E-07mmHg at 25°C
• Melting Point: 127.6-128.2 °C
• Refractive Index: 1.629
• Boiling Point: 405 °C at 760 mmHg
• PKA: 7.78±0.30(Predicted)
• Flash Point: 198.7 °C
• PSA: 40.86000
• Density: 1.183 g/cm³
• LogP: 2.93618
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 195.068413911
• Heavy Atom Count: 15
• Complexity: 288

Purity/Quality:

98%min ^*data from raw suppliers

2-Naphthoylacetonitrile 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-Naphthoylacetonitrile

There total 10 articles about 2-Naphthoylacetonitrile 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: 93.0%

naphthalene-2-boronic acid (32316-92-0) + malononitrile (109-77-3) → 3-(naphthalen-2-yl)-3-oxopropanenitrile (613-57-0)

Guidance literature:

With 4,4'-dimethyl-2,2'-bipyridines; palladium(II) acetylacetonate; toluene-4-sulfonic acid; In water; toluene; at 80 ℃; for 24h; Schlenk technique;

DOI:10.1021/acs.joc.0c02388

Reference yield: 85.0%

2-Naphthalenemethanol (1592-38-7) + acetonitrile (75-05-8,26809-02-9) → 3-(naphthalen-2-yl)-3-oxopropanenitrile (613-57-0)

Guidance literature:

With oxygen; potassium hydroxide; copper dichloride; In N,N-dimethyl acetamide; at 20 ℃; for 12h; Green chemistry;

DOI:10.1021/ol403555n

Reference yield: 83.0%

2-trimethylsilylacetonitrile (18293-53-3) + 2-iodonaphthalene (612-55-5) + molybdenum hexacarbonyl (13939-06-5,199620-15-0) → 3-(naphthalen-2-yl)-3-oxopropanenitrile (613-57-0)

Guidance literature:

With copper (II)-fluoride; bis-triphenylphosphine-palladium(II) chloride; In acetonitrile; at 80 ℃; for 16h;

DOI:10.1055/s-0032-1316760

upstream raw materials:

ethyl-2-naphthoate

acetonitrile

4-chlorophenyl acetate

3-hydroxy-3-(naphthalen-2-yl)propanenitrile

Refernces

• 1、 Liu, Chong,Yuan, Jing,Zhang, Zhenfeng,Gridnev, Ilya D.,Zhang, Wanbin. "Asymmetric Hydroacylation Involving Alkene Isomerization for the Construction of C3-Chirogenic Center". supporting information. p. 8997 - 9002. Retrieved 2021/03/16.
• 2、 Sharma, Pawan K.,Kumar, Rajiv,Ram, Sita,Chandak, Navneet. "Deadly KCN and pricey metal free track for accessing β-ketonitriles employing mild reaction conditions". supporting information. p. 1847 - 1856. Retrieved 2021/04/26.