2-(2-Cyanophenyl)acetophenone

Base Information

• Chemical Name: 2-(2-Cyanophenyl)acetophenone
• CAS No.: 10517-64-3
• Molecular Formula: C15H11NO
• Molecular Weight: 221.258
• Hs Code.: 2926909090
• NSC Number: 100685
• DSSTox Substance ID: DTXSID90295226
• Nikkaji Number: J1.207.364J
• Wikidata: Q82035027
• Mol file: 10517-64-3.mol

Synonyms:2-(2-CYANOPHENYL)ACETOPHENONE;10517-64-3;2-phenacylbenzonitrile;2-(2-oxo-2-phenylethyl)benzonitrile;MFCD00029561;NSC100685;NCIOpen2_006939;SCHEMBL1515908;DTXSID90295226;AKOS016019525;NSC-100685;FT-0720324

Chemical Property of 2-(2-Cyanophenyl)acetophenone

Chemical Property:

• Vapor Pressure: 5.14E-06mmHg at 25°C
• Melting Point: 109-111 °C(Solv: ethanol (64-17-5))
• Refractive Index: 1.604
• Boiling Point: 381.3 °C at 760 mmHg
• Flash Point: 184.4 °C
• PSA: 40.86000
• Density: 1.16 g/cm³
• LogP: 2.98368
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 221.084063974
• Heavy Atom Count: 17
• Complexity: 308

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-(2-Cyanophenyl)acetophenone 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-(2-Cyanophenyl)acetophenone

There total 10 articles about 2-(2-Cyanophenyl)acetophenone 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-Methylbenzonitrile (529-19-1) + N-methoxy-N-methylbenzamide (6919-61-5) → 1-(2-Cyanophenyl)-1-phenyl-1-ethanone (10517-64-3)

Guidance literature:

2-Methylbenzonitrile; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

N-methoxy-N-methylbenzamide; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

DOI:10.1080/00304949909355729

Reference yield: 70.0%

bicyclo[4.2.0]octa-1,3,5-trien-7-one O-(2,4-dinitrophenyl)oxime + benzaldehyde (100-52-7) → 1-(2-Cyanophenyl)-1-phenyl-1-ethanone (10517-64-3)

Guidance literature:

With 3-(2,6-diisopropylphenyl)-4,5,6,7-tetrahydrobenzo[d]thiazol-3-ium perchlorate; caesium carbonate; In 1,2-dichloro-ethane; at 60 ℃; for 24h; Inert atmosphere; Sealed tube; Green chemistry;

DOI:10.1021/acs.orglett.0c04248

Reference yield: 62.0%

benzoic acid methyl ester (93-58-3,5705-52-2,80226-58-0) + 2-Methylbenzonitrile (529-19-1) → 1-(2-Cyanophenyl)-1-phenyl-1-ethanone (10517-64-3)

Guidance literature:

With sodium hydride; In methanol; 1,2-dimethoxyethane; mineral oil; at 60 ℃; for 10.25h; Inert atmosphere;

DOI:10.3762/bjoc.17.186

upstream raw materials:

benzoic acid methyl ester

2-Methylbenzonitrile

α,α'-dichloro-bibenzyl-2-carboxylic acid amide

benzoic acid ethyl ester

Downstream raw materials:

2-<(2-phenyl-1,3-dioxolan-2-yl)methyl>benzonitrile

4-hydroxy-3-phenylisoquinoline

3-phenylisoquinoline

2-(4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrimidin-5-yl)benzonitrile

Refernces

• 1、 Bunce, Richard A.,Johnson, Lara B.. "Acylation and alkylation of 2-and 4-methylbenzonitrile". . p. 407 - 412. Retrieved 1999.
• 2、 Yang, Hai-Bin,Wan, Dan-Hong. "C?C bond acylation of oxime ethers via NHC catalysis". supporting information. p. 1049 - 1053. Retrieved 2021/02/01.