4-Phenylbenzoylacetonitrile

Base Information

• Chemical Name: 4-Phenylbenzoylacetonitrile
• CAS No.: 78443-35-3
• Molecular Formula: C15H11NO
• Molecular Weight: 221.258
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID00506890
• Wikidata: Q82362854
• Mol file: 78443-35-3.mol

Synonyms:78443-35-3;4-PHENYLBENZOYLACETONITRILE;3-[1,1'-biphenyl]-4-yl-3-oxopropanenitrile;3-oxo-3-(4-phenylphenyl)propanenitrile;3-([1,1'-Biphenyl]-4-yl)-3-oxopropanenitrile;3-{[1,1'-biphenyl]-4-yl}-3-oxopropanenitrile;MFCD02260810;3-Biphenyl-4-yl-3-oxo-propanenitrile;SCHEMBL3588115;DTXSID00506890;BZAJCNCPXHAXBZ-UHFFFAOYSA-N;AKOS000368900;GC-0212;A9867;FT-0604201;J-510396

Chemical Property of 4-Phenylbenzoylacetonitrile

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 116-118 °C
• Refractive Index: 1.582
• Boiling Point: 418.129 °C at 760 mmHg
• Flash Point: 206.677 °C
• PSA: 40.86000
• Density: 1.128 g/cm³
• LogP: 3.44998
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 221.084063974
• Heavy Atom Count: 17
• Complexity: 300

Purity/Quality:

98%min ^*data from raw suppliers

4-phenylbenzoylacetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC=C(C=C2)C(=O)CC#N

Technology Process of 4-Phenylbenzoylacetonitrile

There total 16 articles about 4-Phenylbenzoylacetonitrile 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: 91.0%

N-methoxy-N-methyl-[1,1'-biphenyl]-4-carboxamide (101335-77-7) + acetonitrile (75-05-8,26809-02-9) → 3-(<1,1'-biphenyl>-4-yl)-3-oxopropionitrile (78443-35-3)

Guidance literature:

acetonitrile; With methyllithium; lithium bromide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.5h; Inert atmosphere;

N-methoxy-N-methyl-[1,1'-biphenyl]-4-carboxamide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1.5h; Inert atmosphere;

DOI:10.1039/c4ob02398f

Reference yield: 80.0%

4-biphenylboronic acid (5122-94-1) + malononitrile (109-77-3) → 3-(<1,1'-biphenyl>-4-yl)-3-oxopropionitrile (78443-35-3)

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: 80.0%

(E)-3-Biphenyl-4-yl-3-chloro-acrylonitrile (60131-48-8) → 3-(<1,1'-biphenyl>-4-yl)-3-oxopropionitrile (78443-35-3)

Guidance literature:

With sodium hydroxide; In water; dimethyl sulfoxide; at 25 ℃;

DOI:10.1080/00397911.2021.1910846

upstream raw materials:

4-(chloroacetyl)biphenyl

sodium cyanide

potassium cyanide

5-(<1,1'-biphenyl>-4-yl)-isoxazole

Downstream raw materials:

3,5-dicyano-3-cyanomethyl-2,4,6-tri(4-phenylphenyl)-2H-pyran

(Z)-2-(Biphenyl-4-carbonyl)-3-(4-nitro-phenyl)-acrylonitrile

N-[4-((Z)-3-Biphenyl-4-yl-2-cyano-3-oxo-propenyl)-phenyl]-acetamide

(Z)-2-(Biphenyl-4-carbonyl)-3-(4-iodo-phenyl)-acrylonitrile

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、 -. "Method for synthesizing beta-ketonitrile and derivatives thereof". Paragraph 0061-0065. . Retrieved 2021/04/21.