Benzoylacetonitrile

Base Information

• Chemical Name: Benzoylacetonitrile
• CAS No.: 614-16-4
• Deprecated CAS: 151887-87-5
• Molecular Formula: C9H7NO
• Molecular Weight: 145.161
• Hs Code.: 29269090
• European Community (EC) Number: 210-369-1
• NSC Number: 4713
• UNII: AFI9JB57H3
• DSSTox Substance ID: DTXSID7060629
• Nikkaji Number: J7.023H
• Wikidata: Q27122832
• Metabolomics Workbench ID: 57927
• ChEMBL ID: CHEMBL3251047
• Mol file: 614-16-4.mol

Synonyms:3-O-3-phenylpropanenitrile;3-oxo-3-phenylpropanenitrile

Chemical Property of Benzoylacetonitrile

Chemical Property:

• Appearance/Colour: Light yellow to yellow-brown crystalline powder
• Vapor Pressure: 0.00105mmHg at 25°C
• Melting Point: 78-82 °C
• Refractive Index: 1.536
• Boiling Point: 301.5 °C at 760 mmHg
• PKA: 7.78±0.10(Predicted)
• Flash Point: 132.9 °C
• PSA: 40.86000
• Density: 1.109 g/cm³
• LogP: 1.78298
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: slightly soluble
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 145.052763847
• Heavy Atom Count: 11
• Complexity: 183

Purity/Quality:

99% ^*data from raw suppliers

3-Oxo-3-phenylpropanenitrile 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-36/37/39-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)CC#N
• Uses: Benzoylacetonitrile can be used as a building block for the preparation of 4H-pyrans, 2-pyridones, furans and carbocyclics Benzoylacetonitrile is used to produce 2-benzoyl-3-furan-2-yl-acrylonitrile. It is also used in the synthesis of substituted naphtho[1,8-bc]pyrans and as building block in the preparation of 4H-pyrans, 2-pyridones, furans and carbocyclics. It is an active methylene compound, useful in heterocyclic synthesis, e.g. polyfunctional pyridines and pyrimidines.

Technology Process of Benzoylacetonitrile

There total 152 articles about Benzoylacetonitrile 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: 100.0%

benzoic acid methyl ester (93-58-3,5705-52-2,80226-58-0) + acetonitrile (75-05-8,26809-02-9) → Benzoylacetonitrile (614-16-4)

Guidance literature:

acetonitrile; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

benzoic acid methyl ester; In tetrahydrofuran; hexane; at -78 - -45 ℃; for 3h;

Reference yield: 98.0%

malononitrile (109-77-3) + phenylboronic acid (98-80-6) → Benzoylacetonitrile (614-16-4)

Guidance literature:

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

DOI:10.1021/acs.joc.0c02388

Reference yield: 93.0%

acetonitrile (75-05-8,26809-02-9) + benzyl alcohol (100-51-6,185532-71-2) → Benzoylacetonitrile (614-16-4)

Guidance literature:

With potassium hydroxide; In N,N-dimethyl-formamide; at 60 ℃; for 5h;

upstream raw materials:

5-phenylisoxazole

sodium ethanolate

5-phenyl-3-isoxazolecarboxylic acid

3-amino-3-phenylacrylonitrile

Downstream raw materials:

2-(1,1-dioxo-1H-1λ⁶-benzo[d]isothiazol-3-yl)-5-phenyl-2H-pyrazol-3-ylamine

(E)-2-benzoyl-3-(furan-2-yl)acrylonitrile

(Z)-2-Benzoyl-3-(5-bromo-furan-2-yl)-acrylonitrile

2-Cyano-2-(1,2-dihydroquinolin-2-ylidene)-1-phenylethanone

Refernces

• 1、 Sato. "-". . p. 2524. Retrieved 1968.
• 2、 Martins, Nayara Silva,ángel, Alix Y. Bastidas,Anghinoni, Jo?o M.,Lenard?o, Eder J.,Barcellos, Thiago,Alberto, Eduardo E.. "From Stoichiometric Reagents to Catalytic Partners: Selenonium Salts as Alkylating Agents for Nucleophilic Displacement Reactions in Water". supporting information. p. 87 - 93. Retrieved 2021/11/03.
• 3、 Hassan, Ghaneya S.,Georgey, Hanan H.,Mohammed, Esraa Z.,George, Riham F.,Mahmoud, Walaa R.,Omar, Farghaly A.. "Mechanistic selectivity investigation and 2D-QSAR study of some new antiproliferative pyrazoles and pyrazolopyridines as potential CDK2 inhibitors". . . Retrieved 2021/04/02.