2-Benzoylbutanenitrile

Base Information

• Chemical Name: 2-Benzoylbutanenitrile
• CAS No.: 7391-31-3
• Molecular Formula: C11H11NO
• Molecular Weight: 173.214
• European Community (EC) Number: 838-778-6
• Nikkaji Number: J983.933J
• Mol file: 7391-31-3.mol

Synonyms:2-benzoylbutanenitrile;7391-31-3;MFCD12115815;AKOS009860093;EN300-366059;Z445223930

Chemical Property of 2-Benzoylbutanenitrile

Chemical Property:

• Boiling Point: 122 °C(Press: 5 Torr)
• PSA: 40.86000
• Density: 1.054±0.06 g/cm3(Predicted)
• LogP: 2.41908
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 173.084063974
• Heavy Atom Count: 13
• Complexity: 220

Purity/Quality:

95% ^*data from raw suppliers

2-benzoylbutanenitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-Benzoylbutanenitrile

There total 17 articles about 2-Benzoylbutanenitrile 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: 90.0%

(E)-1-phenyl-2-buten-1-one (35660-91-4,35845-66-0,495-41-0) + N-cyano-N-phenyl-p-toluenesulfonamide (55305-43-6) → 2-ethyl-3-oxo-3-phenylpropanenitrile (7391-31-3)

Guidance literature:

With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 40 ℃; for 12h; Inert atmosphere;

DOI:10.1002/anie.201605445

Reference yield: 90.0%

propyl cyanide (109-74-0) + benzoic acid ethyl ester (93-89-0,99341-95-4) → 2-ethyl-3-oxo-3-phenylpropanenitrile (7391-31-3)

Guidance literature:

benzoic acid ethyl ester; With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 0.166667h;

propyl cyanide; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jacs.0c13273

Reference yield: 86.0%

D-glucose (50-99-7) + Benzoylacetonitrile (614-16-4) → 2-ethyl-3-oxo-3-phenylpropanenitrile (7391-31-3)

Guidance literature:

With Saccharomyces cerevisiae Zeus whole cell; In aq. phosphate buffer; dimethyl sulfoxide; at 28 ℃; pH=7; Microbiological reaction;

DOI:10.1016/j.tetasy.2016.04.002

upstream raw materials:

4-ethyl-5-phenyl-isoxazole

benzoic acid ethyl ester

3-amino-2-ethyl-3-phenyl-acrylonitrile

2-bromobutyronitrile

Downstream raw materials:

(S)-3-hydroxy-3-phenylpropanenitrile

(R)-6-phenyl-1,3-oxazinan-2-one R-7a

(2S,3S)-2-(1-hydroxy-1-phenylmethyl)butanenitrile

2-(1-hydroxy-1-phenylmethyl)butanenitrile

Refernces

• 1、 Hale, Lillian V. A.,Sikes, N. Marianne,Szymczak, Nathaniel K.. "Reductive C?C Coupling from α,β-Unsaturated Nitriles by Intercepting Keteniminates". supporting information. p. 8531 - 8535. Retrieved 2019/05/21.
• 2、 Rimoldi, Isabella,Facchetti, Giorgio,Nava, Donatella,Contente, Martina Letizia,Gandolfi, Raffella. "Efficient methodology to produce a duloxetine precursor using whole cells of Rhodotorula rubra". . p. 389 - 396. Retrieved 2016/05/19.