4-(4-Chlorophenyl)-4-oxo-2-phenylbutanenitrile

Base Information

• Chemical Name: 4-(4-Chlorophenyl)-4-oxo-2-phenylbutanenitrile
• CAS No.: 6273-45-6
• Molecular Formula: C16H12ClNO
• Molecular Weight: 269.7256
• NSC Number: 32903
• DSSTox Substance ID: DTXSID90283683
• Nikkaji Number: J2.427.370I
• ChEMBL ID: CHEMBL1725611
• Mol file: 6273-45-6.mol

Synonyms:4-(4-chlorophenyl)-4-oxo-2-phenylbutanenitrile;6273-45-6;MLS002607832;NSC32903;SCHEMBL6203933;CHEMBL1725611;DTXSID90283683;HMS3078A22;NSC-32903;AKOS005098209;7J-511S;SMR001526599

Chemical Property of 4-(4-Chlorophenyl)-4-oxo-2-phenylbutanenitrile

Chemical Property:

• Vapor Pressure: 7.26E-09mmHg at 25°C
• Boiling Point: 466.1°C at 760 mmHg
• Flash Point: 235.7°C
• PSA: 40.86000
• Density: 1.221g/cm³
• LogP: 4.22018
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 269.0607417
• Heavy Atom Count: 19
• Complexity: 345

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(CC(=O)C2=CC=C(C=C2)Cl)C#N
• Uses: 4-Chloro-γ-oxo-α-phenylbenzenebutanenitrile is an intermediate in the synthesis of Fenbuconazole-lactone B R-9130 (T767730), a metabolite of Fenbuconazole (F246800) which is a conazole based fungicide used as a spray for the control of leaf spot, yellow and brown rust, powdery mildew and net blotch on wheat and barley and apple scab, pear scab and apple powdery mildew on apples and pears.

Technology Process of 4-(4-Chlorophenyl)-4-oxo-2-phenylbutanenitrile

There total 9 articles about 4-(4-Chlorophenyl)-4-oxo-2-phenylbutanenitrile 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: 92.0%

4'-chlorochalcone (956-02-5) + malononitrile (109-77-3) → 4-(4-chlorophenyl)-4-oxo-2-phenylbutanenitrile (6273-45-6)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1039/c2cc35528k

Reference yield: 90.0%

ethyl 2-cyanoacetate (105-56-6) + 4'-chlorochalcone (956-02-5) → 4-(4-chlorophenyl)-4-oxo-2-phenylbutanenitrile (6273-45-6)

Guidance literature:

With potassium hydroxide; In N,N-dimethyl-formamide; at 20 ℃; for 8h;

DOI:10.1002/cjoc.201600860

Reference yield: 85.0%

benzoyl cyanide (613-90-1) + 4'-chlorochalcone (956-02-5) → 4-(4-chlorophenyl)-4-oxo-2-phenylbutanenitrile (6273-45-6)

Guidance literature:

With potassium hydroxide; In water; acetonitrile; at 40 ℃; for 18h;

DOI:10.1055/s-0032-1317179

upstream raw materials:

potassium cyanide

4'-chlorochalcone

2-hydroxy-2-methylpropanenitrile

trimethylsilyl cyanide

Downstream raw materials:

methyl 4-oxo-4-(4-chlorophenyl)-2-phenyl-butanoate

4-(4-chloro-phenyl)-3-hydroxy-4-oxo-2-phenyl-butyric acid

3-bromo-4-(4-chloro-phenyl)-4-oxo-2-phenyl-butyric acid

Refernces

• 1、 Li, Zheng,Yin, Junjun. "Conjugate Hydrocyanation of Chalcone Derivatives Using Ethyl Cyanoacetate as an Organic Cyanide Source". . p. 1179 - 1184. Retrieved 2017/07/24.
• 2、 Li, Zheng,Liu, Chenhui,Zhang, Yupeng,Li, Rongzhi,Ma, Ben,Yang, Jingya. "Conjugate hydrocyanation of aromatic enones using potassium hexacyanoferrate(II) as an eco-friendly cyanide source". supporting information. p. 2567 - 2571. Retrieved 2012/11/13.