2-(4-Chlorophenyl)-3-oxovaleronitrile

Base Information

• Chemical Name: 2-(4-Chlorophenyl)-3-oxovaleronitrile
• CAS No.: 55474-40-3
• Molecular Formula: C11H10 Cl N O
• Molecular Weight: 207.659
• European Community (EC) Number: 259-656-3
• UNII: T3A59YLW65
• DSSTox Substance ID: DTXSID20970817
• Nikkaji Number: J267.004F
• Mol file: 55474-40-3.mol

Synonyms:55474-40-3;2-(4-chlorophenyl)-3-oxopentanenitrile;2-(4-Chlorophenyl)-3-oxovaleronitrile;EINECS 259-656-3;T3A59YLW65;UNII-T3A59YLW65;C11H10ClNO;alpha-(4-Chlorophenyl)-alpha-propionylacetonitrile;|A-(4-Chlorophenyl)-|A-propionylacetonitrile;SCHEMBL4735057;DTXSID20970817;AKOS009353352;4-chloro-a-ethylcarbonylbenzeneacetonitrile;alpha-propionyl-p-chlorophenyl acetonitrile;?-(4-Chlorophenyl)-?-propionylacetonitrile;FT-0664915;PYRIMETHAMINE IMPURITY A [EP IMPURITY];4-Chloro-alpha-(1-oxopropyl)benzeneacetonitrile;VALERONITRILE, 2-(P-CHLOROPHENYL)-3-OXO-;alpha -(4-Chlorophenyl)- alpha -propionylacetonitrile;(2.XI.)-2-(4-CHLOROPHENYL)-3-OXOPENTANENITRILE;4-CHLORO-.ALPHA.-(1-OXOPROPYL)BENZENEACETONITRILE;BENZENEACETONITRILE, 4-CHLORO-.ALPHA.-(1-OXOPROPYL)-;4-Chloro-alpha-(1-oxopropyl)-benzeneacetonitrile;2-(p-Chlorophenyl)-3-oxo-valeronitrile

Chemical Property of 2-(4-Chlorophenyl)-3-oxovaleronitrile

Chemical Property:

• Vapor Pressure: 0.00197mmHg at 25°C
• Boiling Point: 291.2°C at 760 mmHg
• Flash Point: 129.9°C
• PSA: 40.86000
• Density: 1.186g/cm³
• LogP: 2.92628
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly, Sonicated), Methanol (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 207.0450916
• Heavy Atom Count: 14
• Complexity: 247

Purity/Quality:

99% ^*data from raw suppliers

α-(4-Chlorophenyl)-α-propionylacetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)C(C#N)C1=CC=C(C=C1)Cl
• Uses: Pyrimethamine intermediate.

Technology Process of 2-(4-Chlorophenyl)-3-oxovaleronitrile

There total 3 articles about 2-(4-Chlorophenyl)-3-oxovaleronitrile 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: 62.0%

propionyl chloride (79-03-8) + p-chlorobenzyl cyanide (140-53-4) → α-(4-chlorophenyl)-α-propionylacetonitrile (55474-40-3)

Guidance literature:

p-chlorobenzyl cyanide; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.166667h;

propionyl chloride; In tetrahydrofuran; at -78 ℃; Further stages.;

DOI:10.1021/jm010131q

Reference yield: 31.0%

Ethyl propionate (105-37-3,20741-13-3) + p-chlorobenzyl cyanide (140-53-4) → α-(4-chlorophenyl)-α-propionylacetonitrile (55474-40-3)

Guidance literature:

p-chlorobenzyl cyanide; With lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.166667h;

Ethyl propionate; In tetrahydrofuran; diethyl ether; at 20 ℃; for 72h; Further stages.;

DOI:10.1016/j.bmc.2007.04.011

Reference yield:

bromochlorobenzene (106-39-8) → α-(4-chlorophenyl)-α-propionylacetonitrile (55474-40-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: potassium methanolate / o-xylene / 2.92 h / Reflux

2.2: pH 5 - 6

With n-butyllithium; potassium methanolate; In tetrahydrofuran; o-xylene;

DOI:10.1021/acs.jafc.5b00228

upstream raw materials:

Ethyl propionate

p-chlorobenzyl cyanide

propionyl chloride

bromochlorobenzene

Downstream raw materials:

2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine

2-(4-chloro-phenyl)-3-isobutoxy-pent-2-enenitrile

5-(4-chlorophenyl)pyrimidine-2,4-diamine

3-acetoxy-2-(4-chloro-phenyl)-pent-2-enoic acid amide

Refernces

• 1、 El-Hamamsy, Mervat H.R.I.,Smith, Anthony W.,Thompson, Andrew S.,Threadgill, Michael D.. "Structure-based design, synthesis and preliminary evaluation of selective inhibitors of dihydrofolate reductase from Mycobacterium tuberculosis". . p. 4552 - 4576. Retrieved 2008/03/12.