5-(4-Methoxyphenyl)-5-oxovaleronitrile

Base Information

• Chemical Name: 5-(4-Methoxyphenyl)-5-oxovaleronitrile
• CAS No.: 26823-02-9
• Molecular Formula: C12H13NO2
• Molecular Weight: 203.241
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID50512300
• Wikidata: Q82371480
• Mol file: 26823-02-9.mol

Synonyms:5-(4-METHOXYPHENYL)-5-OXOVALERONITRILE;26823-02-9;5-(4-methoxyphenyl)-5-oxopentanenitrile;MFCD00448777;SCHEMBL11766726;DTXSID50512300;AKOS016022582

Chemical Property of 5-(4-Methoxyphenyl)-5-oxovaleronitrile

Chemical Property:

• Vapor Pressure: 2.03E-06mmHg at 25°C
• Boiling Point: 394.1°C at 760 mmHg
• Flash Point: 172.4°C
• PSA: 50.09000
• Density: 1.081g/cm³
• LogP: 2.57178
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 203.094628657
• Heavy Atom Count: 15
• Complexity: 246

Purity/Quality:

97% ^*data from raw suppliers

5-(4-Methoxyphenyl)-5-oxovaleronitrile 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C(=O)CCCC#N

Technology Process of 5-(4-Methoxyphenyl)-5-oxovaleronitrile

There total 12 articles about 5-(4-Methoxyphenyl)-5-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: 89.0%

4-methoxyphenylboronic acid (5720-07-0) + tert-butyl (4-cyanobutanoyl)(pyridin-2-yl)carbamate → 5-(4-methoxyphenyl)-5-oxopentanenitrile (26823-02-9)

Guidance literature:

With palladium diacetate; potassium carbonate; tricyclohexylphosphine; In 1,4-dioxane; at 70 ℃; for 8h; Inert atmosphere;

DOI:10.1002/ejoc.201901396

Reference yield: 85.0%

Glutaronitrile (544-13-8) + 4-methoxyphenylboronic acid (5720-07-0) → 5-(4-methoxyphenyl)-5-oxopentanenitrile (26823-02-9)

Guidance literature:

With [2,2]bipyridinyl; palladium(II) acetylacetonate; toluene-4-sulfonic acid; In water; toluene; at 80 ℃; for 24h; Schlenk technique;

DOI:10.1021/acs.joc.9b02999

Reference yield: 76.0%

cyclobutanone O-acetyl oxime + 4-methoxy-benzoyl chloride (100-07-2) → 5-(4-methoxyphenyl)-5-oxopentanenitrile (26823-02-9)

Guidance literature:

With bis(acetylacetonate)nickel(II); manganese; Bathocuproine; In N,N-dimethyl-formamide; at -55 ℃; for 24h;

DOI:10.1021/acscatal.8b03930

upstream raw materials:

cyanoacetic acid tert-butyl ester

3-(dimethylamino)-1-(4-methoxyphenyl)propan-1-one

2-Cyan-ethyl-malonsaeure

4-methoxy-benzoyl chloride

Downstream raw materials:

α-hydroxy-α-(p-methoxyphenyl)cyclopentanone

(S)-2-hydroxy-2-(4-methoxyphenyl)cyclopentanone

4-((4aS,5S,9bS)-7-Methoxy-2,3,4,4a,5,9b-hexahydro-1H-indeno[1,2-b]pyridin-5-yl)-phenylamine

(4aR,5S,9bR)-5-(4-Amino-phenyl)-2,3,4,4a,5,9b-hexahydro-1H-indeno[1,2-b]pyridin-7-ol

Refernces

• 1、 Mai, Wen-Peng,Liu, Yang,Sui, Hong-Dai,Xiao, Yong-Mei,Mao, Pu,Lu, Kui. "A Novel Ketonitrile Synthesis by Palladium-Catalyzed Carbonylative Coupling Reactions of Amides with Arylboronic Acids". supporting information. p. 7814 - 7819. Retrieved 2019/12/24.
• 2、 Ren, Rongguo,Wu, Zhen,Xu, Yan,Zhu, Chen. "C-C Bond-Forming Strategy by Manganese-Catalyzed Oxidative Ring-Opening Cyanation and Ethynylation of Cyclobutanol Derivatives". supporting information. p. 2866 - 2869. Retrieved 2016/02/27.