3-(4-Methoxyphenyl)oxirane-2,2-dicarbonitrile

Base Information

• Chemical Name: 3-(4-Methoxyphenyl)oxirane-2,2-dicarbonitrile
• CAS No.: 33441-62-2
• Molecular Formula: C11H8N2O2
• Molecular Weight: 200.197
• DSSTox Substance ID: DTXSID80483099
• Nikkaji Number: J519.221H
• Mol file: 33441-62-2.mol

Synonyms:3-(4-Methoxyphenyl)oxirane-2,2-dicarbonitrile;33441-62-2;2,2-Oxiranedicarbonitrile, 3-(4-methoxyphenyl)-;DTXSID80483099

Chemical Property of 3-(4-Methoxyphenyl)oxirane-2,2-dicarbonitrile

Chemical Property:

• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 200.058577502
• Heavy Atom Count: 15
• Complexity: 324

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C2C(O2)(C#N)C#N

Technology Process of 3-(4-Methoxyphenyl)oxirane-2,2-dicarbonitrile

There total 4 articles about 3-(4-Methoxyphenyl)oxirane-2,2-dicarbonitrile 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: 75.0%

2-(4-methoxyphenylmethylene)malononitrile (2826-26-8) → 3-(4-methoxyphenyl)oxirane-2,2-dicarbonitrile (33441-62-2)

Guidance literature:

With calcium hypochlorite; In neat (no solvent); at 20 ℃; for 2.5h; Milling;

DOI:10.1016/j.tetlet.2018.05.077

Reference yield: 62.0%

4-methoxy-benzaldehyde (123-11-5) + malononitrile (109-77-3) → 3-(4-methoxyphenyl)oxirane-2,2-dicarbonitrile (33441-62-2)

Guidance literature:

With sodium hypochlorite; aluminum oxide; In acetonitrile; for 1.5h; Ambient temperature;

DOI:10.1055/s-1987-28104

Reference yield:

4-methoxy-benzaldehyde (123-11-5) → 3-(4-methoxyphenyl)oxirane-2,2-dicarbonitrile (33441-62-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Novozym 435 / N,N-dimethyl-formamide / 12 h / 50 °C / Green chemistry; Enzymatic reaction

2: Novozym 435; urea hydrogen peroxide adduct / N,N-dimethyl-formamide; ethyl acetate / 3 h / 50 °C / Green chemistry

With Novozym 435; urea hydrogen peroxide adduct; In ethyl acetate; N,N-dimethyl-formamide; 1: |Knoevenagel Condensation;

DOI:10.1002/ejoc.201501501

upstream raw materials:

4-methoxy-benzaldehyde

malononitrile

2-(4-methoxyphenylmethylene)malononitrile

Downstream raw materials:

5-(4-methoxy-phenyl)-thiazol-4-one

4-(4-chloro-phenyl)-2,3-bis-(4-methoxy-phenyl)-oxazolidine-5,5-dicarbonitrile

2-(4-methoxy-phenyl)-3,4-diphenyl-oxazolidine-5,5-dicarbonitrile

5-(4-methoxy-phenyl)-2-phenyl-thiazol-4-one