81860-68-6

Basic information

• Product Name: Oxiranecarbonitrile, 3-(4-methoxyphenyl)-
• CAS NO: 81860-68-6
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Mol File: 81860-68-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Oxiranecarbonitrile, 3-(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxiranecarbonitrile, 3-(4-methoxyphenyl)-(81860-68-6)
• EPA Substance Registry System: Oxiranecarbonitrile, 3-(4-methoxyphenyl)-(81860-68-6)

Safety Data

• Hazardous Substances Data: 81860-68-6(Hazardous Substances Data)

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 107-14-2 chloroacetonitrile 
• 14482-11-2 (E)-p-methoxycinnamonitrile 
• 59354-24-4 chloroacetonitrile 

Downstream Products

• 96125-49-4 methyl trans-3-(4-methoxyphenyl)glycidate 
• 42245-42-1 methyl (2-RS,3-SR)-2,3-epoxy-3-(4-methoxyphenyl)propanoate 
• 98421-22-8 5-<2-<<2-(4-methoxyphenyl)-2-hydroxy-1-cyanoethyl>amino>ethyl>-8-methoxycarbostyril 
• 104-01-8 4-Methoxyphenylacetic acid 
• 94592-42-4 8-hydroxy-5-<2-<<2-(4-hydroxyphenyl)ethyl>-n-propylamino>ethyl>carbostyril 
• 94592-43-5 8-hydroxy-5-<2-<<2-(4-hydroxyphenyl)ethyl>amino>ethyl>carbostyril hydrobromide 
• 94592-39-9 5-<2-<<2-(4-methoxyphenyl)-2-hydroxyethyl>amino>ethyl>-8-methoxycarbostyril 
• 94592-41-3 8-methoxy-5-<2-<<2-(4-hydroxyphenyl)ethyl>-n-propylamino>ethyl>carbostyril 
• 94592-40-2 5-<2-<<2-(4-methoxyphenyl)ethyl>amino>ethyl>-8-methoxycarbostyril 
• 344256-01-5 5-(4-Methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolane-4-carbonitrile 
• 73377-97-6 (2R,3S)-3-(4-Methoxy-phenyl)-1,2,3,4-tetrahydro-quinoxaline-2-carbonitrile 
• 73384-19-7 (2S,3R)-3-(4-Methoxy-phenyl)-6,7-dimethyl-1,2,3,4-tetrahydro-quinoxaline-2-carbonitrile 
• 81860-76-6 2-(4-methoxyphenyl)-1-(piperidin-1-yl)ethan-1-one 

Relevant articles and documents

BF3·OEt2-promoted tandem Meinwald rearrangement and nucleophilic substitution of oxiranecarbonitriles

Tandem Meinwald rearrangement and nucleophilic substitution of oxiranenitriles was realized. Arylacetic acid derivatives were readily synthesized from 3-aryloxirane-2-carbonitriles with amines, alcohols, or water in the presence of boron trifluoride under microwave irradiation, and the designed synthetic strategy includes introducing a cyano leaving group into arylepoxides and capturing the in situ generated toxic cyanide with boron trifluoride, making the reaction efficient, safe, and environmentally benign. The reaction occurs through an acid-promoted Meinwald rearrangement, producing arylacetyl cyanides, followed by an addition-elimination process with nitrogen or oxygen-containing nucleophilic amines, alcohols or water. The current method provides a new application of the tandem Meinwald rearrangement.

REACTION OF 4-SUBSTITUTED BENZALDEHYDES AND ACETOPHENONES WITH CHLOROACETONITRILE

Under conditions of phase-transfer catalysis or in homogeneous solution of potassium tert-butoxide the title compounds give stereoisomeric mixtures of substituted 2,3-epoxy nitriles III and IV.Alkaline hydrolysis of epoxy nitriles IV afforded the corresponding 2-arylpropanals in low yields.On treatment with methanol and potassium carbonate, epoxy nitriles III and IV were converted into epoxy esters in good yields.

Synthesis of 4-cyano-1,3-dioxolanes from 2,3-epoxynitriles

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