186194-64-9

Basic information

• Product Name: 2,5-Cyclohexadiene-1,4-dione,2-methoxy-,1-oxime,(E)-(9CI)
• Synonyms: 2,5-Cyclohexadiene-1,4-dione,2-methoxy-,1-oxime,(E)-(9CI)
• CAS NO: 186194-64-9
• Molecular Formula: C7H7NO3
• Molecular Weight: 0
• Product Categories: METHOXY
• Mol File: 186194-64-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,5-Cyclohexadiene-1,4-dione,2-methoxy-,1-oxime,(E)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Cyclohexadiene-1,4-dione,2-methoxy-,1-oxime,(E)-(9CI)(186194-64-9)
• EPA Substance Registry System: 2,5-Cyclohexadiene-1,4-dione,2-methoxy-,1-oxime,(E)-(9CI)(186194-64-9)

Safety Data

• Hazardous Substances Data: 186194-64-9(Hazardous Substances Data)

Usage

Structure

E-configuration

Parent Compound

2,5-Cyclohexadiene-1,4-dione (benzoquinone)

Applications

Medicinal and pharmaceutical purposes
Antioxidant properties
Treatment of various diseases
Synthesis of organic compounds
Applications in organic chemistry

Upstream product

• 150-19-6 O-methylresorcine 
• 67-56-1 methanol 
• 458-56-0 3-fluoro-4-nitroso-anisole 
• 446-38-8 2-fluoro-4-methoxy-1-nitro-benzene 
• 394-41-2 3-fluoro-4-nitrophenol 
• 458-52-6 2-fluoro-4-(methoxy)aniline 

Downstream Products

• 61638-01-5 4-Amino-3-methoxyphenol 

Relevant articles and documents

3-Methoxy-1,4-benzoquinone 4-oxime

The crystal structure of the title compound, C7H7NO3, shows a strong quinoid character. The oximic function is anti with respect to the methoxy group so that no intramolecular hydrogen bonds involving the acidic H atom are formed, instead a strong intermolecular interaction is favoured. Two molecules are present in the asymmetric unit and they show no significant differences in their bond lengths and angles, but they do have different packing interactions.

Nitrosation of phenolic substrates under mildly basic conditions: Selective preparation of p-quinone monooximes and their antiviral activities

Nitrosation of 3-methoxyphenol and 1-naphthol were examined under both acidic (NaNO2-EtCO2H-H2O) and basic (i-AmNO2-K2CO3-DMF) conditions. Acidic nitrosations afforded ortho-directed products, whereas para-directed nitrosations were observed under basic conditions to yield p-quinone monooximes. The basic para-directed nitrosation was further examined using 15 phenols, two naphthols, and four phenolic heterocyclics. A one-pot operation of the basic nitrosation followed by methylation with dimethyl sulfate gave the corresponding methyl ethers in high yield. Two p-quinone monooximes derived from 3-methoxyphenol and 8-hydroxyquinoline showed a moderate activity against HSV-1, and the latter oxime was also effective against HSV-2. On the other hand, p-quinone monooximes derived from methyl salicylate, 1-naphthol, 7-hydroxy-2-methylbenzo[b]furan, and 8-hydroxycoumarin showed the comparable activity to that of DDI against HIV-1.