4965-30-4

Basic information

• Product Name: 1,4-Naphthoquinone 1-oxime
• Synonyms: 1,4-Naphthoquinone 1-oxime;1,4-Naphthoquinone monoxime;1,4-Naphthoquinoneoxime;4-(Hydroxyimino)naphthalen-1(4H)-one;4-Hydroxyiminonaphthalen-1(4H)-one;Naphthoquinone oxime
• CAS NO: 4965-30-4
• Molecular Formula: C₁₀H₇NO₂
• Molecular Weight: 173.1681
• Mol File: 4965-30-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 382.7°Cat760mmHg
• Flash Point: 185.3°C
• Appearance: /
• Density: 1.27g/cm³
• PKA: 10.20±0.20(Predicted)
• CAS DataBase Reference: 1,4-Naphthoquinone 1-oxime(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Naphthoquinone 1-oxime(4965-30-4)
• EPA Substance Registry System: 1,4-Naphthoquinone 1-oxime(4965-30-4)

Safety Data

• Hazardous Substances Data: 4965-30-4(Hazardous Substances Data)

Usage

Physical state

Yellow solid

Solubility

Sparingly soluble in water, more soluble in organic solvents

Derivative of

Naphthoquinone

Common use

Reagent in organic synthesis

Biological activities

Inhibits growth of certain cancer cells, antioxidant properties

Potential applications

Treatment of diseases such as malaria and tuberculosis

Versatility

Range of potential applications in various fields

Upstream product

• 90-15-3 α-naphthol 
• 181417-84-5 ethyl-(4-nitroso-[1]naphthyl)-amine 
• 104996-53-4 dimethyl-(4-nitroso-[1]naphthyl)-amine 
• 86-57-7 1-Nitronaphthalene 
• 7664-93-9 sulfuric acid 
• 64-17-5 ethanol 

Downstream Products

• 605-69-6 1-hydroxy-2,4-dinitronaphthalene 
• 21720-68-3 2-(phenylamino)-4-(phenylimino)-1(4H)-naphthalenone 
• 116665-65-7 2-(4-nitro-anilino)-[1,4]naphthoquinone-4-(4-nitro-phenylimine) 
• 133168-11-3 [1,4]naphthoquinone-mono-[O-(2,4-dinitro-phenyl)-oxime ] 
• 6628-97-3 2-(phenylamino)naphthoquinone 
• 67979-42-4 2-(4-bromo-anilino)-[1,4]naphthoquinone-4-(4-bromo-phenylimine) 

Relevant articles and documents

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.

Light-Induced Self-Nitrosation of Polycyclic Phenols with Nitrosamine. Excited State Proton Transfer

Photoexcitation of polycyclic phenols in the presence of N-nitrosodimethylamine caused the self-nitrosation of the phenols to give 1,2- or 1,4-quinone monooximes.With use of naphthols as models, the key step of the photonitrosation was shown to be a dual sensitization process from the lowest singlet excited state of naphthols by proton transfer followed by energy migration within an exciplex to cause the known homolysis of the nitrosamine; it is assumed that the resulting radical species undergo nitrosation of naphtholates.The crucial requirement of the excited state proton transfer (ESPT) reaction is established by quenching of the photonitrosation by general bases, such as water and TEA, with quenching rate constants close to those of naphthol fluorescence by these bases.