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 ] 
• 67979-42-4 2-(4-bromo-anilino)-[1,4]naphthoquinone-4-(4-bromo-phenylimine) 
• 6628-97-3 2-(phenylamino)naphthoquinone 

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.

REACTION OF AROMATIC COMPOUNDS WITH NUCLEOPHILIC REAGENTS IN LIQUID AMMONIA. VIII. THE ORIGIN OF THE OXYGEN ATOM OF THE HYDROXY GROUP IN THE PRODUCTS FROM THE HYDROXYLATION OF 1-NITRONAPHTHALENE WITH ALKALI AND MOLECULAR OXYGEN

In the reaction of 1-nitronaphthalene witk K(18)OH and (16)O2 in liquid ammonia 1-nitro-2- and 4-nitro-1-naphthols labeled with the (18)O isotope in the hydroxyl group are formed.The ratio of the isomers and the content of the (18)O isotope depend on the ratio of 1-nitronaphthalene and alkali, on the temperature, and on the presence of moisture in the ammonia.The amount of the (18)O isotope in the hydroxylation products indicates that in contrast to the analogous reaction of nitrobenzene and its derivatives the hydroxy function of the products in this case is formed not only from the alkali but also to a significant degree from the oxygen of the O2.