4023-82-9

Basic information

• Product Name: 1-(4-nitrophenyl)butane-1,3-dione
• Synonyms: 1-(4-nitrophenyl)butane-1,3-dione
• CAS NO: 4023-82-9
• Molecular Formula: C₁₀H₉NO₄
• Molecular Weight: 207.1828
• Mol File: 4023-82-9.mol

Chemical Properties

• Boiling Point: 345.8°Cat760mmHg
• Flash Point: 166.8°C
• Appearance: /
• Density: 1.271g/cm³
• Vapor Pressure: 6.02E-05mmHg at 25°C
• Refractive Index: 1.552
• CAS DataBase Reference: 1-(4-nitrophenyl)butane-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-nitrophenyl)butane-1,3-dione(4023-82-9)
• EPA Substance Registry System: 1-(4-nitrophenyl)butane-1,3-dione(4023-82-9)

Safety Data

• Hazardous Substances Data: 4023-82-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-nitrophenyl)butane-1,3-dione is utilized as an intermediate in the synthesis of a wide range of pharmaceuticals. Its unique chemical structure allows for the creation of diverse medicinal compounds, contributing to the development of new treatments and therapies.
Used in Dye and Perfume Industry:
1-(4-nitrophenyl)butane-1,3-dione also serves as a crucial intermediate in the production of various dyes and perfumes. Its ability to form different chemical structures makes it a valuable asset in the creation of vibrant colors and fragrant scents.
Used in Organic Chemistry:
1-(4-nitrophenyl)butane-1,3-dione is employed as a reagent in organic chemistry reactions. Its participation in these reactions facilitates the synthesis of other organic compounds, further expanding its utility in the chemical realm.
Used as a Precursor:
In addition to its direct applications, p-nitroacetophenone is used as a precursor in the production of other organic compounds. This role highlights its versatility and importance in the synthesis of a broader range of chemical products.
Caution:
Given its moderately hazardous nature, 1-(4-nitrophenyl)butane-1,3-dione should be handled with care to minimize potential health and environmental impacts. Proper safety measures and handling protocols are essential when working with this compound.

InChI:InChI=1/C10H9NO4/c1-7(12)6-10(13)8-2-4-9(5-3-8)11(14)15/h2-5H,6H2,1H3

Upstream product

• 108-24-7 acetic anhydride 
• 100-19-6 (4-nitrophenyl)ethanone 
• 108-05-4 vinyl acetate 
• 122-04-3 4-nitro-benzoyl chloride 
• 123-54-6 acetylacetone 
• 99-77-4 ethyl 4-nitrobenzoate 
• 67-64-1 acetone 
• 13557-37-4 ethyl-2-(4-nitrobenzoyl)-3-oxobutanoate 
• 13361-47-2 1-(4-nitro-benzoyl)-1H-benzoimidazole 
• 7664-93-9 sulfuric acid 
• 60-29-7 diethyl ether 
• 6048-20-0 4-nitrobenzoyl cyanide 
• 555-16-8 4-nitrobenzaldehdye 
• 147-85-3 L-proline 

Downstream Products

• 65124-91-6 (1E,2E)-1,2-bis(1-(4-nitrophenyl)ethylidene)hydrazine 
• 100-19-6 (4-nitrophenyl)ethanone 
• 108718-62-3 3-methyl-5-(4-nitrophenyl)-1-phenylpyrazole 
• 13298-55-0 2-diazo-1-(4-nitrophenyl)butane-1,3-dione 
• 28873-18-9 2-methyl-4-(4-nitro-phenyl)-thiopyrano[2,3-b]indole 
• 95346-61-5 C₁₆H₁₁N₄O₁₀^(1-) 
• 82366-16-3 4-Dimethylamino-benzoic acid N'-[(Z)-1-methyl-3-(4-nitro-phenyl)-3-oxo-propenyl]-hydrazide 
• 94487-88-4 3-methyl-5-(4-nitrophenyl)pyrazole 
• 343956-75-2 4-Bromo-1-(4-nitro-phenyl)-butane-1,3-dione 
• 102252-95-9 3-amino-1-(4-nitrophenyl)-2-buten-1-one 
• 82366-09-4 Benzoic acid N'-[(Z)-1-methyl-3-(4-nitro-phenyl)-3-oxo-propenyl]-hydrazide 
• 82366-15-2 4-Nitro-benzoic acid N'-[(Z)-1-methyl-3-(4-nitro-phenyl)-3-oxo-propenyl]-hydrazide 
• 139643-00-8 (Z)-3-(N',N'-Dimethyl-hydrazino)-1-(4-nitro-phenyl)-but-2-en-1-one 
• 7642-33-3 1-(buta-1,3-diyn-1-yl)-4-nitrobenzene 

Relevant articles and documents

A 1, 3 - dicarbonyl compound synthesis method

The invention discloses a synthetic method for 1,3-dicarbonyl compound, which belongs to the technical field of organic synthesis of intermediates. The method comprises the following concrete steps: (1) adding acetone, aromatic aldehyde, t-butyl hydropero

Direct synthesis of 1,3-dicarbonyl compounds via radical coupling of aldehydes with ketones under metal-free conditions

An efficient approach for the synthesis of 1,3-diketones from aldehydes and ketones has been developed using Bu4NI (TBAI) as the catalyst. In the presence of DTBP-TBHP/p-TsOH, aldehydes undergo radical coupling with ketones to provide the desired products in moderate to high yields at 120 °C. Although various substituents on the aromatic ring of aldehydes are well tolerable under the standard reaction conditions, the protocol is limited by the scope of ketones. The method exhibits advantages in terms of the easy access of the starting materials, operational simplicity, functional group tolerance, and the absence of metal catalyst.

Strategy for the synthesis of pyridazine heterocycles and their derivatives

The first synthesis of novel fused pyridazines has been realized starting from 1,3-diketones involving a Diaza-Wittig reaction as a key step. A convenient strategy was elaborated to access versatile pyridazine derivatives allowing the variation of substituents at position 6 of the heterocyclic ring. In a first part, pyridazines bearing an ester group were synthesized as a model to evaluate the methodology. In a second part, an improved procedure has been used for the synthesis of pyridazines bearing a ketone group and different methods of cyclization were carried out, leading to several hitherto unknown biheterocyclic compounds. This reaction scheme represents an attractive methodology for the synthesis of novel fused pyridazine derivatives.

Direct route to 1,3-diketones by palladium-catalyzed carbonylative coupling of aryl halides with acetylacetone

Man up your magnesium! By employing a MgCl2/Et3N system, aryl diketones can be generated from the Pd-catalyzed carbonylative α-arylation of acetylacetone with aryl bromides (see scheme). The method is ideal for the introduction of carbon isotopes into more complex structures, since only stoichiometric amounts of carbon monoxide are employed. Copyright

High-yielding oxidation of β-hydroxyketones to β-diketones using o-Iodoxybenzoic acid

The oxidation of β-hydroxyketones to β-diketones was systematically investigated. o-Iodoxybenzoic acid (IBX) was found to be efficient, operationally easy, and superior to other common oxidants. The reaction is suitable for milligram- to gram-scale oxidations.

Albumin-directed stereoselective reduction of 1,3-diketones and β-hydroxyketones to anti diols

The reduction of 1,3-diketones and β-hydroxyketones with NaBH 4 in aqueous acetonitrile is highly stereoselective in the presence of stoichiometric amounts of bovine or human albumin, giving anti 1,3-diols with d.e. up to 96%. The same reaction, without albumin, gives syn and anti 1,3-diols in approximately 1:1 ratio. The presence of an aromatic carbonyl group is essential for diastereoselectivity in the NaBH4/albumin reduction of both 1,3-diketones and β-hydroxyketones. Thus, 3-hydroxy-1-(p-tolyl)-1- butanone is stereoselectively reduced in the presence of albumin, while reduction of its isomer 4-(p-tolyl)-4-hydroxy-2-butanone is not stereoselective. The albumin-controlled reduction is not stereospecific as both enantiomers of 1-aryl-3-hydroxy-1-butanones are reduced to diols with identical stereoselectivities. Circular dichroism of the bound substrates confirms that aromatic ketones are recognized by the protein's IIA binding site. Binding studies also suggest that 1,3-diketones are recognized in their enol form. From the effect of pH on binding of a diketone it is concluded that, in the complex with the substrate, ionizable residues His242 and Lys199 are in the neutral and protonated forms, respectively. A homology model of BSA was obtained and docking of model substrates confirms the preference of the protein for aromatic ketones. Modelling of the complexes with the substrates also allows us to propose a mechanism for the reduction of 1,3-diketones in which the chemoselective reduction of the first (aliphatic) carbonyl is followed by the diastereoselective reduction of the second (aromatic) carbonyl. The role of albumin is thus a combination of chemo- and stereocontrol.

Electron-deficient aryl β-diketones: Synthesis and novel tautomeric preferences

Fluorinated aryl β-diketones were prepared using Claisen and electrophilic fluorination methods. The keto-enol and enol-enol tautomerism of these compounds were examined in the solid state, as neat liquids and in polar, aprotic solution by crystallography and spectroscopy. Neat-liquid spectroscopic measurements as well as single crystal X-ray crystallographic results for selected electron-deficient aryl β-diketones suggest a single, chelated cis-enol isomer that is conjugated with the aryl ring. In polar aprotic solvents, nonfluorinated aryl β-diketones equilibrate rapidly from the chelated cis-enol form to a tautomeric mixture of cis-chelated enol and a substantial proportion of the diketone form, trifluoromethylated aryl β-diketones show only limited equilibration from the chelated cis-enol to the diketone form, with 2-fluoro-1-aryl β-diketones again displaying only the diketonic form.

Highly efficient indium(III)-mediated cyclisation of 5-hydroxy-1,3- diketones to 2,3-dihydro-4H-pyran-4-ones; Mechanistic insights from in situ Fourier transform infrared spectroscopy

5-Hydroxy-1,3-diketones have been synthesised in a facile one-pot reaction from the treatment of acid chlorides with non-substituted ketones and LiHMDS. Subsequent cyclisation to 2,3-dihydro-4H-pyran-4-ones occurs rapidly and in high yield (89-99%) when mediated by anhydrous indium(iii) chloride. A spectroscopic study of the reaction using in situ Fourier transform infrared (FTIR) spectroscopy has shown the reaction to be highly dependent on temperature, metal complex formation and InCl3 concentration. Since the reaction is deactivated by the precipitation of [InCl3·(H 2O)3], the concurrent use of a stronger drying agent, such as molecular sieves 4 A or anhydrous MgSO4, allows the reaction to be successfully carried out at relatively low loadings of InCl 3 (1-10%). In their absence, the optimum reaction conditions were found to be a diketone:InCl3 ratio of 3:1 in toluene, and a reaction temperature of 80 °C.

The first example of molecularly imprinted nanogels with aldolase type I activity

The molecular-imprinting approach was used to obtain a nanogel preparation capable of catalysing the cross-aldol reaction between 4-nitrobenzaldehyde and acetone. A polymerisable proline derivative was used as the functional monomer to mimic the enamine-b

Seebach's oxazolidinone is a good catalyst for aldol reactions

Seebach's proline-derived oxazolidinone 2d overcomes (S)-proline and is at least as efficient as (S)-5-(pyrrolidin-2-yl)tetrazole in several organocatalytic aldol reactions examined. A quick exchange takes place between 2d and carbonyl compounds that gives new bicyclic oxazolidinones, in equilibrium with the very minor active species (enamines). Maximum yields of the aldols (β-hydroxy ketones) were achieved after 1-4 h when, with proline, they are attained after 30-48 h.